The Best Time to Visit Chicago

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• My favorite locations to lodge in Chicago
• My selected lodgings in Chicago
• My favorite family-friendly hotels in Chicago

In my assessment, the best timeframe of the year to visit Chicago is in June or September, when you’ll find fewer crowds than in summer and preferable weather than in winter. Rates on hotels and flights won’t be the most cost effective during this period, but they’ll be somewhat more affordable than during the summertime rush. Autumn offers the clearest weather.

When is the best time to go to Chicago?

• Optimal Time to Visit Chicago for Pleasant Climate:
  Chicago encounters the complete scope of climate, with blustery winters and sweltering summers. The finest times to pay a visit for more moderate weather is in late Spring, early summer, and early fall; specifically May, June, September, and October. Temperatures are usually mild during these months, with averages between 12°C and 21°C. May and June can be a little rainy, so bring an umbrella, just in case. September and October have generally clear skies.
• The best time to visit Chicago for budget-friendly rates is:

For Chicago, the best time for getting good deals on flights, rooms, food, and entertainment is in winter, especially in January and February. Hotel room occupancy is at its lowest during these months, hovering around 50%, so even luxury hotels offer deep discounts. Late November and early December also see dips in pricing for hotels. Chicago Restaurant Week begins in late January and Theater Week is in February, making this an ideal time for savings across the board. Be advised that Chicago winters are incredibly cold, averaging -6°C in January, and often snowy, so do bundle up if you plan on braving the city.

• Optimum Duration for Enjoyment When Visiting Chicago With Kids and Family:
  Summer, specifically from June through September, tends to be an incredibly well-liked timeframe for families to journey to Chicago. The days last the longest during this period, the water is perfect for swimming, and there is no shortage of kid-friendly happenings scheduled. Nonetheless, summer can also bring intensely hot weather, overcrowding, and expensive family travel! When visiting in summer, planning for August may be best. Although the deals won`t match those available in winter, it is normally the most reasonably priced of the summer months and the climate tends to be cooler and drier than July. If the kids` school calendar allows, aiming for April could work well. The conditions are commonly more pleasant during this time, lodging is a touch less expensive, and family activities still abound.
• Best Time Period to Visit Chicago for Art and Museums:
  Major cultural institutions in Chicago`s world-renowned museum scene are mandated to offer complimentary entrance to all Illinois inhabitants for 52 days annually. Each facility selects different times to honor gratis admittance, while for non-residents of Illinois, free entrance is occasionally obtainable on specified occasions. For example:
  • Sundays offer free admission at the McCormick Bridgehouse, and Chicago Children’s Museum is free on first Sundays for visitors 15 and under.
  • Tuesdays offer free admission to the Loyola University Museum of Art, the International Museum of Surgical Science, and DuSable Museum.
  • Wednesdays are free at Glessner House and Clarke House, with complimentary guided visits on Wednesday, Thursday, and Friday.
  • Thursday evenings are free at Chicago Children’s Museum, from 5-8pm.
  • Numerous other museums, including the Oriental Institute,National Museum of Mexican Art, the Money Museum, and the Lincoln Park Zoo make their exhibits accessible for viewing free of charge every day throughout the entire year.
• Best Time to Visit Chicago for The Performing Arts:
  Chicago possesses one of the hottest theater scenes across the nation. Any moment is ideal for experiencing a showing, but the best time to pay a visit is during Theater Week in February, with over 100 productions taking place over ten days. Musical festivals initiate in June with Do Division (a family-friendly occasion with a widespread selection of music, plus a fashion show, family activities, and cuisine) and concluding in September with Riot Fest (punk, indie rock, and hip hop). The summer weeks in between have musical festivals for jazz, blues, Latin, and more. Chicago also possesses an amazing dance scene. Verify it out in April for Chicago Dance Month, with over 50 performances, occasions, and classes at discounted rates. From late June through early September, pay a visit for Chicago SummerDance; this free occasion has dance lessons followed by freestyle dancing every Friday through Sunday in the Spirit of Music Garden
• The best time to visit Chicago for outdoor activities is:
  Chicago is home to around 26 miles of beachfront along the Lake Michigan shores. The water is here cool and blue, making this a prime summer hangout spot from late May through early September. Local favorites include Oak Street Beach,Montrose Beach, and Rainbow Beach. The Lakefront Trail runs for 18 miles, perfect for a walking or cycling while taking in the scenery. The summer months are also prime time for river cruises and kayaking. Water is comfortable from June through September, with August being the warmest. In the colder months, Chicago is a winter wonderland, with plenty of ice skating rinks scattered around the city, generally open from late November through early March, though December through February is the ideal time for a good freeze. For great sledding, visit Soldier Field Sledding Hill, which stays lit at night (they do add fake snow occasionally). Northerly Island, where you can snowshoe or cross-country ski, is a hidden gem for winter fun.

