What's the best time to visit Chicago?
The best time to visit Chicago is during summer (June-August) with pleasant weather for outdoor activities, rooftop dining, and beach visits. Enjoy fireworks at Navy Pier, boat tours, and summer festivals like Do Division Street Fest in June, Square Roots Festival and Windy City Smokeout in July, and Lollapalooza and Chicago in Tune in August. Book accommodations early due to high summer tourist demand.
If you’ve ever wanted to find out the best time to visit Chicago, what museums to visit, where to party at night, and what festivals you should keep an eye out for, this is the travel guide that has all the answers you need.
We’ll also cover the cheapest time to head to Chicago, how to steer away from the crowds, and when to avoid visiting. But first, let’s explore why visiting Chicago is worth your time to begin with.
The Overall Best Time to Visit Chicago
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The overall best time to visit Chicago is in summer (June—August). It’s the busiest season for the city, when the weather is at its finest — temperatures are between 57°F and 84°F, so outdoor events are in full swing and beachgoing is at its peak.
The season is ideal for eating out or drinking on some of the city’s rooftops and patios, enjoying the free fireworks twice per week at Navy Pier, and exploring the city by embarking on a boat tour.
The summer festivals are a must, too — in June, there’s the Do Division Street Fest, promising live music, food vendors, and fun for the whole family each year; and the yearly Chicago Pride Parade.
July has the Square Roots Festival, a cool music and craft beer street fest, and Windy City Smokeout, a BBQ and country music festival that offers live country music, beer, and ribs.
In August, the city hosts the world-famous Lollapalooza, a yearly four-day music festival, and Chicago in Tune, a citywide festival honoring Chicago’s versatile music scene.
The days can be quite hot and humid at times, but it’s nothing water recreation and festival going can’t make better. Also, as this is the most popular time of the year to visit Chicago, booking your stay in advance is mandatory.
Cheapest Time to Visit Chicago
Chicago, IL, USA – October 22nd 2021: View of an impressive fossil skeleton of a Titanosaur, one of the largest animals ever lived, at the Field Natural History Museum in Chicago, IL, USA/schusterbauer.com/Shutterstock
The cheapest time to visit Chicago is in the fall (September—November). Airfare prices are more affordable, accommodation rates are reduced, and fall is generally considered to be the least expensive period to pay Chicago a visit.
The weather is still more or less pleasant — the temperatures vary between 32°F and 75°F. In early fall, you can even do almost every activity you’d do in summer in Chicago, just without the peak season tourists and through-the-roof prices.
The only thing to keep in mind is that certain attractions may have already reduced work hours, such as the Lincoln Park Zoo and the Navy Pier.
Popular fall events in September include Taste of Chicago; the world’s largest food festival held in Grant Park, Chicago Gourmet; Riot Fest, a yearly three-day punk rock music festival; Oktoberfest, where you can enjoy different beers and try authentic German food; Pitchfork Music Festival, an annual summer music festival organized in Union Park, and Hyde Park Jazz Festival, a yearly coming-together of jazz lovers.
In October the city hosts the popular Chicago International Film Festival; the Bank of America Chicago Marathon for travelers who wish to add more dynamics to their Chicago stay, and Chicago Beer Fest, offering a wide selection of breweries.
One of the most popular events in the entire year, The Magnificent Mile Lights Festival (November), is an annual event taking place the Saturday before Thanksgiving, where one million lights brighten Michigan Avenue on 200 trees.
Least Busy Time to Visit Chicago
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The least busy time to pay Chicago a visit is in spring (March—May). Spring is ideal for travelers who want to take advantage of the lack of crowds to explore Chicago in a laid-back way, as the temperatures are much milder than in winter — they typically range between 28°F and 70°F.
While it rains occasionally, this shouldn’t cause any major disruptions to your journey.
In terms of popular events around this time, mark your calendar for the following ones: St. Patrick’s Day Parade (March), when you can witness the Chicago River being dyed green; Chicago Restaurant Week (March-April), honoring the city’s culinary scene; Chicago Latino Film Festival (April), the longest running Latino film festival in the US; and Chicagoland Spring Marathon & Half Marathon (May), where you can either test your limits or cheer on other runners.
Worst Time to Visit Chicago
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The worst time to visit Chicago is in winter (December—March). Chicago winters are infamous for being cold — expect below-freezing temperatures between 12°F and 36°F, and snow.
While certain winters are milder, the bottom line is that Chicago is much more pleasant in other periods of the year. Snowstorms aren’t that frequent, but make sure to always check the weather forecast and follow local advice if you’re there in winter.
Canceled flights or blocked roads aren’t unheard of and may impact your itinerary. Also, rivers are lakes may freeze, which translates into canceled cruises.
However, if visiting Chicago in winter is your only option, take the time to explore its museums, theaters, and comedy clubs.
Those ready to embrace Chicago’s winter conditions should keep an eye out for some popular outdoor events such as Christkindlmarket Chicago, a unique traditional market providing visitors with shopping fun, family-friendly events, and intercultural activities.
Other popular events around this time include Winter WonderFest (December-January), the city’s biggest indoor winter playground; the Garfield Park Conservatory Spring Flower Show (beginning in February), ideal for those looking to enjoy freshly blossomed flowers, and the Chicago Auto Show (February).
Book Your Trip to Chicago Today!
| 👍 Best Time to Visit | June to August |
| 💲 Cheapest Time to Visit | September to November |
| 🗓️ Least Busy Time to Visit | March to May |
| 👎 Worst Time to Visit | December to March |
So, with so much to see and do, what are you waiting for — book your trip today and experience for yourself all that Chicago has to offer. Happy travels!