This month in Chicago kicks off a fantastic summer season. The are plenty of June events happening in the city that embrace the longer days and livelier nights.
From neighborhood food festivals and beach parties to Juneteenth celebrations and Pride Month events, June brings the kind of energy that defines summer in Chicago.
Check out the best things to do this month in Chicago with this local guide.
The Best Things to Do in Chicago This June
Use the navigation below to see what’s happening in Chicago in June 2025. Skip to big events, some classic must-dos, and my handpicked recommendations for what to do this month. Keep an eye out! Events might change, and I might throw in some fun surprises just for kicks!
Top Events: Must-attend events of the month.
Recurring Activities: Regular events worth adding to your calendar.
The Curated List: Personal recommendations for unique Chicago experiences.
Top June Events & Festivals in Chicago
Discover the biggest and most popular June events in Chicago. From Chicago neighborhood festivals to affordable and free things to do.
June Chicago Street Festivals
June | Various Locations
June kicks off an exciting season of street festivals and cultural celebrations across Chicago. Highlights include:
June 1: Windy City Hot Dog Fest
June 1: Do Division Street Fest
June 6 – 8: Lincoln Park Greek Fest
June 6 – 8: Chicago Blues Festival
June 6 – 8: Ribfest Chicago
June 7 – 8: Gold Coast Art Fair
June 7 – 8: Annual 57th Street Art Fair
June 11 – Aug 16: Grant Park Music Festival
June 12 – 15: Puerto Rican Fest
June 13 – 15: Andersonville Midsommarfest
June 13 – 15: Taste of Randolph Street
June 14 – 15: Old Town Art Fair
June 14 – 15: Wells Street Art Festival
June 20 – 22: Summer Smash
June 21 – 22: Chicago Pride Fest
June 21 – 22: Vegandale Fest
June 27 – 28 Chicago Taco & Tequila Fest
June 28 – 29: Millennium Art Festival
Chicago Pride Month Events
June 2025 | Various Locations
Celebrate LGBTQ+ Pride throughout Chicago with a full calendar of events during Pride Month. The highlight is Chicago Pride Fest and the massive Pride Parade in Northalsted, featuring colorful floats, performances, and community gatherings. Other events include parties, art exhibitions, and family-friendly activities celebrating diversity and inclusion.
Here are a few events to check out this month
- Sip for a cause at Renaissance Chicago Downtown Hotel with Pride Month cocktails benefiting Kiki Queens at Staytion Market & Bar and Raised, An Urban Rooftop Bar.
- Dive Into Pride at InterContinental Chicago Magnificent Mile, featuring a pool party with Naysha Lopez, drag history exhibit, movie nights, and donation-based hotel stays.
- Celebrate with a drag brunch and queer winemakers at Beity, Chicago’s Lebanese tasting menu restaurant, with proceeds going to Brave Space Alliance.
- Raise a glass at 4EG bars across Chicago all June long with $1 from specialty cocktails going to the Center on Halsted. aliveOne | Central Park Bar | Easy Bar | Estelle’s | Remedy | The Getaway | The Owl
- Art of Pride in Hyde Park is a free afternoon event bringing together LGBTQ+ artists, performers, and makers.
James Beard Awards® Week
June 13th – 17th | Various Locations
The prestigious James Beard Awards return to Chicago with a full weekend of culinary celebrations. The 2025 event honors the 35th anniversary of the Awards and the 10th year hosted in Chicago. This food-focused festival includes public events ranging from high-profile chef collaborations and exclusive dinners to educational panels and large-scale tastings.
Juneteenth Celebrations in Chicago
June 19th | Various Locations
Celebrate Juneteenth in Chicago, honoring African American freedom and culture with music, food, dance, and community events across the city. From parades to live performances and local markets, this day is rich with history and vibrant festivities.
Chicago SummerDance
June – September 2025 | Various Locations
Dance under the stars at Chicago SummerDance, a beloved free event series featuring live music and dance lessons in parks across the city. From salsa and swing to line dancing and bachata, each event invites participants of all skill levels to learn a new style and enjoy vibrant community celebrations. Expect themed nights, cultural showcases, and family-friendly activities throughout the summer.
Millennium Park Summer Music Series
June – August | Jay Pritzker Pavilion, Millennium Park
This free concert series brings a diverse lineup of local and national artists to one of Chicago’s most iconic outdoor venues. Held on select evenings, the Millennium Park Summer Music Series features a diverse range of music, from jazz and indie rock to global rhythms and experimental sounds. Bring a blanket, pack a picnic, and enjoy warm nights filled with live music in the heart of downtown.
Maxwell Street Market
June – October | West Maxwell Street &, S Halsted St
On select Sundays, enjoy this free event in Chicago. The Maxwell Street Market will open and include an eclectic mix of foods and finds. This year’s edition will also feature live entertainment and programming from cultural partners, and will incorporate nearby businesses and restaurants, including several “Maxwell Street originals” with longstanding ties to the neighborhood.
Chicago Farmers Markets
June – October | Various Locations
Now through the fall, you can find fresh fruit, vegetables, flowers, baked goods, and more at various neighborhood farmers’ markets in the city of Chicago.
