Must-Do Chicago Summer Festivals

Bring your group to some of Chicago’s most exciting summer food and music festivals. 

As summer brings warm weather and sunny days, Chicago begins to burst with festivals across the city. Bring your group to revel in the vibrant atmosphere and immersive experiences at these landmark events throughout the summer. Bonus: many of these are free festivals, perfect for budget-friendly trips.

FREE Chicago House Music Festival

May 26, 2018, 2-9 p.m.

Chicago House Music Festival

Your group can experience the energy of house music in the city where it was born. The House genre revolutionized electronic dance music across the world, and this free outdoor festival at the Jay Pritzker Pavilion in Millennium Park showcases DJs spinning various forms of house music.

FREE Chicago Blues Festival

June 8-10, 2018, 11 a.m.-9:30 p.m.

As the largest free blues festival in the world, your groups will get to see, hear and dance to blues music of all kinds—from classic performers such as Mavis Staples to blues newcomers like Fantastic Negrito—in Millennium Park, right in the heart of the “Blues Capital of the World.”

Spring Awakening Music Festival

June 8-10, 2018, 1 p.m.-10 p.m.

Spring Awakening

Addams-Medill Park will come to life with the energetic beats of electronic dance music as world-famous DJs (think: Tiësto, Kaskade, deadmau5 and many more) take to the turntables at this multi-stage event. Ages 18 and older.

FREE Grant Park Music Festival

June 13-August 18, 2018, Times vary

Plan a night at the symphony—for absolutely free—when you take your group to a concert at this summer music series held at the Jay Pritzker Pavilion in Millennium Park. Pack a picnic, bring some lawn chairs or blankets, and enjoy an evening in the heart of the city, listening to orchestral music and choral performances under the stars.

FREE Chicago Pride Festival & Parade

June 16-17, 2018, 11 a.m.-11 p.m. (Festival)

June 24, 12 p.m. (Parade)

Chicago Pride Parade

Immerse your group in the vibrant LGBTQ+ culture at this two-weekend pride celebration. The first weekend is an all-out festival with music, entertainment and more along Chicago’s Halsted Street in the Boystown neighborhood. The second weekend is the dazzling Pride Parade, which follows a four-mile route, drawing thousands of spectators.

FREE Taste of Chicago

July 11-15, 2018, Times vary

Original Rainbow Cone Chicago

Foodies won’t want to miss this flavor-filled celebration at Grant Park, where Chicago’s diverse culinary community showcases everything from ethnic dishes to trendsetting cuisine to Chicago’s iconic staples. Live music, arts and entertainment provide plenty to see along the way. Admission is free, but food ticket purchases are required for tastings.

Pitchfork Music Festival

July 20-22, 2018

This all-ages festival features more than 40 bands across three stages, with a focus on new and emerging musical talent, along with long-time favorites. Visitors can discover even more music at the onsite record fair, along withh handmade crafts and more than 20 food vendors. Performers this year include Tame Impala, Fleet Foxes, Kelela, Ms. Lauryn Hill and Chaka Khan.

Windy City Smokeout

July 13-15, 2018, Gates open at 2 p.m. Fri.; noon Sat. & Sun.

Windy City Smokeout

Barbecue, beer and bands is the name of the game at this annual festival at 560 W. Grand Avenue, along the Chicago River. Groups can savor smoky dishes cooked up by award-winning pitmasters, sip on craft beer and jam out to country music stars like Brett Eldredge, Brothers Osborne and Kane Brown.


August 2-5, 2018, 11 a.m.-10 p.m.


A sprawling music festival with eight stages across Grant Park, this four-day event draws more than 170 bands, from big-name performers such as Bruno Mars, The Weeknd and Jack White to plenty of up-and-comers. Gourmet food, an art market and a “Kidzapalooza” rounds out the festival.  

Find even more upcoming Chicago festivals in the events calendar

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