59 Best Things to Do in Chicago in 2024 (By a Local)

by Mary Howard
- June 15, 2024

When it comes to things to do in Chicago, Illinois, this Midwestern destination is practically overflowing.

The city offers an incredible food scene, vibrant arts and culture, access to beautiful Lake Michigan, fantastic areas to stay, and is one of the best sports towns in America (and this is just for starters). At the end of the day, there’s something for everyone in Chicago.

No matter your reason for visiting, if you’ve never been to the Windy City then you’re in for a treat – Chicago has it all. I mean, after just one trip, I found myself packing up and moving here.

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Table of Contents

59 Best Things to Do in Chicago

Explore Chicago’s Neighborhoods

Visit a few of Chicago’s many diverse and unique neighborhoods.

📍 18 Best Chicago Neighborhoods

You may have heard that Chicago is a city of neighborhoods. Although the boundaries and names of each neighborhood are a bit subjective, the city is distinctly made up of 77 community areas; each one with its own unique flair.

If you’ve never been to Chicago, it can be tempting to spend all your time in the city’s downtown Loop. And while the Loop is an area worth spending time in for sightseeing, shake things up by exploring different neighborhoods in Chicago.

Head to Lincoln Park for a charming downtown feel. There are tons of shops to browse, and some of the best restaurants in Chicago to try. Plus, Lincoln Park (the actual park) and the zoo are nearby.

West Town is another great area to explore and has a great “local” vibe to it. Smaller neighborhoods like Wicker Park, Bucktown, and Ukrainian Village can all be found here.

Lastly, Gold Coast is a great neighborhood for some history and beautiful architecture. Take a walk through the area and admire the beautiful brownstone homes, which are only a short walk to the lake.

Millennium Park

Go sightseeing in Chicago’s downtown Loop.

📍 Google Maps | Phone: (312) 742-1168 | Millennium Park Website | Hours: 6 am – 11 pm daily | Entrance: Free

Situated in the loop and housed within the larger Grant Park is Chicago’s Millennium Park. This park, which is also connected to Maggie Daley Park, is one of Chicago’s most iconic spots.

Here, you can enjoy activities and witness the city skyline up close. Most importantly, Millennium Park is home to Cloud Gate, or, as it’s better known, “The Bean.”

Millennium Park has a lot more to offer besides a picture with the Bean, though. All year round, you can walk the park, enjoy public art, and witness images at Crown Fountain – an interactive video sculpture.

In the winter, you can go ice skating just below the Bean or at the nearby Maggie Daley ice skating ribbon.

In the summer, enjoy outdoor concerts and Chicago festivals. Favorites include the Chicago Blues Festival and Millennium Park Summer Music Series, which take place at Jay Pritzker Pavilion.

👉 Did You Know? Although Cloud Gate is stainless steel, artist Anish Kapoor drew inspiration from liquid mercury. The shiny, mirror-like surface was also meant to reflect the Chicago skyline.

Cloud Gate (“The Bean”)

Chicago’s most iconic landmark—a mirror-like art sculpture that locals call “The Bean.”

📍 Google Maps | Website | Hours: 6 am – 11 pm daily | Entrance: Free

Cloud Gate, more commonly referred to as “The Bean,” is Chicago’s most identifiable landmark. This giant structure is located in downtown’s Millennium Park. The Bean is best known for its mirror-like surface, which reflects images of the Chicago skyline above.

The Bean is a fun experience for first-time visitors and I recommend stopping by for a quick picture. Visit in the morning or early evening for fewer crowds.

The Art Institute of Chicago

Enjoy a world-class collection of art in downtown Chicago.

📍 Google Maps | Phone: (312) 443-3600 | Art Institute Website | Hours: 11 am – 5 pm Fri – Mon, 11 am – 8 pm Thu, Closed Tue & Wed | Entrance: $32 for adults, $26 for seniors and students, Free for children (discounts available for Illinois & Chicago residents)

Located in the Loop and just south of Millennium Park is the Art Institute of Chicago. This world-class museum features thousands of artworks from around the world, spanning centuries and styles. Think of artists like Van Gogh, Monet, and Picasso, just to name a few.

Plan to spend at least a few hours wandering the Art Institute. The historic building has four levels in total, with numerous wings and exhibitions to explore. The museum is also family-friendly.

Do note that because of its size, young children and seniors may become tired. Tickets can be purchased online and in advance, but they may also be purchased on-site.

👉 Pro Tip: I’ve found that one of the best ways to see and navigate a museum of this size is to start on the top floor and work your way down.

Wrigley Field

Attend a baseball game at one of America’s most famous ballparks.

📍 Google Maps | Phone: (773) 404-2827 | Wrigley Field Website | Hours: On game days, gates open 2 hours before the first pitch | Tickets: Ranging from $10 – $300

Chicagoans take their sports seriously, and this obviously includes Wrigley Field – home of the Chicago Cubs. Built in 1914 and located in the neighborhood of Wrigleyville, this famous stadium is the second oldest Major League baseball field in America.

Throughout its history, the ballpark has witnessed so many historic moments, from Babe Ruth “calling his shot” in 1932, to “reversing the curse” in 2016. Not to mention, the Cubs have won three World Series titles and longstanding traditions are a key part of the experience.

The stadium itself has brick walls covered in ivy, as well as a beloved red marquee on display out front. As an ode to the beginnings of baseball, the scoreboard is manually operated, too.

Order some snacks or Chicago-style hot dogs if that’s your style. Although, to avoid some craziness, plan on getting lunch and drinks before your game.

🚗 How to Get There: Parking can be a nightmare so a better option is to use the CTA Red Line or rideshare options for transportation. Just note that the train will most likely still be packed and rideshares can get pricey around game time.

Take an Architecture Cruise

Journey through Chicago’s history and architecture and enjoy amazing downtown views.

For visitors of all ages and interests, an architecture cruise is a must in Chicago. You can expect to sit back and relax while a guide talks you through Chicago history and the iconic buildings that line the Chicago River.

What’s great about this type of tour is that you can take in the sights and snap pictures from the comfort of your seat. You’ll leave with a better understanding of the city, its history, architecture, and more. Tours last about an hour long.