Summer Saturday Fireworks at Navy Pier
June – August | Navy Pier
If you’re looking for free things to do in June in Chicago, nothing beats watching the summer fireworks at Navy Pier. This outdoor event is perfect for groups of all ages to enjoy.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
Ongoing Chicago Events to Experience in June
Looking for fun activities and things to do in Chicago in June? Explore this list of ongoing events and experiences happening all month long.
- Architecture Boat Tour: Experience Chicago’s stunning skyline on a Chicago boat tour, a perfect outdoor activity for warm weather.
- Chicago Crime & Mob Bus Tour: Step into the city’s darker history and discover infamous crime spots.
- The Escape Game Chicago: Solve puzzles in immersive escape rooms in downtown Chicago.
- Skydeck Chicago & Navy Pier Ferris Wheel: Marvel at the city’s skyline from these landmarks at wallet-friendly prices.
- See your favorite sports team live: Grab great seats for a Chicago Cubs or White Sox game.
- Interactive Museums: Capture Insta-worthy photos in interactive museums like the Museum of Ice Cream or the colorful Color Factory.
- Museum Free Days: Take advantage of free or discounted admission at museums.
The Curated List of Chicago Events in June
Here’s The Haute Seeker’s curated list of the best events, activities, and coolest events to check out during Jun.
Race Against Gun Violence
What: Now in its 12th year, this community-driven race unites people from across the city to support grassroots organizations working to end gun violence in Chicago. Hosted by Strides for Peace, the event features multiple race options—8K, 5K, and a 2-mile walk—alongside live programming and resource sharing just ahead of National Gun Violence Awareness Day.
When: June 5, 2025
Link for more information: Race Against Gun Violence
Kendrick Lamar and SZA – Grand National Tour
What: Experience a once-in-a-lifetime performance as Kendrick Lamar and SZA take the stage together for a one-night-only stop in Chicago as part of their highly anticipated Grand National Tour.
When: June 6, 2025
Link for more information: Grand National Tour
Oddities & Curiosities Expo
What: Explore the strange and unusual at this traveling expo featuring taxidermy, skulls, horror art, sideshow performers, and more. With vendors from across the country, the event celebrates all things weird in a community-focused, DIY atmosphere. When: June 7–8, 2025
Link for more information: Oddities & Curiosities Expo
Jazz + Gumbo feat. BILAL
What: Experience a night of neo-soul and jazz from acclaimed artist Bilal, paired with gumbo from award-winning Chef Rah as part of the Jazz + Gumbo series—a Chicago-based concert experience inspired by New Orleans music and cuisine.
When: June 8, 2025
Purchase Tickets: Jazz + Gumbo feat. BILAL
Black Yacht Weekend
What: Black Yacht Weekend 2025 is a festival packed with more surprises, parties, and the biggest yacht day ever in Chicago.
When: June 19 – 22, 2025
Link for more information: Black Yacht Weekend
2025 Chicago Dragon Boat Race for Literacy
What: The Chicago Dragon Boat Race for Literacy returns with 33 teams competing in beautifully decorated boats along the Chicago River. Now in its 24th year, the event celebrates Asian culture and supports local literacy programs. It’s a family-friendly tradition hosted by the Chinatown Chamber of Commerce.
When: June 21, 2025
Link for more information: 2025 Chicago Dragon Boat Race for Literacy
Malt Row on Damen
What: Sip and stroll through Ravenswood at this evening tasting event, where local breweries, distilleries, and wineries partner with neighborhood businesses to showcase the area’s vibrant small business community. Wristband includes a tasting glass, punch card, tote bag, and more.
When: June 25, 2025
Link for more information: Malt Row on Damen
Motoblot
What: Celebrate motorcycle culture, music, and vintage style at this three-day rally and street fest. Featuring bike shows, live rock ‘n’ roll, vendors, and community rides, Motoblot is a summer staple for gearheads and music lovers alike.
When: June 27–29, 2025
Link for more information: Motoblot
Cars at Lincoln Common
What: Admire vintage racecars and British classics at this community car show, held just before the Goodwood Festival of Speed. The event includes rooftop displays, complimentary parking for registrants, and a morning full of car culture in the heart of Lincoln Park.
When: June 28, 2025
Link for more information: Cars at Lincoln Common
June in Chicago: What to Expect (and Wear)
What’s the weather like in Chicago during June?
June in Chicago feels like the official start of summer. Expect warm temperatures ranging from the low 70s to mid-80s°F (21–29°C), with plenty of sunshine and the occasional rain shower. It’s the perfect time for lakefront strolls, rooftop dining, and outdoor festivals—but pack light layers just in case.
Is June a good time to visit Chicago?
Is June a good time to visit Chicago?
Definitely! June kicks off Chicago’s busiest, and most exciting season of the year, summer! The month is filled with neighborhood festivals, free concerts, beach days, and cultural events all over the city.
What should I wear in Chicago in June?
What should I wear in Chicago in June?
Toss on a tee, grab your favorite summer dress or shorts, and you’re good to go. Just don’t forget a jacket and an umbrella, Chicago weather loves a surprise, especially in the evenings.
What to Look Forward to in June
If June is the kickoff, July is the main event. Expect even more summer festivals, lakefront fun, fireworks, and food-focused happenings as the season heats up. You won’t want to miss a minute.
