40 Fun Things to Do in Chicago in June

June is what Chicagoans wait all year for. Longer days, more sunshine, and shorts weather means that we can enjoy our outdoor spaces to the fullest from the lakefront to the outdoor patio. June is a great time to visit Chicago because the festival season is stacked with events almost every day, yet the crowds and humidity of peak summer are a few weeks away.

I’ve lived in Chicago for nearly two decades, and I love June in Chicago because everyone is outdoors enjoying the city. From Pride Month to Juneteenth to our famous street festivals and block parties, there’s so much to do all month. Whether you’re visiting Chicago in June or you live in Chicagoland, here are 40 fun things to do in Chicago in summer.

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Fun Things to Do in Chicago in June

1. Visit AIDS Garden Chicago

Kick off Pride Month by strolling or biking AIDS Garden Chicago in Lakeview. Located along Lake Michigan near Belmont Harbor, the 2.5-acre park memorializes the early days of Chicago’s HIV epidemic through reflective and educational areas. You can’t miss ‘Self-Portrait,’ the 30-foot sculpture by Keith Haring.

2. Get Moving for Chicago Dance Month

From tap to Bollywood to flash mobs, there are countless ways to move your body during Chicago Dance Month. Take free classes and attend free performances at Navy Pier downtown and Palmisano Park in Bridgeport throughout the month.

3. Chicago Blues Festival – June 5-8, 2025

Blues fans from all over the world converge on Millenium Park every June for the world’s largest free blues festival. Don’t miss Mavis Staples, a B.B. King Centennial Tribute, and a Women in Blues Tribute to Denise LaSalle at the Chicago Blues Festival.

4. Lincoln Park Greek Fest – June 6-8, 2025

St. George Greek Orthodox Church was established in Lincoln Park back in 1923, so it’s no wonder it celebrates culture and tradition at Lincoln Park Greek Fest. Savor Greek cuisine from souvlaki to baklava while you enjoy traditional music and dancing.

5. Rib Fest – June 6-8, 2025

Nothing signals summer like the smoky scent of grilled meats at a sunny street festival It’s no surprise that Ribfest Chicago remains so popular in its 25th year. Head to Northcenter to sample ribs from nine different vendors and add a whiskey tasting while you’re at it.

6. Treat Dad to a Memorable Father’s Day in Chicago

Your dad deserves a day as unique as he is. I shared some ideas for spending Father’s Day in Chicago in this video, including visiting a vertical farm, blues museum, science supply store, and turtle racing!

7. Beyond Wonderland – June 7-8, 2025

Journey down the rabbit hole at this electronic music festival at Northerly Island on Lake Michigan downtown. Afrojack, Illenium, and more will be your soundtrack to Beyond Wonderland’s world of wonder and delight.

8. 57th Street Art Fair – June 7-8, 2025

Head to Hyde Park to get inspired at the Midwest’s longest running juried art fair. The 57th Street Art Fair features work from more than 200 artists and blues music at this free festival that’s been a community favorite for more than 75 years.

9. See Chicago from New Heights by Helicopter

If you’re looking for a truly unique date night or gift idea, try seeing Chicago by helicopter. Admire the city from a 45-minute helicopter ride past iconic downtown sights like Millennium Park and Navy Pier. I treated my husband to a helicopter ride for his birthday and timed it at sunset for jaw-dropping views of Chicago that you can’t get anywhere else!

10. Puerto Rican Fest – June 12-15, 2025

Wepa! It’s time to celebrate Chicago’s vibrant Puerto Rican community at the Puerto Rican Festival in Humboldt Park. Enjoy traditional music, food, and fun at the festival all weekend. The parade kicks off from Division and Campbell at noon on June 14. Even if you don’t attend the festival, don’t miss informal parade of Puerto Rican pride down Division Street all weekend.

11. Chicago Arts District Second Friday – June 13, 2025

One of the first events I attended after moving to Chicago was Second Friday in Pilsen. Meeting local artists and exploring their galleries is as fun today as it was then. Pick up a map at the information center at 1945 S. Halsted and gallery hop from 6-10 p.m.

