Now that the gears of summer are finally in motion, the Chicagoland area is brimming with possibilities! This month we celebrate Pride Month, Juneteenth and Father’s Day — and we’ve got festivities surrounding all of those events and more covered in our round-up of the best things to do in Chicago and the North Shore this June.
We want to see how you’re spending your summer! Don’t forget to tag us in your post on Instagram @betterchicago.
Ravinia Food Truck Thursdays
Kicking off June 2 and running through September 8, the Ravinia Park District will be bringing back their community-loved Food Truck Thursdays. A splendid mix of food from local vendors and live music is sure to attract anyone looking to spend some time with the community this summer. Located at Jens Jensen Park from 4:30 to dusk — visit the Highland Park website for more information on food truck and musician line ups.
486 Roger Williams Ave., Highland Park
Prince: The Immersive Experience
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This interactive experience honors the purple-clad icon and his impact on the music industry. Transport yourself through 10 Prince-inspired spaces — like stepping into the classic Purple Rain album art — all of which celebrate his genius. The experience will run through August with tickets starting at $39.50, be sure to grab yours while you can!
540 N. Michigan Ave.
PAWS Days of Summer
Every Saturday this June PAWS Chicago will be having an adoption event. Each week’s events will be held at the Mariano’s in one of these four Chicago-adjacent towns: Skokie, Crystal Lake, Elmhurst and Lombard. Whether you’re picking out your new fuzzy friend or just going to soak up some cute-ness, be sure to stick around for the Goose Island beer tasting, too. Each event runs from noon to 3pm. Be sure to check out the PAWS website for specific locations and more information.
Highwood’s Evening Gourmet Market
With an incredible list of over 60 vendors supplying tasty food, drink and artisan items, the Highwood Evening Gourmet Market is sure to be just what you need for an evening out after a long day. Family-friendly, but also a good chance to leave the kids at home for a little adult fun, since the market runs 4:30 – 9:30pm every Wednesday, June 8 – August 22.
111 North Ave., Highwood
Ghost Army: The Combat Con Artists of World War II
If you have an interest in the history of our nation and its military operations, the Illinois Holocaust Museum and Education Center has a special exhibition that should intrigue you. This gallery recounts the tale of the top-secret U.S. Army’s 23rd Headquarters Special Troops, known as the “Ghost Army,” and their efforts which helped win the war. Artwork, uniforms, photographs and so much more will be on display for the public. The event runs through January, but you will want to catch it sooner rather than later.
9603 Woods Dr., Skokie
Jazzin’ at the Shedd
Starting June 15 and running every Wednesday through August, the Shedd Aquarium will be livening the South Loop up with its top-notch jazz ensembles. Their terrace, with stellar views of the skyline, will be reimagined into a space for drinks, mingling and the all-important jazz music — oh, and did we mention fireworks, too!
1200 S. DuSable Lake Shore Dr.
June 2: Pride & Prejudice: LGBTQ+ Voices Under Nazism
Join the Illinois Holocaust Museum & Education Center in commemorating the lives and stories of LGBTQ+ people following World War II, through their Online Lunch & Learn program. Learn about the truths and livelihoods of people that were erased from history and are now being brought into the spotlight to be preserved. The virtual event is free to the public and will take place at noon, more information and registration is available on the museum’s website.
June 3: We Can End Gun Violence Community Pop-Up Event
As the socio-political battle over gun safety continues, communities are doing their part to spread awareness and support for victims of gun violence. Join BUILD for a day of unity, featuring a community march — beginning at 3pm — followed by basketball, softball, music performances, games and more — all family-friendly. If you go, wear orange in support, as it is the color for National Gun Violence Awareness. More information can be found on BUILD’s site.
5101 W. Harrison St.
June 3 – 5: Do Division Street Fest
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Like many other festivals in the city, Do Division Street Fest has food vendors and live music — but did you know they will also have a family fun fest and fashion runway supported by local boutiques? An array of arts, entertainment and cuisine will be present at this year’s fest. Leashed dogs are welcome, too, making it a great outing for families!
2000-2200 W. Division St.
