Events in Chicago, Fun Things to Do in Chicago in the Summer

Erika Davis

Chicago has no shortage of outdoor fun. This summer, there’s an additional cause for celebration as outdoor festivals and large gatherings are back after a pandemic pause. Chicago locals often ask us for recommendations on events they can enjoy during the summer months. Here’s a rundown of festivals that will bring you the best of Chicago.


Maifest Chicago: Jun 2-5. This celebration of German heritage offers traditional food, dancing, live music, and, yes, giant beers.

Chicago Gospel Music Experience: June 4. Gospel was born in Chicago, and this free concert features choirs, contemporary gospel artists, and more.

Wells Street Art Festival: June 11-12. Art lovers can enjoy classic Old Town Chicago and artistic talent galore at this juried festival.

Chicago Blues Festival: June 9-12. This legendary music festival hosts hundreds of thousands of music lovers and features blues icons from around the country.

Chicago Pride Fest: June 18-19. Celebrate Pride with live music, dance, food, and fun in this historic neighborhood.


African/Caribbean International Festival Of Life: July 2-4. Washington Park hosts a celebration of African and Caribbean cultures against a backdrop of Reggae music.

Taste of Chicago: July 8-10. Sample award-winning cuisine in this annual multi-day flavorfest, and enjoy marquee events every night on the main stage.

Pizza City Fest: July 23-24. No Chicago festival list would be complete without Chicago-style pizza. Sink your teeth into deep dish and tavern-style pizza, and enjoy book signings, live music, demos, and more.

Lollapalooza: July 28-31. One of the largest and most well-known music festivals is back at lakefront Grant Park with more than 170 acts.

Chinatown Summer Fair: July 30-31. Celebrate East Asian culture with demonstrations, traditional dances, music, and food from Chicago Chinatown restaurants.


 Windy City Smokeout: Aug 4-7. Nothing says summer like a barbecue. The Windy City Smokeout features top country music artists and all things BBQ.

Wine and Art Walk at Morton Arboretum: Aug 19-21. Enjoy an art fair and wine tasting across sprawling greenery just outside of Chicago. 

Chicago Air and Water Show: Aug 20-21. A fan favorite, this is the largest free show of its kind in the country, with jaw-dropping aerial displays above Lake Michigan.

Years of Chicago Dance Festival: Aug 27. This free, cause-driven showcase features an array of Chicago dance groups and supports the Chicago dance community.


Tuesdays on the Terrace: Experience the sounds of Chicago every Tuesday during the summer. The Museum of Contemporary Art offers free jazz events on its outdoor terrace, highlighting different Chicago artists each week.

Jazzin’ On the Steps: For an extra dose of Chicago’s renowned jazz community, join The South Side Jazz Coalition for free jazz on the steps of St. Columbanus Catholic Church on the fourth Sunday of every month.

Millennium Park Series: Millennium Park offers an ongoing music series and a film series. Enjoy listening to new and emerging artists under the stars or taking in a favorite movie on a 40-foot LED screen.  Both series are free of charge.

Grant Park Music Festival: The 2022 season has something for everyone, from The Grant Park Orchestra and Chorus performing old favorites and new classics to the death-defying Cirque aerialists soaring on stage.

We hope this helps you plan your summer calendar, and we wish you a happy festival season!