€› Item: Best Time for Food in Chicago:
.€� Chicago has two enormous food festivals in the summer: Taste of Chicago in July (a five-day, outdoor array in the Loop) and Chicago Gourmet in September (a star-studded, fine cuisine festival in Millennium Park). Smaller neighborhood festivals occur all summer long, mainly from May through September. Chicago Restaurant Week is a two-week event of fixed-price feeds at diverse dining places citywide; it takes place from late January through early February. For Chicago’s most beloved nutritional products, try the Chicago Pizza Party in February and the Chicago Hot Dog Fest in August.

• Best Time to Visit Chicago for Structural Works:
  Chicago is known for its stunning architecture and skyline. There are many ways to take in the urban landscape, whether by boat, on foot, or from high up in an observation deck. If going by boat (the best way!), you’ll want to visit from April through November, when the Chicago Architecture Foundation is offering their acclaimed river cruises. If going on foot, you’ll want to visit between March and September, except for July, when it’s sweltering hot and very rainy. You can see the skyline all year long from inside an observation deck in Hancock Center or the Willis Tower, but you’ll still want to choose a time when the skies are clear, so choose late May through early October. Late August through mid-September is clearest.
• Preferred Time to Visit Chicago for Autumn Foliage:
  The Chicago region typically sees the first leaves changing color in September. The peak period of rich hues usually occurs around mid-October, though occasionally the brightest shades arrive by the end of that month. Areas with colorful foliage can often be viewed through November, when frost starts to take hold. Among Chicago`s extensive parks ideal for an up-close perspective on the leaves are Millennium Park and Graceland Cemetery. Alternatively, one can opt to admire the leaves from above by getting a drink at one of the rooftop bars overlooking Chicago`s green spaces, such as Cindy`s
• Best Time to Visit Chicago for Fewer Crowds:
  Winter is the least crowded time in Chicago. Hotel occupancy is at its lowest in early December, January, and February. Though the weather is cold and often snowy, this is a perfect time to travel if you’re interested in culture. Museums and restaurants will be less congested, and theater tickets will be easy to obtain.

Chicago Travel Seasons

• Summertime (June through August): Warm temperatures, sunny beaches, food and music festivals, and school holiday breaks all factor into making summer the season that is most attractive for travelers. Expect to pay high prices and deal with large crowds, but the long days are filled with an abundance of activities to do for any variety of interests. Holiday travels around late November and late December create mini spikes in travel. If traveling during any of these periods, book flights and hotels well in advance. Book the Best Chicago Hotels and the best Chicago Family Hotels far ahead of time.
• Low (November through March): The coldest time of the year in Chicago spans from November to March, excepting Thanksgiving and Christmas holidays. Airfares and lodging are quite affordable during this time, often priced around half as much as summertime rates. Those interested in the arts or cultural activities may find this a worthwhile time to visit when indoor attractions outweigh confronts with frigid weather.
• Shoulder Season (April through May and September through October) for Chicago Travel: Spring and fall make up the shoulder seasons, a transitional period between high and low seasons. You’ll find fewer crowds than in summer and better weather than in winter. Spring temps average 18°C during the day and fall to around 7°C at night. Fall temps average highs of 21°C and lows of 9°C. Rates on hotels and flights won’t be very affordable, but they will be a little more reasonable than during the summer rush. Spring tends to be a little rainy, so pack an umbrella. Fall offers the clearest weather.

