One Day in Chicago (Perfectly Planned, By a Local)

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I’m a Chicago, Illinois local here to help you plan the perfect itinerary for one day in Chicago. 

The Windy City is the third largest city in America. It can be overwhelming to narrow down the best things to do in Chicago if you’re just visiting for one day. This guide takes out the guesswork. 

I’ve created the ultimate one-day Chicago itinerary that will show you Chicago’s major attractions — and a couple of personal favorites! This guide is organized geographically so you won’t waste any time. Plus, it provides alternate plans for unexpected weather, varying interests, and all budgets. 

👉 Want to extend your trip? Check out our perfectly planned 5-day Chicago itinerary. You can get a free, printable version of the itinerary here.

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One Day Chicago Itinerary

8 AM – Breakfast and 360 Observation Deck at 875 North Michigan Avenue

Begin your morning in Streeterville, a vibrant neighborhood in downtown Chicago. Fill up on a hearty breakfast at Wildberry Pancakes and Cafe (196 E Pearson St) or Cafecito (215 E Chestnut St). 

After breakfast, you’ll walk a block over to 875 North Michigan Avenue (formerly John Hancock Center). Here, you’ll ascend to the 94th floor to reach the 360 Observation Deck. I recommend booking general admission tickets online ahead of time and reserving the 9 am or 9:30 am time slots to stay on schedule with this itinerary. 

You’ll find yourself towering above the city at the 360 Observation Deck, with skyline views of downtown Chicago and Lake Michigan all around. The floor-to-ceiling windows make this the perfect place to snap pictures and get a feel for Chicago from up above. 

You’ll have the option to take a ride on TILT while you’re at the observation deck. TILT is known as “Chicago’s highest thrill ride” and is an experience that tilts you 1,000 feet over the Magnificent Mile. This is a unique sightseeing experience that’s perfect for thrill seekers. I wouldn’t recommend TILT to those afraid of heights. 

10:30 AM – Walk Down the Magnificent Mile

Take a stroll down the Magnificent Mile once you’re done at the 360 Chicago Observation Deck. All you’ll need to do is exit the former John Hancock Center and walk south along North Michigan Avenue.  

Spend the next hour and a half wandering name-brand shops along this famous shopping street. You’ll find everything from luxury stores like Gucci and Cartier to trendy stores like Zara and H&M. Families with children might consider visiting American Girl Place and the LEGO Store.

The Starbucks Reserve Roastery is also on the Magnificent Mile. It’s the largest Starbucks in the world and a good spot to hit up if you want a coffee or snack to hold you over until lunch. Just be mindful that lines can be long so waiting might not be worth it since this itinerary is packed.

Be sure to look up every now and then while you stroll down North Michigan Avenue. There are tons of iconic Chicago landmarks to spot. These include the Historic Water Tower, Tribune Tower, and Wrigley Building. 

Noon – Lunch and Sightseeing Along the Chicago River

The afternoon is going to be taken up by more Chicago sightseeing and a tasty lunch. There are two options to choose from, depending on how much planning time you have for this one day in Chicago.

Option 1: Architecture River Cruise and Pizzeria Portofino

The first option is for those who have time to plan.Book an architecture cruise along the Chicago River for noon. River tours are a fantastic activity for first-time visitors and I personally recommend architecture cruises to my friends and family. 

The meeting point for this architecture river cruise is at the end of North Michigan Avenue, perfectly wrapping up the previous part of this itinerary. 

You’ll board the boat and be taken along the river while a tour guide narrates facts about Chicago. The boat tour also explains the Great Chicago Fire and points out important landmarks.

After the river tour, walk a few blocks along the Chicago Riverwalk to Pizzeria Portofino for lunch. Be sure to make reservations and ask for patio seating if possible.

Option 2: The Chicago Riverwalk and Revival Food Hall

The second option is for those with less time. Take a walk along the Chicago Riverwalk once you’re finished with the Magnificent Mile. Enter at the southwestern corner of DuSable Bridge. Spend the next hour or so wandering the Riverwalk and admiring the sights. 

