Chicago Summer Street Festival Guide 2018

Chicago Street Festival Guide - Lollapalooza 2018

Food, music, architecture, and art… The city of Chicago really does have it all, but there’s a reason why us locals always tell our friends and family to come visit in the summer. So what makes summer in Chicago so special?

Chicago summer street festivals of course! Starting before Memorial Day and stretching beyond the kiddies returning to school, you can find city streets blocked off and tourists and locals alike heading out each weekend to the many neighborhoods that comprise the Windy City for the best food, drink, crafts, and music each community has to offer.

So how do you get to see it all this summer, and then some? Our handy guide details the best festivals in the city...

Our Favorite Summer Festivals


Chicago Gospel Music Festival | June 1-2 | Chicago Cultural Center & Millennium Park
With Chicago’s deep gospel roots, the Chicago Gospel Music Festival brings locals and national artists back to the city where the genre was born.

Do Division Street Fest & Sidewalk Sale | June 1-3 | West Town 
Nestled in between West Town, Wicker Park, and Ukrainian Village, Division street turns into the best of all three neighborhoods for the weekend, featuring two live music stages, a dedicated Family Fun Fest area, and all the best local food and brews you can get your hands on.

Lincoln Park Greek Fest | June 1-3 | St. George Greek Orthodox Church
Bringing the sounds and tastes from Greece to all of Chicago, the Lincoln Park Greek Fest blends tradition and fun for all cultures.

Hyde Park Brew Fest | June 2-3 | 53rd & Harper
With over 50 different ciders and beer, the Hyde Park Brew Fest showcases some of the best hip hop and house music DJs in the country.

Ribfest Chicago | June 8-10 | Lincoln/Damen/Irving Park Intersection

Voted Chicago’s Best Food Fest, Ribfest Chicago is celebrating it’s 20th anniversary of ribs and Rock & Roll.

Chicago Blues Festival | June 8-10 | Millennium Park

As the largest Blues festival in the world, the Chicago Blues Festival spans three days and four stages in the city that started it all.

44th Annual Wells Street Art Festival | June 9-10 | Old Town

Over 225 artists from across America come to the Wells Street Art Festival, bringing with them everything from sculpture to painting to jewelry.

Grant Park Music Festival | June 13 – August 18 | Grant Park

With performances of Mozart, Brahms, and Haydn, this year’s Grant Park Music Festival is a must listen for anyone with interest in classical music.

Chicago Pride Fest & Parade| June 16-17, June 24 | Boystown

The month of June is LGBTQ Pride Month! A two-day street festival is held the weekend before the parade, both of which celebrate LGBTQ life, culture, and community.

Randolph Street Market Festival | June 23-24 | West Loop

For the best vintage vibes and antique furniture, the Randolph Street Market Festival is full of all things for your home, plus some extra good food for your stomach.

Ravenswood On Tap | June 23-24 | Ravenswood & Berteau

Home to Malt Row, Ravenswood has one of the best craft brewing communities in the country, and they celebrate each summer with Ravenswood on Tap.


Ready to get your summer on? Or ready to move closer to your favorite summer festival so you can experience all the great things of your favorite neighborhood year round? Reach out to the Real Group team – with tons of expertise and connections, the Real Group team can ensure that you’re living your best summer life every day of the year.

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