12. Taste of Randolph – June 13-15, 2025

The West Loop’s restaurant scene has come a long way since the Taste of Randolph started 28 years ago. Taste your way through the neighborhood with 17 food vendors and three days of music including Phantogram, Spitalfield, and Chromeo.

13. Andersonville Midsommarfest – June 13-14, 2025

Celebrate Andersonville from its Swedish roots to its proud LGBTQ+ community at Midsommarfest. Support vendors from Andersonville’s small business community and enjoy music by local favorites like Facs and the O’My’s.

14. Rock Out at a Chicago Blues Club

The blues weren’t invented here, but the music thrived as African Americans moved to Chicago during the Great Migration. That legacy continues today with a thriving community of blues musicians and clubs. My favorite blues clubs in Chicago are Buddy Guy’s Legends, where the legend himself has a residency every January and is often hanging out at the club; Rosa’s Lounge, a family-run club in Logan Square; and Kingston Mines, offering two stages and late night dance parties in Lincoln Park.

15. Watch a Movie in the Park

Watching a movie in your local park with a picnic is peak Chicago summer. I have fond memories of meeting with friends and my husband and enjoying summer in the city together with a movie. Movies in the Park takes place in parks throughout the city and they range from kid movies to campy to classics. I have my eye on Raiders of the Lost Ark playing in Bartelme Park in the West Loop on June 16.

16. Cruise with a View on an Architectural Boat Tour

There’s no Chicago summer tradition like taking an architectural boat tour on the Chicago River or Lake Michigan. Even though I live here, I take at least one every year and I always learn something new! Come for the views and leave with a new appreciation for Chicago history. Did I mention there’s a bar on board? My favorite boat tour is by Chicago’s First Lady, since it’s run by the Chicago Architecture Center. Wendella and Shoreline Sightseeing also give great tours. For the best Chicago skyline views book a sunset boat tour on Lake Michigan.

17. Bronzeville Juneteenth Festival – June 14, 2025

This Bronzeville festival celebrates the end of slavery in the U.S. with a day of unity and culture. The fifth annual Juneteenth Celebration features small businesses, live music and cultural performances, food, history, art, and family fun. The celebration takes place from 35th through 37th and King Drive.

18. Artists of the Wall Festival – June 14-15, 2025

Watch artists at work along Lake Michigan at the annual Artists of the Wall Festival. Artists and Chicagoans repaint part of a 600-foot-long wall located near Loyola Beach every year, adding their colorful spin on the local spot. It’s free to attend and watch art in action.

19. Wells Street Art Festival – June 14-15, 2025

Not to be confused with the Old Town Art Fair, the Wells Street Art Festival takes place in Old Town on Wells St. from North Ave. to Division St. This year marks the 50th anniversary of the fest that features work from more than 130 artists along with food, music, and fun.

20. Old Town Art Fair – June 14-15, 2025

The Old Town Art Fair has been a beloved Chicago festival for 75 years and counting. Head to the Old Town Triangle Historic District near Lincoln Park to admire works from more than 200 artists, walk some stunning gardens, and hear live music.

21. Father’s Day Whiskey and Cigar Fest – June 15, 2025

Give dad what he really wants this Father’s Day with a Whiskey and Cigar Fest at Dearly Beloved on the Near North Side. From 5-8 p.m. you’ll enjoy two craft whiskey cocktails and one premium cigar and the best gift—quality time together.

22. Listen to an Outdoor Concert at Ravinia Festival

Did you know that Ravinia Festival is the oldest music festival in North America? Taking the Metra to Highland Park with picnic supplies in tow is one of Chicago’s favorite summer traditions. Ravinia has more than 100 shows each summer, including the Roots, Kygo, and Chicago Symphony Orchestra.

