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Things to do in Chicago During May

May will hopefully bring the warm weather to Chicago that we’ve been craving. Rain or shine there’s plenty of fun things to do in the city with many activities being free or low cost. Whether it’s family activities, date night, or a night out with the girls, this list has something for everyone.

Here are a few things to enjoy during the month of May in Chicago!

Check out Loop at Navy Pier

Experience Loop, a FREE, interactive art installation for all ages, in Polk Bros Park! Sit down inside the retro-futuristic machine and activate the mechanism, causing beautiful images inspired by 13 fairy tales to come to life to the sounds of a music box. The Loop art installation runs through May 12, see it before it’s gone! Polk Bros Park, Navy Pier

Hamilton the Exhibition

Statue displays at Alexander Hamilton Exhibition
Hamilton the Exhibition (photo Antonio Perez, Chicago Tribune)

See Alexander Hamilton’s remarkable story through his eyes in this 360-degree immersive exhibition inspired by the revolutionary musical. Get tickets here.NORTHERLY ISLAND • CHICAGO, IL

Free Tuesdays at the Chicago History Museum

Every Tuesday in May, Illinois residents can take in the history of Chicago and hear the stories of the people through interactive exhibitions and public programs for FREE. Chicago History Museum,1601 N Clark St, Chicago

Food Truck Social at Lincoln Park Zoo

Lincoln Park Zoo, Sat, May 11, 7:30 pm: Experience the most excellent meals (on wheels) Chicago has to offer, while also enjoying the zoo after hours. In addition to dozens of food trucks, there will be fun activities, live music, and drinks available for purchase. Lincoln Park Zoo Tickets are $10 here

Chicago Riverwalk Season Celebration

Chicago River
Chicago River Walk

Riverwalk, Monday, May 13-Sunday, May 19: (FREE)The City of Chicago will highlight the Riverwalk’s free summer programming during a public celebration running Monday, May 13, through Sunday, May 19. Activities include Year of Chicago Theatre themed programs, Art on The MART, walking tours led by the Chicago Architecture Center, Fishing at the Jetty led by the Chicago Park District and a pyrotechnic display off of the south drive of the Merchandise Mart on Monday, May 13. For complete details, visit


Free movies at Gallagher Way
Music Box Movies at Gallagher Way

WED, MAY 16TH, 2018 TO WED, SEP 19TH, 2018 (FREE)

Gather your friends and family and come enjoy Gallagher Way’s free summer movie series brought to you by Music Box Theatre.

Kicking off Wednesday, May 16 and running every other Wednesday through September. Relax and picnic as you enjoy classic films such as A League of Their Own, Back to the Future, Home Alone, Twister and more. Gates open at 6:00 pm, screening starts at 7:30 pm. Full Schedule Here Gallager Way: 3635 N Clark St, Chicago

Chicago Antiques, Arts, & Design Show at The Mart

Antiques on display at The Mart
Chicago Antiques at The Mart

May 16-19, 2019 at The Mart The show will feature 75 premier national and international exhibitors presenting fine antiques, decorative and fine arts reflecting all design periods from ancient to 20th-century modern. The Mart Purchase tickets here

Chicago Wine Festival – Lincoln Park Wine Fest 2019

Glass of Red Wine
Over 60 varieties of wines available at Lincoln Park Zoo Wine Festival

Friday, May 17 – Sunday, May 19 Over 60 varieties of wines available for tasting. Tickets include 12 Tastings with each purchase. Beyond samplings, wine connoisseurs will also appreciate hearing the expertise of brand ambassadors and sommeliers. Live music, food-wine pairings, artisans, and the products/services of wine-related vendors will also be present. Tickets are on sale here, however, Groupon currently is offering discount tickets, get them before they’re gone! Jonquil Park

4th Annual House Music Conference and Festival

Friday, May 24-Saturday, May 25 Millennium Park, Jay Pritzker Pavilion (FREE) The Chicago House Music Festival will feature an industry gathering, DJs and live performances showcasing the various sounds and styles of house music. Bust a move and bread a sweat as you celebrate the genre born in Chicago that has gone on to transform dance music internationally.
For a full schedule of events, visit the website:

Live on the Lake, Navy Pier 

Miller Lite Beer Garden at Navy Pier
Miller Lite Beer Garden

May 25, 2019: FREE live music in the Miller Lite Beer Garden will feature local favorites, national touring acts, and exciting new artists all summer long. Navy Pier


  • 2:00PM – 3:00PM & 3:30PM – 4:30PM | The Contenders
  • 5:30PM – 6:30 PM & 7:00PM – 8:00PM | Creedence Revived
  • 9:10PM – 10:00PM & 10:25PM -11:30PM | Soul Commitments

Check out Offshore, the Nation’s Largest Rooftop Lounge

Offshore Rooftop Deck at Navy Pier
Offshore at Navy Pier

Opening sometime around Memorial Day weekend, Offshore’s all-seasons/all-weather venue spans over 36,000 square feet and boasts a full-service bar, world-class kitchen, terraces, seven cozy fire pits, an entertainment and gaming area, and multiple sizeable social gathering spaces. Offshore at Navy Pier

Memorial Day Parade

Memorial Day Parade in Chicago
Memorial Day Parade

Saturday, May 25th (FREE)

Chicago’s Memorial Day Parade honors all men and women who made the ultimate sacrifice in defense of our country. 

The Wreath Laying Ceremony will begin at 11 am on Daley Plaza (Dearborn and Washington Streets). The parade will then step off at noon and proceed south on State Street from Lake Street to Van Buren Street Kickoff at Daley Plaza

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