Lakefront Trail

Run, walk, or bike along beautiful Lake Michigan on this 18-mile urban trail.

Part of what makes Chicago so unique is its access to Lake Michigan. In the winter, part of the lake freezes over and creates icy waves along the shore. In the summer, the lake provides a welcome escape from the heat.

If you plan on visiting during the warmer months, set aside some time for the Lakefront Trail. This paved path runs for 18 miles along the city and shoreline, providing incredible views. The trail is free to everyone and perfect for walking, running, and biking.

Chicago Riverwalk

Take a leisurely stroll through the heart of Chicago.

📍 Google Maps | Phone: (877) 300-6746 | Chicago Riverwalk Website | Hours: 6 am – 11 pm daily | Entrance: Free

The Chicago Riverwalk is a 1.25-mile urban trail that lines the Chicago River just north of the Loop. This pedestrian path is one of my favorite ways to sightsee downtown. It’s free, open year-round, and lined with restaurants, bars, cafes, shops, and more.

This is a great place to take a scenic, leisurely stroll, or sit down somewhere for a picnic or quick rest. You can access the Riverwalk via multiple entry points off of E Wacker Drive. Just head down to the river and find the signs marked “Chicago Riverwalk.”

👉 Did You Know? Every year for St. Patrick’s Day, the Chicago River is dyed green!

Chicago Sites & Attractions

Navy Pier

Enjoy a day of views, attractions, and fun for the whole family.

Just north of the Loop in the Streeterville neighborhood, Navy Pier extends out into the Lake Michigan shoreline. This pier has activities and restaurants for the whole family to enjoy, and is also a great spot for snapping some pictures of the lake and Chicago skyline.

Some of the popular activities and attractions at the pier include: Cruise tours, Centennial ferris wheel, the Chicago Children’s Museum, Chicago Shakespeare Theater, and Navy Pier Beer Garden. There is also the Polk Bros Park, where you can rest, relax, or enjoy free events and programs.

Navy Pier also offers seasonal attractions such as fireworks in the summer and Light Up The Lake in the winter (an indoor light garden).

📚 See our full Navy Pier guide to get planning.

Magnificent Mile

Shop your heart out and take in the sights.

📍 Google Maps | Phone: (312) 642-3570 | Magnificent Mile Website | Hours: Open daily, shop hours may vary | Entrance: Free

If you’re looking to do some luxury shopping and hit up those big-name stores, then pay a visit to the Magnificent Mile. Technically named North Michigan Avenue, this mile-long stretch is packed with shops, restaurants, luxury hotels, and more.

Although a bit touristy, it’s worth visiting for anyone with an itch to shop. Not to mention, it’s close to the lakefront and only a short walk to the Chicago River and River North neighborhood for some more shopping.

While you browse the Magnificent Mile, be sure to take in some of the historic buildings along the way like the Chicago Water Tower, Tribune Tower, and Wrigley Building.

👉 Love History? If shopping isn’t your thing and you’d rather experience the Magnificent Mile from a historical point of view, check out this Magnificent Mile Walking Tour!

Lincoln Park Zoo

Come face to face with wildlife.

📍 Google Maps | Phone: (312) 742-2000 | Lincoln Park Zoo Website | Hours: 10 am – 5 pm daily | Entrance: Free

Get up close and personal with animals at Lincoln Park Zoo. This Chicago zoo, which is free to all, is located in the heart of Lincoln Park. Almost 200 species of animals from around the world can be found here — bears, crocodiles, hippos, and everything in between.

Most habitats are designed for visitors to observe the animals in their own environment, but a few interactive opportunities are available, too. The zoo is fairly easy to navigate, so if you plan on seeing all the exhibits, plan on spending an entire afternoon here.

👉 Pro Tip: Although the Lincoln Park Zoo is free, parking can range from $20-$35. If you want to avoid this cost, then I recommend taking public transportation to the nearest train or bus stop. Or, if your accommodations are nearby, take a walk through Lincoln Park and over to the zoo.

Willis Tower Skydeck

Take in sweeping views of the city.

For breathtaking views of Chicago, head to Willis Tower in the Loop. Formerly known as Sears Tower, this 108-story building is the tallest building in all of Chicago and the second tallest building in North America.

The Willis Tower Skydeck and Ledge is located on the 103rd floor and is a family-friendly way to take in the city below. Upon entrance, you’ll weave through educational displays and exhibits designed to give you a taste of Chicago’s history. This is all leading up to the main Skydeck itself where you’ll see the city through floor-to-ceiling windows.

If you’re not afraid of heights, step out on the Ledge. This 4.3 feet glass box extends out over the city for views in every which way – on a clear day you might be able to see four states!

👉 Pro Tip? Definitely take the weather into account when visiting Willis Tower. For the best views, visit on a clear day.

360 Chicago Observation Deck

Take a tilt over Chicago.

📍 Google Maps | Phone: (888) 875-8439 | 360 Chicago Website | Hours: 9 am – 11 daily | Entrance: $44 – $58 for ages 12+, $34 – $38 for ages 3 – 11

Looking to take in the Chicago skyline from a new perspective? At the 360 Chicago Observation Deck, you can do just that.

From the 94th floor of the John Hancock Center, you’ll be met with 360-degree views of the city, lake, and surrounding areas. Because of the building’s location, you’ll have especially close views of the Magnificent Mile and Lake Shore Drive.

For an extra wow factor, take a ride on Tilt. This attraction will tilt you more than 1000 feet over the Magnificent Mile on Michigan Avenue. If you have a fear of heights, then this might not be the experience for you. But for most visitors, regardless of age, this is a unique and thrilling experience.

👉 Pro Tip: Similar to Willis Tower, I recommend visiting the John Hancock Center on a clear day. You’ll get the most out of your money and witness the best views.

Shedd Aquarium

Experience what’s under the surface.

📍 Google Maps | Phone: (312) 939-2438 | Shedd Aquarium Website | Hours: 9 am – 5 pm Mon, 9 am – 9 pm Tue, 9 am – 7 pm Wed-Sat, 9 am – 6 pm Sun | Entrance: $20 – $40 for ages 12+, $15 – $30 for ages 3 – 11, Free for ages 3 and under

In addition to the Lincoln Park Zoo, Chicago also has its own state-of-the-art aquarium. The family-friendly facility is located right on the water along Chicago Harbor. This 5-million-gallon aquarium houses aquatic life from around the world including animals native to the Great Lakes.