23. Summer Smash – June 20-22, 2025

A trip to the burbs is worth it to see hip hop stars like Chance the Rapper, Future, and young Thug perform at the Lyrical Lemonade Summer Smash. Head to Seatgeek Stadium in Bridgeview for three days of rap with nearly 50 artists ranging from Sexxy Red to Insane Clown Posse.

24. Far South Side Juneteenth Festival – June 21, 2025

Far South Side communities come together to celebrate at Juneteenth Festival. Join the fun in West Pullman for a free, family-friendly event featuring live music, food from local Black-owned restaurants, business and housing workshops, and a small business marketplace.

25. Admire the Oakland Museum of Contemporary Art

If you’re looking for inspiration, try strolling the free, outdoor Oakland Museum of Contemporary Art. The late artist Milton Mizenberg Jr. created sculptures from scraps of wood and helped transform his street in the Oakland community. Don’t miss his bronze sculpture nearby in Williams-Davis Park.

26. Have Sustainable Fun at Re:Fest 2025 – June 21, 2025

The Rebuilding Exchange in Bucktown hosts Re:Fest, Chicago’s premier annual sustainability themed street festival. This is a festival devoted to reclaiming, reusing, remaking and retraining for a more sustainable and future-ready Chicago. There’s a kid zone, live music DIY demos, artisan vendors, food trucks, and a reused material maker competition. Drop off reclaimed materials and pick up the exclusive craft brew RE:Zest APA.

27. Ride Chicago’s Iconic Ferris Wheel

Everyone needs to do it once. The Ferris wheel was invented in Chicago and the nearly 200-foot Centennial Wheel at Navy Pier is still an icon. Grab a ticket, enjoy the views, and soak in this piece of Chicago history.

28. Pride Fest  – June 21-22, 2025

June is filled with Pride events, and Chicago Pride Fest is celebrated the weekend before the city Pride parade. The two-day street fest features a Youth Pride Space for teens, drag performance, a pet parade, dance exhibitions, Chicago Gay Men’s Chorus, guest speakers and over 150 food and merchandise vendors. Don’t miss performances by Jesse McCartney, Deborah Cox, Aluna, and more.

29. Go on a Murder Mystery Walking Tour

Take your love of true crime to the streets with a murder mystery walking tour. Learn about real legends and crimes in Chicago while you try to solve a murder playing detective and suspect in this two hour tour.

30. Isaiah Collier at MCA – June 24, 2025

Tuesdays on the Terrace are Chicago summer tradition at the Museum of Contemporary Art. Enjoy free live music and art on a summer evening when Chicago native Isaiah Collier takes the stage with his saxophone.

31. Chicago Taco & Tequila Fest – June 27-28, 2025

Do I need to say more than tacos and tequila? Chicago Taco & Tequila Fest pops up in Wrightwood Park in Lincoln Park full of bold flavors.

32. All of Us Festival – June 27-28, 2025

All of Us Festival takes over Grant Park with a Pride festival for electronic music fans. Dance along with Disclosure, Arca1000000, James Blake, Cobrah, and more.

33. Festival of Unfinished Work – June 26-28, 2025

Welcome to a theater festival that amplifies artists’ unfinished work. The third annual Festival of Unfinished Work features six short scenes from original full-length plays currently in process, written by Chicago-based playwrights.

34. Craft Brews at the Zoo – June 28, 2025

Have you ever wanted to visit the zoo without the kids? Lincoln Park Zoo becomes adult only for the night at Craft Brews at the Zoo featuring more than 100 craft beers, ciders, and more. 

35. Go on a Pothole Scavenger Hunt

Spending time outdoors doesn’t only mean drinking on patios. If you’re looking for a fun way to explore the city, check out artist Jim Bachor’s pothole art. He makes beauty out of Chicago’s infrastructure issues, and the temporal art is ever changing. His website lists a map of past and current works.

36. Backlot Bash – June 28-29, 2025

Back Lot Bash started in 2004 to promote female artists in the Chicago LGBTQ+ community. The three-day festival in Andersonville features musicians, comedians, and more like JoJo Siwa and Fortune Feimster.

