Chicago Festival Season is Back!


After a year inside it’s time to finally get on your feet and out in the streets! There’s no better summer activity than music and street festivals and Chicago has got the best of the best. Whether you’re looking to hear live music, taste delicious food, or get up and dance, there’s something for everyone to celebrate this summer. Here are some of our favorite festivals happening this season:

Pride in the Park

Celebrate love at this one-of-a-kind LGBTQ+ festival happening June 26th and 27th. With iconic artists, performers, and drag queens, this star-studded lineup is guaranteed to put on a fabulous show. Pride in the Park is set to be one of Chicago’s first outdoor festivals since the start of the COVID-19 pandemic and we could not be more excited!

Taste of Chicago To Go 

One of The Windy City’s most beloved festivals is returning this summer- with a twist! To ensure public safety, this iconic event will be modified for a second year in a row, but don’t let that discourage you from taking part in one of the largest food festivals in the world. Through a series of pop-up events spanning from July through September, this year’s Taste will feature cooking demonstrations, special events, and more from some of the city’s best restaurants. Come hungry and see what good eats Chicago has to offer. 

Windy City Smokeout 

Come for the music and stay for the food at this summer’s Windy City Smokeout happening July 8th through 11th at Chicago’s United Center. With headlining music acts like Brett Eldredge, Darius Rucker, Dierks Bentley, and Jon Pardi, this festival is one for country music lovers. If that doesn’t convince you, this year’s festival will showcase the best BBQ not just in Illinois, but around the US. 

Grant Park Music Festival 

There’s nothing like summer in the city and there’s no summer in Chicago without the Grant Park Music Festival. All summer long show up to Chicago’s iconic Jay Pritzker Pavilion and enjoy classical entertainment from some of the country’s best musicians. The Grant Park Orchestra and Chorus joined by special guests will provide concert-goers with festival classics from Symphonies to Broadway repertoire. Whether you’re a classical music lover or looking for a new experience, this outdoor concert series is a must!

Millennium Art Festival

If you’re looking to tap into your artistic side, be sure to check out the Millennium Art Festival happening July 16th through 18th! Over 110 artists will be featured with a wide array of mediums including paintings, photography, ceramics, and more. The event is totally free and although reservations are recommended, they are not necessary. Don’t miss this one-of-a-kind Michigan Ave classic!


If there’s one festival you can’t miss, it’s Lollapalooza. After taking a year off, Chicago is ready to bring back one of the world’s largest and most legendary music festivals of all time. Headliners like Miley Cyrus, Post Malone, Tyler the Creator, and more only scratch the surface of what 2021’s lineup has to offer. Happening July 29th through August 1st, you can go for just one day, or go all out and buy yourself a 4-day pass and spend the whole weekend rocking out to some of the best live performances money can buy. 

Summer Smash Festival

Celebrate the best of hip-hop August 20th through 22nd at this year’s Summer Smash Festival happening in Douglas Park. Don’t miss your opportunity to witness some of the most sought-after hip-hop artists in the industry. Featuring performances by A$AP Rocky, Lil Baby, Lil Uzi Vert, and more, Summer Smash is THE premier hip-hop festival of the midwest. 

Glenwood Ave Arts Fest

The Glenwood Ave Arts Fest combines the best all of these festivals have to offer and puts them all in one place for you to enjoy. Join the fun August 20th through the 22nd to experience live music, great food, and craft beer all from local merchants in Chicago’s historic Rogers Park Neighborhood. Art demonstrations, open studios, and work from over 120 talented artists will be featured for your enjoyment.

Whether you’re looking for a high energy concert, a low-key art gallery experience, or just want to try some tasty food, Chicago’s summer festival lineup has something for everybody. Return to old favorites or take our recommendations and try something new! This summer is sure to be one to remember.

Written By: Lindsey LeBeda

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