Look out for buildings like the Marina Towers (locally known as the “corn cobs”) and the Merchandise Mart. The Riverwalk is also a great spot to sit and people-watch.

Head over to Revival Food Hall when you’re ready for lunch. It’s six blocks south of the Chicago Riverwalk in the Loop. Here, you can choose from several local food vendors. 

2:30 PM – Cloud Gate, Millennium Park, and Art Institute of Chicago

Walk on over to Millennium Park after lunch. This is where you’ll see the most iconic Chicago landmark: Cloud Gate (better known as “The Bean”).

Snap some photos at this famous mirrored sculpture and take a quick look around Millennium Park. Spots like Crown Fountain and Lurie Garden (my favorite spot) are worth checking out. 

Walk a few minutes south past Millennium Park through Grant Park to reach the Art Institute of Chicago. Spend the next couple of hours perusing Impressionist and Renaissance artwork, sculptures, historic artifacts, and contemporary art installations. Keep an eye on the clock, though, as the Art Institute closes at 5 pm most days.

👉 Alternate Plans: Swap out the Art Institute of Chicago with the Chicago Cultural Center if you visit on a Tuesday or Wednesday when the Art Institute is closed. The Chicago Cultural Center is close by and free.

5:30 PM – Dinner and Dessert in the West Loop 

Make your way to Chicago’s West Loop neighborhood for dinner and dessert. You can take the Pink Line train headed towards 54th/Cermak from the Adams/Wabash stop and ride to the Morgan stop. You can also Uber or Lyft if that’s easier for you.

Dinner is going to be at Time Out Market, a popular Chicago food hall complete with a bar. Time Out Market is perfect for groups, last-minute dining, and getting a taste of multiple Chicago restaurants all under one roof. 

The market space at Time Out is massive, so I recommend taking a loop around to get a feel for all the different food vendors. My favorite vendors are urbanbelly, Avli, and Arami.

Once you have your food, I recommend taking your tray(s) up to the rooftop patio on the third floor. You’ll be greeted by city views and it’s a nice spot to watch the sun go down over dinner.  

Take a quick stroll around the West Loop’s Fulton Market District after dinner. Walk over to Jeni’s Splendid Ice Cream or Levain Bakery if you want a sweet treat. Neither of these dessert spots is local to Chicago, but they’re open late and always tasty. 

8 PM – ART on THE MART or Nightlife in the West Loop 

There are a couple of options to wrap up your day in Chicago if you still have the energy. The first is a more laid-back option and the second is for those interested in nightlife. 

Option 1: ART on THE MART

Take an Uber or Lyft over to ART on THE MART, an enormous digital art display that takes place almost year-round on the Chicago Riverwalk.

Here, you can sit, grab a drink, and relax as a moving digital display is projected onto the facade of the Merchandise Mart. It’s free ( budget-friendly!) to see and it’s a fun way to wrap up the perfect day in Chicago.

River Hotel,Pendry Chicago, and Hampton Inn Chicago Downtown are all within short walking distance from ART on THE MART. These hotels are great choices if this evening option interests you. 

👉 Pro Tip: ART on THE MART has different start times throughout the year. Check the website to see up-to-date information. 

Option 2: Nightlife in the West Loop 

Stick around the West Loop neighborhood if nightlife is more your speed. There are a bunch of trendy bars here. I recommend staying around the Fulton Market District area. Lone Wolf,Blind Barber, and Emporium Arcade Bar all offer something different. 

Take an Uber or Lyft up to the River North neighborhood if you want to keep the party going, but otherwise, that’s it for this one-day Chicago itinerary!