There is a wide variety of exhibits to explore during your visit. Popular options include the Abbott Oceanarium, Wild Reef, Caribbean Reef, and more. Children can even enjoy interactive experiences where they can touch Stingrays, Sea Stars, and Sturgeons.

Shedd Aquarium is also near the Field Museum and Adler Planetarium, in case you want to plan a whole day around these attractions.

Adler Planetarium

Travel through space and time.

📍 Google Maps | Phone: (312) 922-7827 | Adler Planetarium Website | Hours: 9 am – 4 pm Thu-Tue, 4 pm – 10 pm Wed | Entrance: $19 – $35 for adults, $8 – $24 for ages 3 – 11

Take in the universe and learn all about astronomy at Adler Planetarium. This museum and historical landmark is located on Northerly Island at the base of Chicago Harbor. This is right near the Field Museum and Shedd Aquarium.

Adler Planetarium is family-friendly and an interactive experience for everyone. Theater programs are shown every day and educational events happen throughout the year. Popular exhibits include Astronomy in Culture, Chicago’s Night Sky, Our Solar System, and more.

👉 Did You Know? Adler Planetarium was the first planetarium in America!

ART on THE MART

Watch this iconic architectural attraction light up with color and movement.

📍 Google Maps | Phone: (800) 677-6278 | ART on THE MART Website | Hours: Varies by season | Entrance: Free

ART on THE MART is the largest digital art projection in the world. It runs every night between April and December. Art collections rotate throughout the year, so there’s always a new light show to see.

I recommend making a whole evening out of ART on THE MART. Grab dinner along the river beforehand, and then find a spot to sit or stand on the Chicago Riverwalk across from the iconic building. Then, watch as thousands of light projections cast colorful, moving artworks on the facade of THE MART. It’s a truly unique experience!

Crown Fountain

A digital and interactive art display in Millennium Park.

📍 Google Maps | Phone: (312) 742-1168 | Website | Hours: 6 am – 11 pm daily | Entrance: Free

Crown Fountain is a digital art display on two 50-foot-tall towers. These towers are located in Millennium Park and are best known for displaying the “Faces of Chicago.”

These locals’ faces are meant to be a modern take on gargoyles. Similarly, water flows out of the “mouths” of the diverse faces displayed. Crown Fountain was designed by Spanish artist, Jaume Plensa. It’s a unique landmark and a nice spot to cool off during the summer.

United Center

Watch Chicago basketball, hockey, and more.

📍 Google Maps | Phone: (312) 455-4500 | United Center Website | Hours: Game and show times may vary, doors open 90 minutes prior to games | Entrance: Each event may vary

On the Near West Side of Chicago is the city’s other famous sports venue: United Center.

This indoor arena is home to the NBA’s Chicago Bulls and NHL’s Chicago Blackhawks. In addition to being a sports venue for basketball and hockey games, United Center serves as an arena for concerts and other shows – it’s also America’s largest arena.

A couple of cool things to see at the United Center include the 58 banners hanging from the ceiling (marking championship titles for both the Bulls and the Blackhawks) and the 12-foot tall bronze Michael Jordan statue.

🛏️ Need a Hotel? The Hyatt House Chicago Medical/University District has good amenities and is located close to the arena if you’re going to an event at United Center.

Chicago Museums & Cultural Attractions

👉 Pro Tip: You can also bookmark our full list of the 20 best museums in Chicago.

Museum of Science and Industry

This museum on Chicago’s South Side is one of the largest science museums in the world.

The Museum of Science and Industry (MSI) is one of Chicago’s best museums. It’s located in Jackson Park on Chicago’s South Side and is one of the largest science museums in the world.

Visitors of all ages will enjoy MSI. It’s filled with endless interactive exhibits about science, innovation, and engineering feats from around the globe and throughout history. Popular permanent exhibits include the Coal Mine, U-505 Submarine, and the Mirror Maze. But there are exciting new temporary exhibits each year.

Be sure to block out an entire morning or afternoon to visit MSI. The museum is massive.

Museum of Contemporary Art

Engage with contemporary art exhibits designed to make you think.

📍 Google Maps | Phone: (312) 280-2660 | Museum of Contemporary Art Website | Hours: 10 am – 9 pm Tue, 10 am – 5 pm Wed – Sun, Closed Mon | Entrance: $22 for adults, $14 for students, teachers, and seniors, Free for ages 18 and under

Unlike the Art Institute of Chicago, the Museum of Contemporary Art (MCA) features constantly rotating exhibitions by contemporary artists of today. I’ve been to MCA many times, and enjoy different and thought-provoking exhibitions on every visit.

This museum is family-friendly, but students and adults may especially appreciate the more nuanced, and often heavier, subject matter. Still, there is artwork for everyone to enjoy. The museum also offers live performances, events, and programs for the community. Expect to spend around an hour to two hours here.

Field Museum

Immerse yourself in some natural history.

📍 Google Maps | Phone: (312) 922-9410 | Field Museum Website | Hours: 9 am – 5 pm daily | Entrance: $18 – $27 for adults, $19 – $29 for children ages 3 – 11, Free for ages 2 and under

The Field Museum is located just south of Grant Park and is near the Shedd Aquarium and United Club Stadium. This massive museum is home to almost 40 million specimens and artifacts such as T-Rexes, meteorites, animal biology, and more.

This museum is especially family-friendly and aimed at immersing children in science and discovery. 3D movies are also shown for the whole family to learn from so plan to spend an entire morning or afternoon here.

A visit to the Field Museum is a great way to experience natural wonders and history all in one afternoon.

👉 Want to Explore More Around Chicago? Bookmark my guide to the best day trips from Chicago.

Chicago Children’s Museum

Let your kids play, learn, and explore to their hearts’ content.