37. Millennium Arts Festival – June 28-29, 2025

This free festival features a juried art showcase of more than 100 artists along Michigan Avenue in the Loop. Enjoy live music, face painting, and food trucks all with stunning views of downtown Chicago at the Millennium Arts Festival.

38. Take a Walk at Sky Landing

June is a great time to take advantage of Chicago’s green spaces, and one of my favorites is Jackson Park in the Hyde Park neighborhood. The park was built for the 1893 World’s Fair, and it features an artwork by Yoko Ono. Sky Landing is a sculpture symbolizing peace that you can appreciate from many angles.

39. Chicago Pride Parade – June 29, 2025

Riding on a float in the Chicago Pride Parade is a core memory. It was beautiful to sing along with thousands of strangers in unison as we celebrated the LGBTQ+ community. The free parade starts at 11 a.m. at North Broadway Avenue and West Montrose Avenue  in Northhalsted and heads south, to West Diversey Parkway and North Sheridan Road in Lincoln Park. It’s one of the world’s biggest Pride parades, so expect a crowd and join in the fun!

40. Sudan Archives at Millennium Park – June 30, 2025

Seeing a concert in Millennium Park with the city skyline around you while Chicagoans dance is a peak summer experience—and it’s free. Don’t miss LA-based violinist and singer-songwriter Sudan Archives close out the month.

Visiting Chicago in June FAQ

Is June good time to visit Chicago?

June is one of the best times to visit Chicago. The days are long, the event and festival calendars are packed, and folks are enjoying the lake and parks. It’s not too hot yet, so the weather is perfect for strolling the city and exploring iconic attractions like the Field Museum, Art Institute, and Skydeck Chicago. You might want to book flights and hotel deals flights and hotel deals in advance as well as reservations at top restaurants. Whether you’re attending Pride or Blues Fest or simply strolling the city, June in Chicago is magical.

What is Chicago weather like in June?

June in Chicago is generally warm but pack a jacket for chilly evenings. According to the National Weather Service, the average temperatures in Chicago in June range from a high of 80 degrees to a low of 60 degrees. Expect sunshine and blue skies interrupted cool breezes coming off Lake Michigan. With rapidly shifting weather, be sure to check the forecast before you visit Chicago in the summer.

What should I wear to Chicago in June?

If you’re wondering what clothes to wear to Chicago in June, expect sunny weather with a lakefront breeze. Warm days can still turn chilly at night, especially near the lake. I recommend wearing layers to be prepared for warm days followed by cool nights. Rain is always a possibility during summer in Chicago. Check the weather forecast before you visit Chicago in June so you can pack appropriately.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the spring.

• Chicago is a walking town, so pack comfortable shoes like sneakers, boots, or sandals. 
• Dress in layers so you can adjust to the different temperatures indoors and outdoors. You may want to layer with a lightweight women’s jacket or men’s jacket.
• A classic button-down Oxford or chambray shirt is great for traveling, and I’ve never met a striped Breton shirt that I didn’t like.
• I typically layer a lighter trench coat, leather jacket, or bomber jacket over my outfit.
• It doesn’t hurt to pack a windproof travel umbrella for rainy days.

Where to Stay in Chicago in June

Wondering where to stay overnight in Chicago in the summer My favorite hotel views are from the Chicago Athletic Association overlooking Millennium Park and the boats on Lake Michigan and the LondonHouse with jaw-dropping views of the Chicago River from the rooftop bar. I love the views of Grant Park from the Blackstone Hotel and the Hilton Chicago. Some of my favorite hotels stays in Chicago are at the luxurious Four Seasons Chicago and Waldorf Astoria Chicago located near the best shopping and dining in the Gold Coast area.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope this helps you enjoy your time when you visit Chicago in June!

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

Find out what to do in Chicago throughout the year:

• Fun Things to Do in Chicago in January
• Fun Things Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April
• Fun Things to Do in Chicago in May