“Nothing beats Chicago summers, it’s a perfect mix of water, warm weather, shopping and the best eats. It’s like a giant hangout in the best city in the country” says Hazel, born and raised in the Windy City. 

Summer in Chicago is unlike any other. With so much to do, it’s difficult to discern what might be the perfect pastime to fill up the warm sunny days. Each month brings a whole new list of activities, from local farmers markets, to the biggest music festivals—many even come at no cost. 

Here is a list of activities, organized and stress free!

Kicking off in May:

• Sueños Music Festival (May 23–24, Grant Park) – Major Latin music festival with 40+ artists!
• Belmont-Sheffield Music Fest (May 22–24) – Free neighborhood music festival  
• Do Division Street Fest (May 29–31) – Local food + music festival  
• Chicago Farmers Markets begin (mid-May citywide)  

Hazel says that in May “we really start to come out of our winter hideaways, it’s so lively everywhere you go.” Those first few
weeks of farmers markets and music festivals mark the true beginning of summer in Chicago.

As the month progresses, the colors of the rainbow begin to shine brightly all over the city as the Chicago Pride Parades gears up for a month of happy, proud love. Alongside this, music fills the city parks and great food fills our bellies!

• •  Chicago Blues Festival (June 4–7, Millennium Park) – The largest free blues festival in the world!
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  • Ribfest Chicago (June 5–7) – Food + music festival.

• Chicago Pride Fest + Pride Parade (late June) – One of the biggest Pride celebrations!
• Grant Park Music Festival (starts mid-June, free concerts all summer)  

“Once that weather warms up, there’s no getting us inside. Whether it’s food, music, or just a neighborhood walk, there is no shortage of smiles and activities in June” says Hazel, recalling her memories of Chicago summer fun.

July is filled to the brim with things to do. The patriotism that comes with the Fourth of July, the sick beats that come with Summer Smash, and the warm sun that drives everyone to the beach— there truly is something special about this time of year!

• Summer Smash Festival (late June / early July, SeatGeek Stadium) –one of the biggest hip-hop festivals in the U.S., with 50+ artists and huge crowds  
• Taste of Chicago (July 8–12, Grant Park) – massive food festival

• Windy City Smokeout (July 8–12) – country music + BBQ
• Wicker Park Fest (July 24–26) – neighborhood music fest

Hazel says this is peak summer, and that “there really is something for everyone, country music, hip hop, good eats, outdoor fun. It’s everything: crowds, music, food, the atmosphere is so full of life and just pulls you in.”

As summer begins to wind down, the city of Chicago does everything but with some of the most attended events taking place just before everyone goes back to school and normal responsibilities resume. 

In August, here’s what you should expect:

• Lollapalooza (July 30 – Aug 2, Grant Park) – 170+ artists, huge festival 
• Chicago Air & Water Show (mid-August) – free show over Lake Michigan  
• Chicago House Music Festival (Aug 27–30) – celebrates Chicago’s music roots  
• Millennium Park Summer Concerts (all month) – free music shows.

“This is the true Chicago experience. The diversity of culture, the great music, time by the beach, it really is like no other” says Hazel. “There’s something just a train or bus ride away from any point in the city—all the time.”