When is the Best Time to Travel to Chicago

The Second City, rebuilt after the devastating Great Chicago Fire of 1871, is a Midwestern marvel. This glistening city along Lake Michigan is my favorite city in the world, so I made it my home. While the peak tourist season in Chicago is the summertime because people are averse to cold weather, this is truly a place worth seeing at any time of year. 

Despite its moniker of the Windy City, Chicago isn’t much more windy than any other city. Downtown has its wind tunnels from the towering buildings, but the name actually derives from politicians in the city being full of hot air. Thanks to those windbags, we got stuck with an unflattering nickname. 

But it’s good news for you adventurers! Because it means you don’t have to worry as much about being blown away by anything other than this magnificent city’s sights, tastes, and vibrancy. So whether you’re a cold weather aficionado like me or prefer the scorching summer sun, Chicago’s seasons have all that and more. 

Spring (March to May):

Although Chicago is no stranger to a random April snow shower, springtime is a fabulous time to visit the city. Like the tulip displays along the Magnificent Mile, Chicago returns to life. Spring is a shoulder season in Chicago, so things like hotels will be cheaper than in the summer. 

Each March brings about events like the Chicago Flower & Garden Show or dyeing the Chicago River green for St. Patrick’s Day. Highs during the spring typically range from the mid-40s to the mid-60s (Fahrenheit) = 4 to 15 (Celsius). 

Summer (June to August):

Spring in Chicago is like the opening act to the headliner, which is a Chicago summer. Festivals abound during the summer months, bringing something new and exciting practically every week. Because this is the peak of Chicago tourist season, you will have higher prices than during other seasons. 

For things like the Millennium Park Music Series and Lollapalooza, you will have to contend with high-humidity summer days. Average temperatures range from the upper 70s to the 80s (Fahrenheit) = 21 to 26 (Celsius), though our humidity often makes it feel hotter. 

• Chicago Pride Fest (June)
• Chicago Blues Festival (June)
• Grant Park Music Festival (June-August)
• Pitchfork Music Festival (July)
• Wicker Park Fest (July)
• Taste of Greektown (August)
• The Great American Lobster Fest (August)

Here is a list with links to all the festivals throughout the year.

Fall (September to November):

Even while the heat of summer starts to die away, Chicago’s color remains. We trade brilliant floral displays for fall foliage – a trade I’ll happily make. Tree canopies line many of the streets of our neighborhoods, bringing a whole new look to them as the temps simmer down.

As autumn and leaves descend, fewer tourists take to the streets. You get a slightly less crowded version of Chicago without sacrificing any of the excitement. Expect high temperatures ranging from the mid-70s down to the 50s (Fahrenheit) = 10 to 21 (Celsius). If you’re in the Midwest in the fall, you may need to wear a t-shirt in the morning but have a cardigan by the evening. 

• Taste of Chicago (September)
• Chicago Jazz Festival (September)
• Riot Fest (September)
• Chicago International Film Festival (October)
• Chicago International Latino Theater Festival (October-November)
• Christkindlmarket Chicago (November-December)
• ZooLights at Lincoln Park Zoo (November-December)

Winter (December to February):

Winter isn’t usually someone’s favorite time of year in Chicago – unless they’re me. Despite the sometimes chilly temps, Chicago in the wintertime is a magical place. Particularly ahead of the winter holidays, the city’s glow grows ever brighter with holiday lights shimmering against the freshly fallen snow. 

These are the cheapest months to visit the city, with the exception of holiday weekends. Only some tourists want to venture out when the temperatures drop. Even though there are far fewer outside activities to do, ice skating in Millennium Park or wandering the Lincoln Park Zoo looking at Christmas lights makes any cold bearable. Temps will range from highs in the 40s to the 30s (Fahrenheit) = -1 to 4 (Celsius). 

• Winter Flower Show at Garfield Park Conservatory (November-January)
• Fillet of Solo Festival (January)
• Chicago Restaurant Week (January-February) 
• Chicago Theatre Week (February)
• UChicago Folk Festival (February)

Travel Tips

• Budgeting: No matter when you visit Chicago, investing in a CityPass is always a good idea if you’re planning on hitting the big stops. If you’re a museum person in particular, it is much cheaper to get a CityPass than book things like Shedd Aquarium, The Field Museum, and the Museum of Science and Industry individually. 
• The Weather: Understand that Midwestern weather is unpredictable. You could show up and have 70-degree weather in February and freezing temperatures in May. Even being a lifelong Midwesterner, sometimes the weather changes take me by surprise. 
• Car Rentals: If you aren’t used to winter weather and you’re visiting in the winter, please don’t get a rental car. Driving in snow and ice takes practice. It isn’t worth the risk for your safety and that of other drivers. 
• Public Transportation Safety: Chicago has a generally good public transportation system. It has bumps, but overall, our buses and trains do the job. That said, you’ll be in a big city. Big cities have crime. Just be aware of your surroundings at all times, particularly on public transit, and you should be fine.
• Safety: Do not keep your wallets and cell phones in your back pockets, and be aware of where your bags are at all times. And never ride in an empty train car by yourself if you can avoid it. 

Conclusion

Determining what time of year to visit Chicago depends on what you want from the trip. If outdoor festivals are the least of your concerns, consider the cheaper and chillier winter months. For folks who want to be inside anyway at our fabulous museums, theaters, and art galleries, it makes sense to take advantage of the savings. But for anyone hankering for the festival scene, a Chicago summer clearly wins out above the rest. 

Part of Chicago’s Midwestern charm is that it has distinct seasons. Though we often joke that Chicago only has two seasons, summer and winter, we do have more variety than some of the other metros in the country. Complete with swimmable beaches (shark-free), public art galore, more shopping than you could imagine, and some of the finest restaurants in the country, Chicago is a smorgasbord waiting to be explored.