Chicago Weather by Month

• Chicago Weather in January: January normally brings very cold temperatures and snow to Chicago, with average daily highs of -6°C. This month usually sees the most snowfall. More than half of the days will see snow on the ground, though it typically accumulates only around 2cm deep. About five days per month bring around 15cm of snowfall, while one or two days each month can bring over 25cm. Be sure to pack warm weather gear like waterproof boots, a thick coat, and hat for traveling in January. (Typical High -1°C, Average Precipitation 43mm, Average Snowfall 27cm.)
• Chicago Weather in February: February in Chicago continues to be quite cold in Chicago, though daytime highs tend to rise above freezing. Snow remains frequent, and nearly half the days see a thin layer of snow on the ground. Thick snow accumulation, with more than 10cm on the ground, only occurs around 5 days this month. (Average High 1°C, Average Precipitation 38mm, Average Snow 23cm.)
• Chicago Weather in March: In March, temperatures commence rising, hovering above freezing for most of the time. Weather is a blend of primarily dry days, along with some cold rain and slushy snowfall. Most of the time, you’ll want to keep your coat and boots on, but on rare occasions afternoons warm sufficiently to get away with a sweater or light jacket. Bundle back up for night, when temperatures get icy again. (Average High 8°C, Average Precipitation 67mm, Average Snow 14cm.)
• Chicago Weather in April: This month marks the initial period of the year when daytime highs reliably enter double-digit Celsius range, averaging around 15°C. Nights generally stay above freezing. April holds the title as the windiest month and tends toward wet weather. Scarves and umbrellas prove ideal accessories. While infrequent, snow can still arise, more likely in the first half. (Average High 15°C, Average Precipitation 97mm.)
• In May, Chicago enjoys one of its most attractive months, with increased hours of sunlight and warmer afternoons. However, nights tend to remain cool, so layering clothing is advised when traveling during this time period. Rainfall persists regularly, with over half the days anticipating some small showers. (Average Daytime High 21°C, Average Monthly Precipitation 88mm.)
• Chicago Weather in June: June`s dew point positions the air as neither too parched nor too damp, making it perfect. This is the initial genuinely warm month, typically seeing highs around 27°C and occasional heat surges beyond 30°C. Days are lengthening now. Though plan for rainfall; this is the second rainiest month, often bringing thunderstorms later on. (Average High 27°C, Average Precipitation 99mm.)
• As the hottest, wettest and most humid month of the year in Chicago, July brings likely chances of thunderstorms and light to moderate rain throughout the month, so planning some indoor activities is wise just in case. Days are long this time with around 12 hours of sunlight on average and highs near 29°C and precipitation averaging 100mm.
• Chicago Weather in August: August stays warm and humid most of the time, while wind speeds fall to their slowest, meaning there’s no breeze to cool things down. Thunderstorms and rain are likely this month, though less likely than in July. Water is warmest this month, making August ideal for hitting the beach or kayaking. (average high: 28°C, average precipitation: 97mm)
• Seen as one of the best times to visit Chicago, September has balmy afternoons followed by cooler evenings like June but with lower humidity levels. This is a dryer month with clear skies most days and only occasional light rain. Average highs are around 24°C and average precipitation is approximately 90mm.
• Chicago Climate in October: Autumn foliage peaks during this month. Daytime hours are shrinking and temperatures are reducing, with nights seeing thermometer readings drop back down into single digits. Rain occurs regularly at this time, but only in small bursts; this remains one of the drier months of the year. Snowfall is unusual, but not entirely unheard of. Wear layers during the day and a jacket at night. (Average High 17°C, Average Precipitation 68mm.)
• Chicago Weather in November: The month of November in Chicago is the first cooler period after summer, with evenings normally hovering around the freezing point. About half of the days are sunny and crisp, while the remainder are slightly cloudy and cool. November typically sees a scattering of snowfall events over its duration. You`ll want additional protective layers if planning an evening downtown. (Average High 9°C, Average Precipitation 67mm, Average Snow 1.2 cm.)
• Chicago Climate in December: December is actual winter in Chicago, with most days underneath 0°C on average. Snow is probable this month, though only a couple days will see over 2cm sticking. More frequently than not, the snow will dissolve into slush instead, so do wear warm, water-resistant boots when out and about. (Average High 2°C, Average Precipitation 63mm, Average Snow 22cm.)

