Chicago is one of America’s premier tourist destinations. With world-class museums, globally influenced dining, and luxury shops galore, Chicago attracts millions of travelers each year. While most folks visit in the summer due to a combination of school vacation and the ability to take time off work, the best time to visit Chicago is actually not the middle of the summer. For most people, Chicago weather can be a real determining factor in when to visit this stellar city. It’s chilly – often bitterly cold – during the period between November and March, so most people avoid trips to Chicago in winter. On the contrary, the best times to visit Chicago are late spring/early summer, and early fall. Because travel plans can vary, however, and you may not be able to target that ideal weather in Chicago, we’ve put together a run-down of the best things to do in Chicago year ‘round, along with highlights of the best times to visit.
April – May (Best Time to Visit)
Chicago is warming up from a long, cold winter, and the weather is reliably between the high 50s and low 70s (mid-teens to low 20s Celsius). This is also a time of year when the flowers are blooming, the parks look their finest, and everyone in the city is relieved to have survived another winter. Some top things to do during this time of year include:
- Macy’s Flower Show (ends mid-April) – held in their iconic State Street location (formerly Marshall Fields), this lush display of locally grown flowers brightens up the store. Get some souvenirs here, or just indulge in some retail therapy.
- Chicago Cubs & Chicago White Sox Games – Celebrate your love of baseball by visiting either of the city’s ballparks for their opening day games, usually in early April.
- Chicago Science Fest (mid-May) – with dozens of events, workshops, and speakers, this science-themed event is great for adults and kids. Events are held at top venues throughout the city, including Adler Planetarium.
- Maifest Chicago (late May – early June) – a free, German-inspired cultural festival with food, music, and dancing. It’s a family-friendly event held each year in the up-and-coming Lincoln Square neighborhood.
- Navy Pier Summer Fireworks (Memorial Day – Labor Day) – this event will recur periodically throughout the entire summer, but this perennially popular fireworks show is a major part of Navy Pier this time of year.
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June - August
The heart of summer is the most popular time to visit Chicago, but that also means that hotel prices will be the highest and lines will be the longest. Plan to book ahead as much as possible, too, as many things will sell out quickly. The weather is will likely range between the high 50s and low 80s (mid to high 20s Celsius), but could also have tremendous variation. Here’s a selection of some of the most popular things to do in Chicago in the summer:
- Lake Cruises (June – August) – take a leisurely sightseeing cruise on Lake Michigan to enjoy the beautiful weather and play the tourist without much effort.
- Grant Park Music Festival (June) – this free event offers some of the best classical music performances in the city in one of our most beloved parks. Spend a day at the Art Institute, and then enjoy a performance with a picnic dinner in the evening.
- Hyde Park Brew Fest (early June) – an adult-friendly event, this beer-sampling weekend is a good way to relax after a day spent with the kids at the nearby Museum of Science and Industry.
- Taste of Chicago (July) – come sample the city’s tastiest cuisine alongside foodie locals at this gorgeous lakefront location in Grant Park. Enjoy dance and music performances as you munch.
- Lollapalooza (August) – a pricey event to be sure, but it’s one of the country’s most popular music festivals and is worth the price of admission to see your favorite act in this legendary setting.
September – October (Best Time to Visit)
The summer crowds have mostly died down, and the temperatures will mellow out without getting too frigid just yet. You can expect the day to be somewhere around the high 60s to high 70s (low 20s Celsius), but at night it can get pretty chilly so definitely wear or pack layers. You should also keep in mind that some tours may switch to winter hours (or stop operation altogether). If you’re in town in early fall and looking for things to do, check out our top picks:
- Chicago Architecture Biennial (begins in September) – this event only pops up every two years, but it’s worth the opportunity to explore the fantastic architecture of Chicago. Visit the Chicago Architecture Center or take an architecture cruise to complete the experience.
- Donut Fest at the Zoo (early September) – Lincoln Park Zoo hosts this family-friendly event, offering behind-the-scenes animal access alongside drinks for the adults and donuts for all.
- Chicago International Film Festival (mid October) – held at various locations throughout the city, this highly regarded indie film fest showcases the best in the media and is a must-do for film buffs.
- Chicago Marathon (mid October) – while you may not be running this iconic race, it’s worth a few moments of your time to cheer on these amazing athletes and their quest for glory.
- Sightsee up High – one of our favorite things to do in the fall is to see the city from above. Check out 360 CHICAGO, for one, to see the fall foliage and the changing lakefront neighborhood.
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November – March
The coldest time of the year in Chicago and the least popular time for tourists to visit, the winter can be a real doozy. Temperatures can vary significantly, with everything from periodic days in the 40s to sub-zero temps (single to negative digits Celcius and Farenheit). Dress warmly, but hide inside at museums and other attractions where you can. There are still plenty of great winter events in Chicago, including some of my personal favorites:
- Meet the Animals – Among the best places to stay away from the chill while also taking advantage of the thinner crowds is the Shedd Aquarium. It’s difficult to get in without long lines in the summer, so a wintertime visit is perfect.
- Magnificent Mile Lights Festival (late November) – a prelude to the holiday season, this exciting festival illuminates the city’s most popular shopping district. Grab some hot cocoa before you watch the parade, though.
- McDonald’s Thanksgiving Day Parade (Thanksgiving Day) – with a bevy of themed balloons and floats, this parade is beloved among children and families. Plan ahead if you want to find a space along the parade route.
- Christkindlmarket (mid November – end of December) – visit one of the most popular indie holiday shopping destinations in the city in search of some unique crafted object. Don’t miss out on the souvenir cider mug, either.
- ZooLights (end of November – early January) – a long-standing tradition in Chicago, the Lincoln Park Zoo lights up the night with its animal-themed illuminations. If you’re looking for more things to do in the park during the day, then you could also consider the Chicago History Museum.
- St. Patrick’s Day Parade & Festivities (St. Patrick’s Day) – One of Chicago’s favorite holidays is St. Paddy’s Day, a time when everyone comes together to celebrate their Irish heritage, real or imagined. They also famously dye the Chicago River green, so come for the pictures if nothing else!
Save on Admission to Chicago Activities & Attractions
Plan your trip during the best time to visit Chicago, or brave the weather and forge ahead with a winter trip or summertime sojourn. Regardless of when you visit the Windy City, you’ll want to be smart about your budget. Pick up a Go Chicago pass to save on admission to many of the city’s top attractions so you’ve got more money in your pocket for popular festivals and events. This all-digital, smartphone-friendly pass is the easiest way to see Chicago and save.
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