📍 Google Maps | Phone: (312) 527-1000 | Chicago Children’s Museum Website | Hours: 10 am – 5 pm daily | Entrance: $21 for adults and children, Free for ages 1 and under

At the Chicago Children’s Museum, children of all ages can enjoy a space to play and learn. Located on Navy Pier, the museum itself is comprised of more than a dozen exhibits that cater to different interests and experiences.

For some math, science, and discovery, exhibits like Tinkering Lab, Skyline, and Dinosaur Expedition will allow children to tinker, build mini-skyscrapers, and even dig for dinosaur bones. At the Art Studio, children can let their imaginations soar with painting, drawing, and pottery-inspired workshops.

Additionally, children can learn practical life skills and take the lead at exhibits like Kids Town and Michael’s Museum. And for some overall fun, there are tons of exhibits for your little ones to climb, play, explore, and learn.

Chicago History Museum

Uncover Chicago’s history.

📍 Google Maps | Phone: (312) 642-4600 | Chicago History Museum Website | Hours: 9:30 am – 4:30 pm Tue – Sat, 12 – 5 pm Sun, Closed Mon | Entrance: $19 for adults, $17 for students and seniors, Free for ages 18 and under (Illinois residents)

Located right near the lake in the southeastern corner of Lincoln Park is the Chicago History Museum. One of Chicago’s oldest cultural institutions, a visit to this museum will walk you through the city’s historic past to learn about what makes Chicago, well, Chicago.

Exhibitions explore topics like freedom, democracy, and the history of Abraham Lincoln. A film is also available to learn about the city’s growth and events like the Great Chicago Fire of 1871. There’s even an exhibit for uncovering the city through the five senses.

👉 Pro Tip: If you’re a first-time visitor, I recommend stopping at the Chicago History Museum early on in your trip and planning to spend a couple of hours here. This way, you’ll have a better idea of what you’re seeing as you explore the city.

National Museum of Mexican Art

Appreciate Mexican art and culture.

📍 Google Maps | Phone: (312) 738-1503 | Museum of Mexican Art Website | Hours: 10 am – 5 pm Tue – Sun, Closed Mon | Entrance: Free

Located in the neighborhood of Pilsen, the National Museum of Mexican Art is home to one of the largest collections of Mexican art in the country. This museum, which first opened in 1987, features both permanent and rotating art exhibitions, as well as cultural performances, films, and programs.

Although the museum may be especially appreciated by members of the Mexican community, it is open to visitors of all ages and backgrounds. Visiting this museum is a great way to learn, support, and appreciate Mexico’s rich history and vibrant artwork.

Chicago Cultural Center

Learn about a historical landmark and attend free public events.

📍 Google Maps | Phone: (312) 744-5000 | Chicago Cultural Center Website | Hours: 10 am – 5 pm daily | Entrance: Free

The Chicago Cultural Center is one of Chicago’s (and the nation’s) most comprehensive cultural centers. Built in 1897, this historic Chicago landmark serves as a cultural destination for the public. The building itself has two beautiful stained-glass domes and intricate architectural details throughout, making it an absolute marvel.

The center’s main focus is bringing free events for everyone to enjoy. This includes art performances and exhibitions, lectures, and cultural events. Guided tours are also available.

If you’re interested in history, arts, and culture, then this is a good stop to make on your itinerary for Chicago.

👉 Did You Know? The building’s south dome is actually the largest stained-glass Tiffany dome in the world!

The Rookery Building

This 19th-century building in the Loop is one of Chicago’s most important landmarks.

📍 Google Maps | Phone: (312) 553-6100 | Website | Hours: 6 am – 6 pm Mon – Fri, 8 am – 2 pm Sat, Closed Sun | 🎫 Tour: $12-$17

The Rookery Building is one of Chicago’s coolest buildings. It’s a stellar example of the city’s architectural boom that followed the Great Chicago Fire of 1871. The Rookery Building is considered by many to be an “architectural masterpiece.”

The building itself was designed by Daniel Burnham and John Root. However, Chicago architect Frank Lloyd Wright had his hand in redesigning the lobby in 1905.

You don’t have to be a lover of architecture and design to appreciate how beautiful the Rookery Building is. The spiral Oriel Staircase is the top highlight for most people. It’s stunning. The Light Court lobby is beautiful, too.

DuSable Museum of African American History

Visit this compelling museum about African American history in Chicago and beyond.

a woman standing next to a statue of a young girl

📍 Google Maps | Phone: (773) 947-0600 | Website | Hours: 11 am – 4 pm Wed – Sun, Closed Mon & Tue | Entrance: $14.50 adults, $5 children

The DuSable Museum of African American History is located in Washington Park on Chicago’s South Side. This museum is one of the oldest African American museums in the country. Here, you’ll learn about African American history that happened in Chicago and beyond. The exhibits contain historic artifacts and artwork, along with thought-provoking media presentations.

For example, the DuSable Museum previously held a virtual reality exhibit on Martin Luther King Jr.’s “I Have A Dream” speech from 1963. Other exhibits have ranged from fashion objects to stories of the African diaspora.

The DuSable Museum of African American History is right next to the University of Chicago’s campus. Check out the museum while you explore the university area.

Richard H. Driehaus Museum

Explore the ornate rooms within this Gilded Age mansion and museum near the Magnificent Mile.

📍 Google Maps | Phone: (312) 482-8933 | Website | Hours: 11 am – 3 pm Wed, 11 am – 5 pm Thu & Sun, 10 am – 5 pm Fri & Sat, Closed Mon & Tue | Entrance: $20 adults, $15 seniors, $10 students, free for ages 12 and under

Richard H. Driehaus Museum is a small mansion museum in downtown Chicago, just a couple of blocks away from the Magnificent Mile. This historic Chicago building was built in 1883. It was home to Samuel and Matilda Nickerson, a wealthy and influential Chicago couple.

The Gilded Age mansion is best known for its marble detailing and ornate design. Everything is exquisite, from the stained glass windows and dome to the intricate woodworking details. A $5 guided tour is the best way to experience this historic gem.

University of Chicago

Chicago’s premier university in Hyde Park has a beautiful campus filled with Gothic architecture.