Chicago Events and Festivals

Chicago in January

• Chicago Restaurant Week – A two-week period of prix fixe dining specials for brunch, lunch, and dinner where over 300 restaurants partake, featuring a diversity of cuisines from downtown extending out to the suburbs. Restaurant week customarily initiates in late January and continues into early February.
• Black Creativity Family Day – Hosted annually on Martin Luther King, Jr. Day by the Museum of Science and Industry, this event includes the opening of a juried art exhibit, talks with professionals in STEM fields, collaborative printmaking and more. Though the celebration itself lasts only one day, the art exhibit runs for one month, and their innovation studio runs for six weeks.
• Chicago Polar Bear Plunge – At the tail end of January, individuals from the Lakeview Polar Bear Club invite all to partake in their plunge into the lake at Oak Street Beach. Proceeds from registrants online or on site on the day of are contributed entirely to help area families in need. Swimmers can enroll at a decreased rate ahead of time or sign up when arriving.
• Stout & Chili Night – CHAOS, a homebrew club, hosts this annual occasion, pairing over 30 home-brewed stouts with a variety of chilis. A few pro brewers will add to the mix, along with music and comedy acts.
• Chicago International Puppet Theater Festival – An 11-day event featuring puppeteers from around the globe, with performances, workshops, and symposiums. Venues are scattered throughout the city, and tickets must be purchased for each individual event.

Chicago in February

• Cupid’s Undie Run – A single-mile enjoyable run on Valentine’s weekend end, with runners wearing exclusively their undergarments. The celebration starts at noon, followed by the run (therefore don’t drink excessive at the initial party!), followed by yet another celebration. Proceeds go to the Children’s Tumor Foundation and toward NF investigation.
• Hideout Makeout Party – Labeled as “an evening of auditory intimacy,” the Hideout Makeout Party is an annual musical concert including an orchestra made up of artists from neighborhood bands playing affectionate songs and film soundtracks, plus some original compositions. Anticipate covers of tunes from a range of musicians, varying from Frank Zappa to Celine Dion. The Hideout venue is a Prohibition-era bar that`s a mecca for the Chicago music scene. It lies in the northern conclusion of the city in the commercial strip between Wicker Park and Lincoln Park.
• Chicago Theater Week – A 10-day festival, featuring discounted admissions for over 100 performances throughout the city. This event demonstrates the range of the Chicago theater scene, delivering everything from plays to musicals to operas, from big budget to minimal budget shows.
• Polar Adventure Days – A complimentary event at Northerly Island, highlighting the natural surroundings of the Chicago area. Get up close with wolves, huskies, birds of prey, and more, walk on snowshoes on the island, drink hot cocoa, and make wintery crafts.

Dolphin Bay Family Beach Resort • Apollonion Palace

Chicago in March

• The Chicago Beer Festival – Hosted by the Field Museum, the Beer Festival brings jointly 70 breweries, all with their latest spring seasonal brews. Ticket price involves beer tasting, music, and access to museum exhibits. Buy a VIP ticket to get in early for unique samples poured only during this first hour. Tickets must be obtained in advance; no tickets are sold at the door.
• Holi-The Festival of Colors – Best known in the U.S. as a large celebration, where people throw vivid powders at one another, Holi is a Hindu festival that commemorates the end of winter and start of spring. This is traditionally a time to forgive and forget previous disputes, to develop friendships out of adversaries. The Vedic Cultural Society in Naperville invites everybody to join in their festival, featuring cuisine and music. The event is free of charge, but the color powder is $2 per bag; purchase it online and pick it up there or have it shipped to you beforehand. (Some years this occasion happens in February, so check the date in advance.)
• The ShamROCK GREENing – In recognition of St. Patrick’s Day, famous structures, monuments and roads across the city light up in green color. They even dye the river green! Other events include a parade, marathon and their annual ball held in various areas of the city.

