There’s no month in Chicago that isn’t festival month, this city always finds something to celebrate. With world-renowned events dedicated to food, music, culture and art, you’ll never be stuck for something fun to do. During the summer months, festivals in Chicago take advantage of warmer climes with outdoor food fests and alfresco gigs every single weekend. Winter festivals get cosy with campfire themes and many indoor markets to browse. Then spring and fall offer pretty much everything in between.

Whether you’re a local, passing through or on your city break, here’s our recommended list of festivals in Chicago we think you should visit:  

Taste of Chicago

Chicago has a lot of good grub to offer, if you haven’t tried it yet check out our guide to the Best Restaurants in Chicago. From the legendary deep-dish pizza and the upscale burger joints to fine-dining fusions and a cut of steak you won’t forget in a hurry. For a few days in July, Taste of Chicago is the world’s largest free-admission food festival, so definitely makes the list of festivals in Chicago we recommend. There’s local fare as well as international cuisine to sample with more than 82 of the city’s best restaurants participating. Learn the tricks of the trade at a cooking demonstration and chill out at the CH Vodka Cocktail Lounge. Check out local artists work, watch a dance performance and catch a gig from an act you recognise. All. For. Free. Hence why Taste of Chicago is top of the list. 

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Taste of Chicago in Grant Park:
The Big Loop – Red Route, Stop: Hilton Chicago & Grant Park

Lollapalooza Chicago

If your idea of a fun festival in Chicago involves alternative rock, heavy metal, punk, hip-hop and electronic music, Lollapalooza Chicago is your ticket. Created back in 1991 by Jane's Addiction singer Perry Farrell as a farewell tour for his band, Lollapalooza Chicago today is a four-day iconic music fest hosting over 400,000 people each year. Previous years featured the likes of Ariana Grande, Childish Gambino, The Strokes and The Chainsmokers. Held in Grant Park right on the bank of Lake Michigan, the setting alone is pretty special. With 8 stages and more than 170 bands, delicious festival food from Chow Town, interactive areas with giveaways and even a mini-fest for the kids, Lollapalooza Chicago is one festival in Chicago not to be missed. Tickets always sell-out fast, so be sure to bag yours early.

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Lollapalooza Chicago in Grant Park:
The Big Loop – Red Route, Stop: Hilton Chicago & Grant Park

Chicago Blues Festival

Now in its 37th year, the Chicago Blues Festival pays homage to the genre’s past, present and future. This Chicago-born music tradition plays out in front of half a million blues fans, featuring some of the most admired musicians alongside up-and-coming talent. B.B. King and Buddy Guy to Etta James and Koko Taylor have all graced the stage. Held at the Jay Pritzker Pavilion, this genres contribution to soul, R&B, gospel, rock, hip-hop and more is showcased over 3 days in June across six stages with admission absolutely free. Bring along your blanket and a picnic, secure your spot for the day and watch the Chicago Blues Festival play out.

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Chicago Blues Festival at the Jay Pritzker Pavilion in Millennium Park:
The Big Loop – Red Route, Stop: Maggie Daley Park

So there you have our top three recommended festivals in Chicago. A city with a packed events calendar all year round, there really is no bad time to visit. And when you’ve tasted something delicious at Taste of Chicago, listened to a favourite band at Lollapalooza Chicago and swayed along to the blues at the Chicago Blues Festival, you can sit back and relax on a Big Bus tour for a day or two of sightseeing. For more ideas on how to fill the rest of your time in the Windy City, check out our 3 Days in Chicago itinerary.