June 4: Highwood Pride Fest
The community of Highwood welcomes everyone to “show their Pride on the North Side” at the Highwood Pride Fest. Don’t expect run-of-the-mill celebrations either, this year they will have an all-ages “Werk the Runway” show; a Just Say Gay Drag Show; a “Taste the Rainbow” Pub Crawl; and much more. Events start at noon and run until the bars close. If you’re looking to celebrate your pride in the suburbs this June, look no further than this little slice of the North Shore, showing their love all month long.
June 4 – 5: Windy City Hot Dog Fest
If there is one thing Chicagoans know, it’s that hot dogs are a delicacy here. And the vendors at the inaugural Windy City Hot Dog Fest know that too, which is why some of the city’s best hot dog artisans are coming out for the droves of hungry attendees. From noon – 10pm each day catch some delicious dogs in Portage Park, while also acting as a judge for best dog and enjoying live, local music.
4000 N. Milwaukee Ave.
June 4 – 5: Street Art Fair
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After three years of absence, the 57th annual Street Art Fair is finally returning to the streets of Hyde Park. Collectors, artists and art lovers will all find something to enjoy at this fair that features nearly 150 artists — from leather making to glasswares — and is expected to bring in over 5,000 attendees. Whether you’re in the market to buy your next piece or just want a taste of culture, Hyde Park has what you need this summer. Hours vary per day, visit the fair’s website for specifics.
Downtown Hyde Park
June 5: Run for the Zoo
The Lincoln Park Zoo is bringing their 5k and 10k races back to the north side this year! No matter what distance you’re going, the scenic run will have you enjoying the fresh air this summer. There will also be a Kids’ Course for ages 3 – 8, and don’t forget to stop by the post-race celebration. If you’re looking to do something good for your body and interact with the natural world around us, this might just be the perfect fit. For start times, entry pricing and course logistics you can visit the LPZ website. And if you need help prepping, check out our guide to training for any race distance.
2001 N. Clark St.
June 5: Downtown Naperville Spring Wine Walk
Lovely downtown Naperville is waiting with open arms for you to stroll through local businesses tasting an array of wines — all of which goes to support Naperville Community Television. Have you been meaning to get some shopping done or looking for a chance to get together with friends? This evening will itch that scratch while also quenching your thirst. Previous years have sold out, so be sure to reserve your spot now. Registration is $50 and can be found on the Wine Walk’s page.
June 9 – 12: Summer ‘Grads & Grease’ Carnival
Calling all graduates! Highwood is bringing their Grads and Grease Carnival back for a second year with the promise of wholesome, Grease-themed summer fun. While the carnival is open for all, any 2022 graduate will receive discounted wristband prices for unlimited rides. And if you’re feeling the ‘50s theme, feel free to come decked out in costume — that will win you a discount as well! More information is available on the Highwood community website.
Downtown Highwood Metra Station Parking Lot
June 9 – 12: Chicago Blues Festival
The present, past and future of Blues music will be represented and celebrated at this year’s Chicago Blues Festival in both The Loop and throughout the city. Enjoy a lengthy line-up of musicians waiting to rock the city with shows playing all day long, featuring genres like soul, R&B and gospel. Admission is free.
Wells Street, between North Ave. and Division
June 10 – 12: Andersonville Midsommarfest
Though it took a two-year hiatus, the Andersonville Midsommarfest is back in full swing with a plethora of goodies such as 60+ music acts, diverse food vendors and even events for the kids. This Swedish tradition is in its 56th year here in the heart of Andersonville, and will do what it does best: highlighting all of the gems the neighborhood has to offer. Admission is a $10 donation, and hours of operation vary per day — visit the Andersonville Midsommarfest website for specifics.
5200-5520 N. Clark St.
June 11: Strides for Peace: Race Against Gun Violence
Join fellow runners in Grant Park for an 8k, 5k, 2-mile walk or Tots for Peace Sprint for kids — all for the awareness of gun violence in the city — sponsored by BUILD. Connect with community members; contribute funds if possible; and commit to the change necessary to end gun violence. More information can be found on BUILD’s website.