Chicago in April

• Chicago Dance Month: A month-long event featuring over 50 performances and classes, many of them free or discounted. Featured gatherings vary in style, and include ballet, hip hop, tap, circus acts, and more at places scattered all around the city.
• CIMMfest – The Chicago International Films and Music Festival is a four-day celebration filled with concerts, movie screenings, and discussion panels. Films in the mornings; music at night. The event occurs at various bars, galleries, and theaters in Wicker Park and Logan Square.
• Chicago Expo of Comics and Entertainment – Also known as C2E2, this convention centered around comics and pop culture includes artists, exhibitors, screenings, panel discussions, and autograph sessions. Since 2010, this three-day event has hosted creators, celebrities, and fans of comics, video games, manga, and more. Expect many attendees in costumes, and bring cash; not all vendors here accept plastic cards.
• bluesSHOUT! – This blues dance festival lasts three days, featuring live bands, classes, acts, and competitions. Dance class skill levels are assigned by instructors after tryouts, or beginner classes are open to all

Chicago in May

• Chicago Beer Classic – This huge beerfest includes practically a hundred neighborhood and international breweries, each offering two to four beers to sample. General tickets include 48 two-ounce tastings, while VIP access gets you 60 samples, along with a tour of the place, Soldier Field, home of the Chicago Bears.
• A visit could be made to the Chicago Kids and Kites Festival – Situated on Cricket Hill in Lincoln Park, this spring event features free kites (arrive sooner to grab some before they run out!), along with pro kite demos, balloon animals, and face painting for enjoyment of family members. This popular family happening also incorporates a special kite in the afternoon that drops candy from the sky.
• Illinois Craft Beer Week – This event coincides with American Craft Beer week and features hundreds of events at venues citywide. Sample rare beers at discounted prices in landmark spaces across the city, such as the Garfield Park Conservatory. Download their smartphone app for Android or iOS for a comprehensive calendar of activities.
• Mayfest – For 3 days of fellowship, this event provides live local musical performances and diversions under a spacious canopy, along with a beer garden, delectable cuisine, and family highlights like Kids Day and a pet pageant exhibition.

Chicago in June

• Chicago Blues Festival – This event is not merely Chicago’s maximum music festival but also the biggest blues festival globally. This free occasion draws in big-name acts and a crowd of half a million. The festival takes place over 3 days with 5 stages operational, all at Millennium Park.
• Pilsen Food Truck Social – This summer festival features around 25 trucks serving various cuisines along with live music, family activities, and beer. This two-day occasion is free of charge, though a $5 donation is suggested benefiting the food trucks association and a food bank/soup kitchen.
• Dragon Boat Festival – This event occurs on the fifth date of the fifth month of the traditional lunar calendar. Its primary celebration is at Bedok Reservoir where there is a race of Dragon Boats from all over the world. This is also a wonderful time to savor traditional rice dumplings, which is why the festival is also known as ‘The Dumpling Festival’.

Chicago in July

• The Taste of Chicago festival has been a mainstay in Grant Park since 1980, attracting millions annually to sample classic Chicago fare as well as diverse world cuisines. As the largest food fair, the event also offers a wide range of live performances that have highlighted stars like Robert Plant, Jennifer Hudson, and Death Cab for Cutie over the years. Rides, games, and family entertainment options are all provided on-site.
• Rhythm World Festival – Hosted by the Chicago Human Rhythm Project, this percussion dance event includes routines, workshops, classes, and additional items spanning two days. Traditional and modern styles are incorporated.
• Square Roots Festival – This three-day event in Lincoln Square features musical performances, craft beer from local and regional breweries, tasty food, dancing, and jam sessions across genres including indie rock, world music and folk. Great free entertainment is provided with an suggested donation supporting a music school, farmers market, and concerts.

Chicago in August

• Northalsted Market Days – This is a huge two-day street fair with an LGBT focus yet open to all. It presents live music on three stages, a dance area, cuisine, arts, crafts and vendors. Several high-profile acts come through yearly; past events have seen Joan Jett and Salt-N-Pepa among others. The function is complimentary, with a proposed $10 donation, and takes place in the Boystown neighborhood.
• Oak Park Microbrew Review – A zero-waste, craft brew festival presenting live tunes and light eats. Highlighting nearly 100 neighborhood brewers, and over 200 beers, the undertaking is created by Seven Generations Ahead and is committed to having not a scrap from the festival going into a landfill. Tickets are constrained, and it has been known to sell out, so be certain to secure yours early; only a handful will be accessible at the entry.
• Chicago Jazz Festival – Occurring around Labor Day weekend, this four-day music extravaganza includes live jazz performances across various genres—either local, national or international in origin. Held free of charge at Jay Pritzker Pavilion in Millennium Park.