Where to Stay in Chicago

Best Hotels 

Staying in the downtown Loop and nearby areas of River North and Streeterville makes the most sense for a brief stay in Chicago. Here are some of the top places to stay in Chicagofor different budgets and needs:

• 💵 Budget – Hi Chicago Hostel
• 🛏️ Mid-Range – River Hotel
• 💎 Luxury – Pendry Chicago
• 👪 Family-Friendly – Hampton Inn Chicago Downtown

Best Neighborhoods & Areas

Chicago has some seriously great neighborhoodsworth exploring if you have the time. These neighborhoods are the most popular for visitors:

• The Loop ( ) – The city center of Chicago. The Loop is home to major attractions like “The Bean,” Millennium Park, the Art Institute, and more.
• River North ( Search apartments in River North) – River North is just north of the Loop above the Chicago River. Trendy restaurants, art galleries, and bars can all be found here.
• Lincoln Park ( Search apartments in Lincoln Park) – A family-friendly neighborhood with charming tree-lined streets, shops, and restaurants. Lincoln Park itself, managed by the Chicago Park District, is home to free attractions like Lincoln Park Zoo.
• West Loop ( Search apartments in West Loop) – A trendy neighborhood west of the Loop. The West Loop is Chicago’s foodie mecca.
• Wicker Park ( Search apartments in Wicker Park) – An artsy neighborhood northwest of downtown. Wicker Park is full of vintage shops, coffee shops,music venues, and more.

How to Get Around in Chicago

Public transportation (trains and buses) as well as rideshares like Uber and Lyft are the best ways to get around if you visit Chicago for one day. It’s too much hassle to drive in Chicago and worry about parking if you’re just in the city briefly. 

It’s easiest to purchase a 1-Day CTA pass at any train stop. You can also purchase a CTA pass at Midway or O’Hare airports. These passes are $5 and are good for 24 hours once you first use them. You can use your CTA pass for trains and buses. 

I recommend sticking to public transportation for the most part since it’s affordable and relatively easy to navigate. However, Uber and Lyft are widely available if you want ease and convenience. 

Planning Tips for 1 Day in Chicago

Tip #1 – Stay Near the Loop 

The downtown Chicago Loop is the best place to stay for one or two nights in Chicago. Staying in the Loop or nearby neighborhoods of River North or Streeterville will ensure you’re close to the main attractions. 

Tip #2 – Visit Museums if it’s Raining

Feel free to swap out sections of this itinerary with Chicago museums if it’s raining. I recommend swapping the Magnificent Mile (10:30 am) with the Museum of Contemporary Art and sightseeing along the Chicago River (noon) with a visit to the Art Institute of Chicago or Museum Campus. These swaps should ensure you stay on schedule with this itinerary. 

Tip #3 – Wear Good Walking Shoes

This itinerary is organized to be mostly walkable, except for going to the West Loop and back to your Chicago hotel. Comfortable walking shoes should be at the top of your Chicago packing list.

Tip #4 – Swap Out Activities as You See Fit

Families and other types of travelers might want to prioritize different activities. Feel free to tailor this Chicago itinerary to your needs. Families will love attractions like Maggie Daley Park, the Chicago Children’s Museum at Navy Pier, and the Shedd Aquarium.

Other notable attractions include Grant Park (which encompasses the smaller Millennium Park) and the Willis Tower (formerly Sears Tower). It’s the tallest building in Chicago and offers spectacular views from its Skydeck on the 103rd floor. 

Tip #5 – Don’t Feel Pressured to Only Do Touristy Things

A lot of Chicago’s tourist activities are fun, especially when you visit Chicago for the first time. But don’t feel pressured to eat deep-dish pizza, a Chicago-style hot dog, and other similar tourist things. Read our 5-day Chicago itinerary for more ideas on local activities day-by-day. 

Tip #6 – Be Mindful of Events and Holidays

Chicago hosts a lot of awesome festivals and events all year long. Be mindful of major Chicago festivals that may affect this itinerary. Examples include Lollapalooza and the Chicago Blues Festival. 

FAQs About One Day in Chicago Itinerary

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I hope you enjoyed this Chicago itinerary! This Chicago itinerary is jam-packed, but it’s meant to show you the highlights of the Windy City in a hassle-free way. Check out our list of top Chicago travel tips for more helpful information.