📍 Google Maps | Phone: (773) 702-1234 | Website | Entrance: Free

The University of Chicago (UC) is the Windy’s City’s premier private university. It’s located on Chicago’s South Side in Hyde Park. You don’t have to be a student to visit or appreciate the beautiful campus. It’s filled with Gothic-style architecture and other unique buildings worth checking out.

Highlights include Bond Chapel, Rockefeller Memorial Chapel, and Cobb Lecture Hall. The Joe and Rika Mansueto Library is a cool, modern building where scenes from the 2014 movie Divergent were filmed. Other highlights of UC include the Frederick C. Robie House and Smart Museum of Art.

Frederick C. Robie House

This iconic Prairie-style home in Hyde Park was designed by famed Chicago architect Frank Lloyd Wright.

📍 Google Maps | Phone: (312) 994-4000 | Website | Hours: 9:30 am – 4 pm Thu – Mon, Closed Tue & Wed | 🎫 Tour: $30

Frederick C. Robie House is an iconic landmark in terms of Chicago architecture and design. It was designed by famed Chicago architect Frank Lloyd Wright and is best known for showcasing his Midwestern Prairie style.

The Robie House, as locals call it, was built in 1910. Today, it’s a museum where you can witness this Prairie-style architecture up close. Tours show off the exterior and interior, including its unique woodwork.

Fans of architecture and design will especially appreciate visiting The Robie House. The house is also located on the University of Chicago’s campus, so be sure to wander around for more unique architectural sights.

Frank Lloyd Wright Home & Studio

This historic Prairie-style home and studio in Oak Park was designed by famous Chicago architect Frank Lloyd Wright.

The Frank Lloyd Wright Home & Studio is exactly what it sounds like: the home and studio of prominent Chicago architect, Frank Lloyd Wright. Fans of architecture and design will especially appreciate this museum.

You need to book a tour to visit. Tours are about an hour long and are led by knowledgeable guides. This is a great opportunity to learn more about Frank Lloyd Wright and his iconic Prairie-style architecture and design. The home’s unique interior details like the woodwork and use of natural light is what makes this place so cool.

This museum is located a bit outside the city in Oak Park. It’s a good place for a mini-day trip. You can reach this museum by car, but you can also take the Green Line to Oak Park.

Ernest Hemingway’s Birthplace Museum

Visit the birthplace and childhood home of famous American author Ernest Hemingway.

The Ernest Hemingway Birthplace Museum is the birthplace and childhood home of famed American author Ernest Hemingway. This is a unique place to visit if you’re interested in literature or history.

Ernest Hemingway was known for being an adventure-seeking world traveler, but his life started just outside of Chicago in Oak Park. This home and birthplace museum showcases Hemingway’s life and career. You can walk through the Victorian-style house to feel what life was like for young Hemingway and see some artifacts as well.

The Ernest Hemingway Birthplace Museum is just a stone’s throw away from the Frank Lloyd Wright Home & Studio in Oak Park. Combine both of these museums into one visit.

Outdoor Attractions in Chicago

Grant Park

Visit one of Chicago’s biggest cultural hubs.

📍 Google Maps | Phone: (312) 742-3918 | Grant Park Website | Hours: 6 am – 11 pm daily | Entrance: Free

Known as downtown Chicago’s “front lawn,” Grant Park is a cultural hub that spans over 300 acres. In many ways, it’s the central, go-to place for a nature escape downtown as it houses Millennium Park and Maggie Daley Park.

This vast green space is more than just a park, though. Some of the top attractions in Chicago all converge in this one place.

Besides Cloud Gate and everything within Millennium and Maggie Daley Parks, the Chicago Art Institute, Lakefront Trail, and Buckingham Fountain can all be found here.

And throughout the year, Grant Park also hosts a plethora of Chicago festivals including Taste of Chicago, SummerDance, and most notably, Lollapalooza.

North Avenue Beach

Spend an afternoon on Lake Michigan.

📍 Google Maps | Phone: (312) 742-5121 | North Avenue Beach Website | Hours: 11 am – 7 pm daily | Entrance: Free

If you plan on visiting in the summer, then I highly recommended planning for some beach time in Lake Michigan. For an afternoon by the water, I especially recommend North Avenue Beach.

Though it can get a bit crowded on hot days, this Chicago beach is close to downtown and falls along the Lakefront Trail. Volleyball courts and water sports rentals are available here.

North Avenue Beach also features incredible views of the city and lake. Walk out on the boardwalk to take in the picturesque Chicago skyline and bright blue water. Just note that it can get pretty windy out on the boardwalk. It is the Windy City after all.

🚗 Need some wheels? Though getting around Chicago is easily done with the transit system, I recommend renting a car with Discover Cars if you plan on venturing out of the main parts of Chicago.

Kayak the Chicago River

Paddle down the Chicago River and take in the city from a new perspective.

If you plan on visiting during the warmer months, try something a little different: kayak down the Chicago River! This is a fun activity for visitors of all ages and a unique way to experience the downtown scene.

This historic Chicago kayak tour is a particularly popular one, where you get a history tour while you paddle along the urban landscape. Tours typically last about two hours and are beginner-friendly.

Bloomingdale Trail “The 606”

Take a walk along Chicago’s urban greenway.

📍 Google Maps | Phone: (312) 742-4622 | 606 Website | Hours: 6 am – 11 pm daily | Entrance: Free

The Bloomingdale Trail, better known as “The 606,” is a 2.7 mile-long walking trail that extends west from Ridgeway Ave, and then east to Ashland Ave.

This trail, which was transformed from an old rail line, offers a refreshing outdoor escape and is perfect for runners, bikers, and anyone who wants to enjoy a nice stroll.

There are 12 entry points to reach the trail from. Depending on where you stay in Chicago, the easiest way to reach the 606 is by taking the CTA Blue Line. Damen and Western stops will bring you within walking distance of the trail itself.

If you’re looking to get a little exercise in while still enjoying the city, head to the 606!

Maggie Daley Park

A family-friendly park in downtown Chicago, home to several recreational activities.

📍 Google Maps | Phone: (312) 742-3918 | Website | Hours: 6 am – 9 pm daily | Entrance: Free

Visiting Maggie Daley Park is great if you are visiting Chicago with kids. This park is located in the northeastern corner of Grant Park and contains numerous recreational areas.