Chicago in September

• Chicago Gourmet – This prestigious culinary event presents cooking demonstrations, wine seminars, premium spirits and alcoholic beverages tasting, and an abundance of world-class foods. Notable highlights involve the Hamburger Hop burger contest and the Tao of Tacos competition, where skilled chefs craft novel, new taco flavors paired with beers. This occasion is restricted to those 21 years of age and older.
• Poetry River – An experiential event featuring poetry, music, dance and light, showcasing Chicago`s diversity through performances in several languages.
• Casa Horizontes Corcovado: For more secluded lodging, look into this alternative. It provides rooms, bungalows, and houses, making it one of the finest residential units in Costa Rica. Positioned half a mile from Colorada Beach, it boasts a terrace and shared garden area. .
• Fulton Market Harvest Fest – This food and drink festival includes live music and cooking demonstrations with chefs from top restaurants in the Fulton Market neighborhood and throughout the city. The $10 suggested donation for admission benefits Pilot Light, a program teaching healthier food choices to kids.
• World Music Festival Chicago – Established in 1999, this festival takes place in multiple venues across the city and has featured hundreds of bands representing over 80 countries since inception, with free admission to all concerts.

Chicago in October

• Chicago International Film Festival – This popular two-week long film event originating in 1964 has provided the breakthrough opportunity for several prominent directors, including Martin Scorsese and John Carpenter. Over half of all movie screenings feature the writers, directors, or actors from the film, who introduce the movie and remain afterwards for discussions and meetups with the audience.
• Rocktober Beerfest – A beer festival in classic German Oktoberfest fashion, Rocktober Beerfest is a three-day happening with real music and a stein hoisting competition. Expect plenty of brats, pretzels, and dudes wearing lederhosen.
• Northalsted Halloween Parade – This parade takes place in the neighborhood of Boystown in Chicago and showcases some of the most impressive Halloween costumes seen across the nation. People of all kinds are welcome to walk in the parade itself, with several competitions also arranged for costumes along with a kid-friendly scavenger hunt related to tricks or treats. Accompanying events stretch out over multiple days in the neighborhood.

Chicago in November

• Magnificent Mile Lights Festival – This event along Chicago`s Magnificent Mile, one of the largest in the country, displays holiday spirit through a parade with beloved characters, hands-on activities for families, and an impressive fireworks show over the Chicago River. Visitors can enjoy food, music, possible Santa sightings, holiday shopping along the famous street. .
• Christmas Tree Lighting Ceremony – Chicago’s Christmas Tree Lighting Ceremony has occurred in Millennium Park for over 100 years. Including live music, a visit from Santa and Mrs. Claus, and a range of iconic Christmas characters. Admission is free.

The Waldorf Hilton: A historic hotel with a rich heritage, The Waldorf Hilton offers guests a combination of classic British elegance and modern luxury. Located near Covent Garden and the West End, this hotel features beautifully-furnished rooms, a grand ballroom, and a range of dining options, ensuring a memorable stay in the heart of London.

• ZooLights – Visit the Lincoln Park Zoo (always free!) on select nights from late November through New Year’s Day to see the holiday lights and enjoy activities throughout the park. Enjoy crafts and snacks, get a photo with Santa, and watch live ice carving or a musical light show. The zoo even stays open late a few nights for special events, including a beer festival, market night, and live music.

Chicago in December

• Renegade Craft Fair – This curated craft event highlights cutting-edge, contemporary, and independent artisans of handcrafted goods plus artisanal food and drinks, and live music. It serves as a perfect destination to shop for quirky, cool gifts and perhaps something for oneself while visiting.
• Offering a party-like atmosphere with local craft beers, food truck selections and handmade arts and crafts, the Sauced Night Market – This event changes locations per occasion, so check their schedule for the latest information.
• One of a Kind Show – For four consecutive days in December, The Mart hosts around 600 vendors selling thousands of handcrafted items. Ranging from bath products to fashion to metalwork sculpture, this is a great place to find special holiday gifts, and enjoy food and entertainment while you shop.

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