30 of the Best Things to Do in Chicago This June

From food festivals to outdoor concerts, here are 30 can’t-miss events kicking off summer in Chicago.


June 1-2: Gold Coast Art Fair

Shop from more than 200 juried artists at this annual festival, which will raise funds for Bright Pink, an organization that “helps to save lives from breast and ovarian cancer by empowering women to know their risk and manage their health proactively.” Grant Park’s Butler Field, South Lake Shore Drive and East Monroe Street, Chicago

Begins June 6: Food Truck Thursdays

Dine on food from a variety of food trucks as you enjoy live music, challenge your friends to a game of cornhole, and more on Thursdays through Sept. 12 (except July 4). Dean Avenue between Roger Williams and St. Johns avenues, Highland Park; Jens Jensen Park, 486 Roger Williams Ave., Highland Park

June 7-9: Bears100 Celebration Weekend

Celebrate 100 years of the NFL and the Chicago Bears with player appearances (the entire 2019 team, as well as Hall of Famers Gale Sayers, Dick Butkus, Mike Ditka, and Brian Urlacher and alumni like Matt Forte, Devin Hester, Jim McMahon, and Charles Tillman, are scheduled to attend), panels, activities, and more. Donald E. Stephens Convention Center, 5555 N. River Road, Rosemont

June 7-9: Andersonville Midsommarfest

Chicago Events: Andersonville Midsommarfest
Photo by Starbelly Studios.

Enjoy live music, a drag show, food vendors, shopping, and more. Friday: Clark Street between Summerdale and Catalpa, Chicago; Saturday-Sunday: Clark Street between Foster and Catalpa, Chicago

June 8: Jonathan Van Ness: Road to Beijing

Attention “Queer Eye” fans — Jonathan Van Ness is going on tour and it’s not to be missed. The Chicago Theatre, 175 N. State St., Chicago

June 8: Digestive Health Foundation Gala: Celebrating the Power of Family

Actress, writer, and director Bonnie Hunt will emcee this event, which raises funds for hereditary digestive diseases research. Four Seasons Hotel Chicago, 120 E. Delaware Place, Chicago

June 14: FEW Fridays

Join FEW Spirits for cocktails, food, and live music in their alley on the second Friday of each month (May through September). FEW Spirits Distillery, 918 Chicago Ave., Evanston

June 14-15: Craft Brews at the Zoo

Chicago Events: Craft Brews at the Zoo — Lincoln Park Zoo
Photo courtesy of Lincoln Park Zoo.

Explore Lincoln Park Zoo after hours while sampling craft beers throughout the grounds, playing lawn games, and more. Lincoln Park Zoo, 2001 N. Clark St., Chicago

June 14-16: Ribfest Chicago

Try ribs from Chicago Q, City Barbeque, Famous Dave’s, Wrigley BBQ, and more before voting for your favorite. Plus, enjoy live music and family-friendly activities. Lincoln Avenue from Irving Park Road to Berteau Avenue, Chicago

June 15: Chicago Taco & Tequila Fest

Don’t miss this brand new event featuring tequila tastings; tacos from Aztec Daves Food Truck, Carnivale, Tandoor Char House, and more; music; a silent disco; volleyball, bocce ball, and life-size billiards; and more. 2500 N. Cannon Drive, Chicago

June 15-16: Brickworld®

View intricate LEGO® creations (and build your own), watch LEGO robots battle each other, buy accessories, and more. Renaissance Schaumburg Convention Center, 1551 N. Thoreau Drive, Schaumburg

June 21-23: Strawberry Festival

Love strawberries? Then don’t miss this festival featuring strawberry-infused food and drink, a strawberry pie-eating contest, live music, and carnival games. Stempel Parking Lot, 308 Old McHenry Road, Long Grove

June 22: “Seven Things I’ve Learned”: An Evening with Ira Glass

Hear from “This American Life” host Ira Glass as he shares stories (mixing them live) and lessons he’s learned over the years. Auditorium Theatre, 50 E. Ida B. Wells Drive, Chicago

June 22-23: Fountain Square Artisan SummerFest

This annual fest is set to celebrate 40 years with nearly 100 juried artists, new wine and spirits tastings, kids activities, pet adoptions, street musicians, food, and more. Intersection of Sherman and Church streets, Evanston

June 22-23: Chicago Pride Fest

Chicago Pride Fest
Photo courtesy of Choose Chicago.