There’s a playground or “play garden,” a climbing wall, a mini golf course, tennis courts, sidewalks for biking and scootering, ice skating rinks in the winter, and picnic areas. There’s also a fieldhouse, cafe, and Cancer Survivors’ Garden.

Simply put, Maggie Daley Park is one of the best places in Chicago to let your kids play and explore freely.

Lincoln Park Conservatory

A vibrant and blooming greenhouse in Lincoln Park that’s free to visit.

a garden filled with lots of green plants

a garden filled with lots of flowers and plants

📍 Google Maps | Phone: (773) 883-7275 | Website | Hours: 10 am – 5 pm Wed – Sun, Closed Mon & Tue | Entrance: Free (online reservations required)

Lincoln Park Conservatory is a free greenhouse in Lincoln Park. It can be explored in about an hour, and it’s a great spot to visit if you’re looking for a change of scenery in the city.

The greenhouse contains different garden houses. This includes the Orchid House, Fern Room, a room for special exhibits, and the Palm House — my favorite. Be sure to reserve tickets to the Lincoln Park Conservatory online.

Alfred Caldwell Lily Pool

A hidden lily pool in Lincoln Park that’s inspired by the Midwestern prairie.

📍 Google Maps | Phone: (773) 883-7275 | Website | Entrance: Free

Alfred Caldwell Lily Pool is often overlooked in Lincoln Park. This lily pool and pavilion provide a small, but peaceful escape from the noise of the city. It was designed by landscape architect Alfred Caldwell and meant to look like a Midwestern prairie.

It’s free to visit Alfred Caldwell Lily Pool. Come here to sit, relax, and enjoy a restful moment, or even bring a book. I recommend visiting the lily pool in conjunction with the Lincoln Park Conservatory and Lincoln Park Zoo.

Garfield Park Conservatory

Experience a natural oasis just outside the city.

📍 Google Maps | Phone: (773) 638-1766 | Garfield Park Conservatory Website | Hours: 10 am – 8 pm Wed, 10 am – 5 pm Thu – Sun, Closed Mon & Tue | Entrance: Free (online reservations required)

Garfield Park Conservatory in Garfield Park is located about halfway between downtown Chicago and Oak Park. This conservatory, which is one of the largest in the country, is a beautiful place to witness nature and plants from around the world. In total, the conservatory has 2 acres of greenhouse space and 10 acres of garden.

Plan on spending around one to three hours wandering this nature oasis. Popular garden collections include the Palm House, Desert House, and Fern House. The conservatory also offers exhibit and installation events, and educational programs.

Overall, the Garfield Park Conservatory is the perfect nature escape from Chicago.

Oz Park

A serene, yet playful neighborhood park that’s great for picnicking and exploring Lincoln Park.

📍 Google Maps | Phone: (312) 742-7898 | Website | Hours: 6 am – 11 pm daily | Entrance: Free

Oz Park is a recreational park set in the heart of the Lincoln Park neighborhood. Its Wizard of Oz theme makes it fun for families, but for simply relaxing, too.

Mostly locals frequent the open green spaces, benches, and walking paths at Oz Park. There are also tennis/pickleball courts and baseball and soccer fields to enjoy.

Food & Drink in Chicago

Lou Malnati’s Pizzeria

Pizza the Chicagoan way.

📍 Google Maps | Phone: (312) 828-9800 | Lou Malnati’s Website | Hours: Vary by location

When it comes to food, deep-dish pizza is a distinctly Chicagoan thing. This style of pizza is sometimes referred to as “Chicago-style pizza” and is made with a thick crust, and stacked with layers of sauce, cheese, and toppings. The layers are even placed on the dough backward, with cheese placed first and sauce topped off last.

If you’re looking to taste a classic deep dish, then head to Lou Malnati’s. They have multiple locations and are one of the oldest deep-dish pizzerias in Chicago. Their pizzas are known for their made-from-scratch, flaky, buttery crusts, and fresh ingredients.

This is a great option that’s both casual and family-friendly.

👉 Pro Tip: Deep dish pizza can take a while to bake, so plan for a little extra time.

Time Out Market

Options for everyone to enjoy.

📍 Google Maps | Phone: (312) 637-3888 | Time Out Market Website | Hours: 8 am – 10 pm Mon – Fri, 9 am – 10 pm Sat, 9 am – 9 pm Sun

Time Out Market is a food hall located in the Fulton Market District in West Loop. Here, some of the best restaurants, bars, and bakeries from around Chicago have vendor stalls all “under one roof.” Not to mention, the different selection of vendors means a wide array of cuisine options.

If you’re traveling in a group, then this is a great option to satisfy different taste buds. Everyone can order something unique but still enjoy a great meal together. No reservations are needed, but depending on what time you eat here, you may have to scour around for some seats.

If you’re interested, the upstairs level of the building serves as an event space with a steady lineup of guests and programs.

👉 Pro Tip: To get good seating on a busy day, have someone in your group secure some spots, and then take turns ordering.

McDonald’s Global Headquarters

A McDonald’s in the West Loop that serves up menu items from around the world.

📍 Google Maps | Phone: (312) 291-9224 | Website | Hours: 6 am – 10 pm daily

I know it seems odd to list McDonald’s among top Chicago attractions, but hear me out. “Global McDonald’s,” as most people call it, has a bonus international menu. This “Global Favorites” menu includes McDonald’s items around the world.

The menu isn’t extensive, but it’s a fun way to try something different. For example, you can try sweet potato fries from the Netherlands or an ebi filet-O from Japan. Find this McDonald’s global headquarters restaurant in the West Loop neighborhood.

Starbucks Reserve Roastery

Enjoy specialty drinks and food at the largest Starbucks in the world.

a display case filled with different types of food

the inside of a building with a lot of windows

📍 Google Maps | Phone: (312) 283-7100 | Hours: 8 am – 8 pm Mon – Thu, 8 am – 9:30 pm Fri – Sun

The Starbucks Reserve Roastery in Chicago is the largest Starbucks in the world! It’s located on Michigan Avenue along the Magnificent Mile.