This festival features live music, more than 100 vendors, food and drink, and more the weekend before the Chicago Pride Parade. Halsted Street from Addison to Grace Street, Chicago

June 23: Evanston Garden Walk

Now in its 30th year, this garden walk gives you a chance to explore nine private and public gardens (even one on the National Registry of Historic Places). Proceeds benefit scholarships for Evanston Ecology Center’s summer camps and Apiary. Evanston

June 26: Inferno Fest

Find out how much spicy food you can handle at this festival, taking place during the Highwood Evening Gourmet Market. Everts Park, 130 Highwood Ave., Highwood

June 29-30: Adults-Only Campout

Chicago Botanic Garden
Photo courtesy of Chicago Botanic Garden.

Camp at Chicago Botanic Garden and choose from activities like evening yoga, a tram tour, a bird walk, and more, plus enjoy a continental breakfast in the morning. 1000 Lake Cook Road, Glencoe


Begins June 4: Millennium Park Summer Film Series

On Tuesday nights throughout the summer, watch movies under the stars on a 40-foot LED screen. The series begins June 4 with “Black Panther.” Jay Pritzker Pavilion, 201 E. Randolph St., Chicago

June 27-29: “Harry Potter and the Prisoner of Azkaban” in Concert

Watch the third Harry Potter movie as the Chicago Symphony Orchestra performs the score live. Symphony Center Chicago, 220 S. Michigan Ave., Chicago


June 19, 26: Jazzin’ at the Shedd

Chicago Events: Jazzin at the Shedd
Photo courtesy of Shedd Aquarium.

Listen to jazz and enjoy a drink with stunning skyline views every Wednesday through the end of August. Shedd Aquarium, 1200 S. Lake Shore Drive, Chicago

Ongoing: Silver Screen to Mainstream: American Fashion in the 1930s and ’40s

Chicago History Museum: From Silver Screen to Mainstream
Photo by Sean Su.

Visit the Chicago History Museum to view gorgeous dresses from designers like Chanel, Vionnet, and Howard Greer. And on June 22 you can go on a walking tour of Fishman’s Fabrics. Chicago History Museum, 1601 N. Clark St., Chicago


Begins June 4: Starlight Concerts in the Park

On Tuesday nights from June 4 to July 30, enjoy free concerts, family activities, and food trucks at parks throughout Evanston. Various

June 11-12: Lionel Richie

Lionel Richie joins Chicago’s JC Brooks Band for two nights at Ravinia, so get ready to sing along to hits like “All Night Long,” “Hello,” and “Endless Love.” Ravinia Festival, 418 Sheridan Road, Highland Park

Begins June 12: Grant Park Music Festival

Chicago Events: Grant Park Music Festival
Photo by Christopher Neseman.

The 85th season of this concert series will include the annual Independence Day concert, a viewing of “The Wizard of Oz,” and “Swan Lake.” Various

June 21-22: Winnetka Music Festival

This festival returns for its third year with two main stages and a family stage, food trucks, a new acoustic cafe, and more. This year’s lineup includes Moon Taxi, Dorothy, Spencer Ludwig, and John Splithoff. Downtown Winnetka


Opens June 29: “The Music Man”

Don’t miss this classic musical with songs like “Goodnight My Someone,” “Seventy-Six Trombones,” and “Gary, Indiana” directed by Tony Award-winner Mary Zimmerman. Goodman Theatre, 170 N. Dearborn St., Chicago

Media Sponsorships

Make It Better is a proud media sponsor of these events:

June 8-9: Printers Row Lit Fest

If you’re passionate about books, don’t miss this book fair, now in its 35th year, with readings, kids programming, vendors, and more. Printers Row, Dearborn Street from Polk Street to Ida B. Wells Drive, Chicago

June 9: Alzheimer’s Association Greater Illinois Chapter’s Power of Purple

Alzheimer’s Association Chief Science Officer Maria C. Carrillo, Ph.D., will discuss the impact of Alzheimer’s on women during this garden party luncheon. Galleria Marchetti, 825 W. Erie St., Chicago

Additional events Make It Better is proud to support:

Anna Carlson writes the weekly Weekend 101 column and monthly Recommended Events. A graduate of the University of Missouri, her work has been published in Chicago Parent, Inside Columbia Magazine, and Central California Parent Magazine. She is a proud supporter of St. Jude Children’s Research Hospital