There are five floors to this Starbucks Reserve. You’ll find a gift shop, a coffee bean scooping station, a bakery & cafe, an experimental coffee bar, a cocktail bar, and a rooftop terrace.

I mostly recommend visiting to try something different, like the pastries, savory dishes, or cocktails. Just be prepared to potentially wait in a long line, as visiting this Starbucks Reserve is a bit touristy.

The Violet Hour

This speakeasy-type bar with unique and creative cocktails is nestled in the heart of Wicker Park.

📍 Google Maps | Phone: (773) 252-1500 | Website | Hours: 5 pm – 12 am daily

The Violet Hour is one of Chicago’s best speakeasy bars. It’s located in the heart of Wicker Park and is “hidden” behind a mural wall.

The Violet Hour has a moody and intimate atmosphere, which makes it a great spot for a date night or catching up with close friends. The menu has an awesome selection of craft cocktails with unique flavor combinations. Be sure to check out the seasonal menu, too.

The drinks at Violet Hour are always tasty and the bartenders are knowledgeable and friendly. You can grab some small bites here as well.

Cindy’s Rooftop

This trendy rooftop bar that overlooks Grant Park offers sprawling city views.

📍 Google Maps | Phone: (312) 792-3502 | Website | Hours: 11 am – 11 pm Mon – Thu, 11 am – 12 am Fri, 10 am – 12 am Sat, 10 am – 11 pm Sun

Cindy’s Rooftop is an awesome Chicago bar for its rooftop views alone. It’s located on the 13th floor of the Chicago Athletic Association, which is a beautiful boutique hotel in the Loop. Cindy’s Rooftop directly overlooks Grant Park, giving you stunning views of the park, downtown Chicago, and Lake Michigan.

You can order craft cocktails, classic drinks, and full meals at Cindy’s. The offerings are good, but just know that they’re pricey. This place always books up, so be sure to make reservations in advance, if possible. Although, it does accept walk-ins. Overall, Cindy’s is an amazing spot for a date night or a special occasion.

Hidden Gems

Myopic Books

One of Chicago’s largest used bookstores in the heart of Wicker Park.

📍 Google Maps | Phone: (773) 862-4882 | Website | Hours: 12 pm – 8 pm daily | Entrance: Free

Myopic Books is one of Chicago’s largest used bookstores. It’s located in the heart of Wicker Park and is the perfect place to wander if you’re a book lover.

You’ll find three floors packed with floor-to-ceiling shelves of used books. Genres range from coffee table art books to classic novels and everything in between.

The cozy but buzzing ambiance is what makes Myopic such a cool bookstore to visit. It’s a great spot to come with friends, alone, or even on a date.

Poetry Foundation

A peaceful library and cultural center in River North that’s solely dedicated to poetry.

📍 Google Maps | Phone: (312) 787-7070 | Website | Hours: 11 am – 5 pm Wed & Sat, 11 am – 7 pm Thu, 9 am – 5 pm Fri, Closed Sun – Tue | Entrance: Free

The Poetry Foundation is a poetry library and cultural center in River North. This hidden gem is for anyone who loves poetry, books, or anything literary. The best part? It’s totally free to visit.

The library at the Poetry Foundation contains over 30,000 volumes of poetry and the shelves are packed from the floor to the ceiling. The atmosphere here is serene and quiet, so it’s the perfect place to read or write. The Poetry Foundation is one of my favorite spots in downtown Chicago.

Promontory Point

Relax and picnic at this small and scenic Lake Michigan outcrop near Hyde Park.

📍 Google Maps | Phone: (312) 742-5369 | Website | Hours: 6 am – 11 pm daily | Entrance: Free

Promontory Point is a small park well-loved by locals who know about it. This outcrop of green space is located near Hyde Park on Chicago’s South Side.

The park juts out onto Lake Michigan and provides beautiful distant views of the Chicago skyline. There are bonfire pits for barbecuing and plenty of grass to spread out and enjoy a picnic with friends or family. Promontory Point is also nice for setting up a hammock or just taking a peaceful stroll by the water, since it connects with the Lakefront Trail.

Chicago River Dinner Cruise

Dine along the Chicago River and enjoy a romantic meal as the cityscape passes by.

📍 Google Maps | Website | Tickets: $174 adults | 👉 Premier Chicago River Dinner Cruise

A Chicago River dinner cruise floats you through the heart of the city while you enjoy a plated 3-course meal. Dinner lasts about 3 hours and is typically accompanied by live music or a DJ.

The best part of a Chicago dinner cruise is the ambiance. The city skyline towers above guests in cocktail attire and evening lights glisten on the water. It’s a great idea for romantic date nights or celebrating special occasions.

Winter Garden at Harold Washington Library Center

A quiet winter “garden” and sitting area on the top floor of a massive downtown library.

📍 Google Maps | Phone: (312) 747-4300 | Website | Hours: 9 am – 8 pm Mon – Thu, 9 am – 5 pm Fri & Sat, Closed Sun

Chicago’s Harold Washington Library Center is one of the largest public libraries in the world. The building itself takes up an entire city block! It’s hard to miss with its unique Postmodern architecture. The brick structure is capped with a green-hued steel cornice. Intricate sculptures appear on each corner, featuring owls which represent wisdom.

The Winter Garden appears on the 9th floor. Its atmosphere is quiet and peaceful, so it’s perfect for reading a book or doing a little work on a rainy day. There’s also a small museum you can walk through, which is all about the history and legacy of Chicago’s first African-American mayor, Harold Washington.

Graceland Cemetery

Many notable Chicagoans are buried at this large, historic, and beautiful cemetery in Uptown Chicago.

📍 Google Maps | Phone: (773) 525-1105 | Website | Hours: 8 am – 6 pm Mon – Fri, 9 am – 4 pm Sat & Sun | Entrance: Free

Graceland Cemetery isn’t on most Chicago tourists’ lists, but it’s a unique and peaceful place worth visiting. This large cemetery is located on Chicago’s North Side in the Uptown neighborhood.

So much Chicago history lives on here, despite it being a place for those who have passed on. Prominent Chicagoans from government, sports, architecture, philanthropy, and so many other areas of life are buried here.

The cemetery’s landscape and architecturally unique monuments and mausoleums are another thing that makes Graceland Cemetery beautiful. Stop in the Graceland Cemetery office to grab a map and take a self-guided tour.

AIRE Ancient Baths Chicago

Find a little zen in bustling Chicago at this intimate, luxury spa that offers bath treatments and massages.

📍 Google Maps | Phone: (312) 312-9610 | Website | Hours: 8 am – 10 pm daily | Cost: $200+

AIRE Ancient Baths is a luxurious spa in Chicago’s River West area. This spa isn’t your ordinary one. Instead, it’s housed in a restored factory and designed to feel like an ancient traditional bathhouse.

This spa is luxurious and best known for its many pools, which include thermal baths and pools of different temperatures. You can also book massages and spa experiences for couples. Just note that the prices match the luxurious services. Booking a spa experience at AIRE is ideal for special occasions.

Chicago Entertainment & Nightlife

The Second City

Laugh your heart out at one of Chicago’s best comedy clubs.

📍 Google Maps | Phone: (312) 337-3992 | Second City Website | Hours: Showtimes vary | Entrance: $25+

Second City comedy club in Old Town, Chicago has a long history and influence that’s made waves throughout the comedy world. Famous comedians like Joan Rivers, Bill Murray, Mike Meyers, Tina Fey, Amy Poehler, and so many others have performed and debuted here.

If you’re someone who enjoys going out to shows (and frankly, just having a good time), snag a ticket to Second City. Shows can range from sketches and improv to stand-up and open mic nights.

A kitchen and bar is also available at the venue. A comedy show at Second City is sure to be a memorable experience. After all, they say laughter is the best medicine.

👉 Pro Tip: The Second City does have an age requirement. Only those 13+ will be admitted, although ages 13-17 will need adult accompaniment.

Chicago Theatre District

Witness world-class theatre and music concerts in downtown Chicago.

📍 Google Maps | Theatre District Website | Hours: Showtimes vary | Entrance: $25+

In the northern part of the Loop is the Chicago Theatre District. Here, you’ll find a wide array of theatres and performance venues. One of the major ones? The Chicago Theatre. This theatre, which primarily serves as a music and comedy venue, is widely known for its iconic red and gold marquee sign.

A few other big theatres in the district include CIBC Theatre, James M. Nederlander Theatre, and Cadillac Palace Theatre. Each of these venues offers exciting Broadway and non-Broadway productions. Either way, Chicago holds its own when it comes to a flourishing theatrical scene.

👉 Looking for shows? For a more comprehensive list of theatres and independent venues, check out the website link above.

Joffrey Ballet at Lyric Opera House

Get dressed up and treat yourself to an evening of ballet at a beautiful and historic opera house theater.

a woman standing on top of a stage holding a kite

a large auditorium filled with people sitting in chairs

📍 Google Maps | Website | Hours: Showtimes Vary | Tickets: $36-$200

Treat yourself to a fancy night out by nabbing tickets to see the Joffrey Ballet perform at the Lyric Opera House. The Joffrey Ballet is one of the most renowned ballet companies in the country. They perform a mix of contemporary and classical repertoire. As someone with a ballet background, I can assure you they’re worth seeing.

They perform at the Lyric Opera House in the Loop, which is a historic Art Nouveau and Art Deco-style theater. The architecture is stunning from the lobby to the theater itself, featuring opulent red and gold detailing.

Make a night out of seeing the Joffrey Ballet by making reservations at a nice restaurant in the Loop or River North. Head to the ballet right after!

Buddy Guy’s Legends

Step into the heart of Chicago blues.

📍 Google Maps | Phone: (312) 427-1190 | Buddy Guy’s Legends Website | Hours: 5 pm – 1 am Fri – Sun & Wed, Closed Mon, Tue & Thu | Entrance: $15+ each show may vary

If you’re a fan of classic American blues, then visiting Buddy Guy’s famous Legends Blues Club is a must. Since its opening by Buddy Guy in the summer of 1989, this music venue has become a Chicago music institution and is one of the world’s premier blues clubs.

The Legends’ stage has been played by iconic musicians like the Rolling Stones, Eric Clapton, David Bowie, John Mayer, and more. If you’re at all interested in music and Chicago’s music history, then attending a show here is sure to be a Chicago highlight.

Who knows, you might be lucky and get a surprise performance from Buddy Guy.

Symphony Center

Listen to one of the best orchestras in the world.

📍 Google Maps | Phone: (312) 294-3000 | Chicago Symphony Orchestra Website | Hours: Showtimes vary | Entrance: Ranging from $30 – $300

The Symphony Center is located in the heart of the Loop and is a great itinerary addition if you’re a classical music lover.

The Chicago Symphony Orchestra, which is world-renowned, performs here throughout the year in a range of styles. You can expect classical performances as well as contemporary ones.

The Symphony Center also offers music series to engage younger audiences. Kid-friendly programs are available as well as movie-inspired musical performances. In addition, the Symphony Center welcomes pianists, jazz artists, and performers of world and folk music.

FAQs About What to Do in Chicago

What is the number 1 attraction in Chicago?

Millennium Park, which houses Cloud Gate, is consistently ranked as one of the top attractions in Chicago. Although Millennium Park is worth visiting, there are a ton of other things to do and ways to explore the city.

Is Chicago worth visiting?

Chicago is worth visiting as it offers a wide variety of activities and attractions to choose from. The people are friendly, the city, parks, and lake create a unique experience, and there is always something to do.

What is Chicago famous for?

Chicago is famous for sports, music, the food scene (including deep-dish pizza), architecture, and so much more.

What are some free things to do in Chicago?

Millennium Park, the Lincoln Park Zoo, the Lakefront Trail, and the Chicago Cultural Center are great free activities to consider. For more, see our full list of free things to do in Chicago.

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Now you know what to do in Chicago! The Windy City has so much to offer, and I really believe there’s something for everyone.

Next up, check out my ultimate Chicago itinerary for more trip-planning help.

about me

Welcome to my travel website! I’m Mary Howard, an American who has been exploring the world full-time for 8 years.

Together with my husband, Intan, we often find ourselves in our second home, Bali, but our adventures take us to exciting destinations all over the globe.

Join us on our journey!