337 E. Randolph St.
June 11, 18, 25: Taste of Chicago
Come through on these three consecutive Saturdays to partake in one of Chicago’s favorite annual pop-ups: Taste of Chicago. This year, check out the daily 30 – 40 vendors who will be doing what they do best in neighborhoods across the city, as well as a line up of musicians at the Grant Park location. Admission prices vary, visit the Taste of Chicago page for specifics.
June 12: Summer Family Festival
Parents, if you’re looking for an all-out experience for your kiddos look no further than the Summer Family Festival hosted by the Kohl Children’s Museum. With a loaded schedule — including a petting farm, butterfly tent, children’s music concert and even a meet and greet with Tinkerbell — your kids will no doubt find the kind of summertime fun they are jonesing for. The event runs from 2:30 – 5pm and tickets can be purchased on the Kohl Children’s Museum website.
2100 Patriot Blvd., Glenview
June 12: The Hampton Social: The Pink Party
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If you like rosé, you’re going to love The Pink Party at Chicago’s chic restaurant The Hampton Social. From noon to 6pm, enjoy sampling rosé, gourmet bites and even a guest appearance and DJ set from Brody Jenner and Devin Lucien. This classy shindig will have you and your friends buzzing. For more specifics and to grab your tickets, visit The Hampton Social event page.
1603 North Lake Shore Dr.
June 18: Black Panther in Concert
This multi-sensory evening is sure to excite lovers of the Marvel classic Black Panther. Join the Chicago Philharmonic Society as they perform the award-winning score in time with a screening of the film. The evening begins at 7:30pm and tickets start at $49.50 — registration and additional information can be found on the Chicago Philharmonic Society website.
175 N. State St.
June 18 – 19: Artists of the Wall Festival
This interactive experience is suited for any artist — whether your skills are unmatched or you only dabble in your medium. Located by the Loyola Beach, the “wall” is awaiting a stroke of genius from local artists. Be sure to reserve your spot, as there is a finite amount of space on the wall. This year’s theme — selected from among 30 ideas — is “World of Tomorrow,” so get to your tools and start brainstorming. More information is available on the Loyola Park website.
1230 W. Greenleaf Ave.
June 18 – 19: Gold Coast Art Fair
With an extensive list of 200 multi-medium artists, this art fair will wow almost any attendee — and so will the delicious food, too! Held in Grant Park’s Butler Field, the fair’s convenient location at the heart of the city should have locals and tourists alike flocking to it — from 10am – 5pm Saturday and Sunday.
South Lake Shore Dr. and E. Monroe St.
June 19: Festival on the Square
Head over to the Congo Square Theatre to be one of the many people sharing in art, live music, theatrical readings and so much more in celebration of Juneteenth. There will also be a 10-Minute Play Festival Competition in which the 2022 Samuel G. Roberson Next Up Fellowship winner will be announced. Come share in the uplifting joy, beginning at 1pm. Registration can be found on the Congo Square Theatre website.
1016 N. Dearborn St.
June 19: Thank You Chicago Juneteenth Market
The Promontory in Hyde Park is the spot to be for this market showcasing black-owned businesses. The indoor and outdoor market will have vendors showcasing fashion, food, beauty goods for the public to peruse. The market will run from 2pm – 7pm, admission is free.
5311 S. Lake Park Ave.
June 19th: Father’s Day Weekend Sunset Cruise
If you want to celebrate Dad the way he deserves, come aboard the Father’s Day Weekend Sunset Cruise. Enjoy beautiful views of Lake Michigan, music and a full bar of tasty beverages. Leave the little ones at home, however, since this event is 21+. For regulations, registration and more information visit the Father’s Day Cruise website.
DuSable Harbor, 200 N. Breakwater Access
June 19: YWCA’s Race Against Hate
Each year, the Race Against Hate brings together thousands of people from all over Chicagoland to run and walk in unity against racial hatred and violence. Proceeds from the Race Against Hate are used to further the mission of YWCA Evanston/North Shore, in particular their efforts in the areas of racial justice and violence prevention. Sign up online.
June 23: Adults Night Out: Pride Party!
Want to get out of the house for the night and into a little fresh air? Well if Pride celebrations are your thing, this night out at the Lincoln Park Zoo is calling your name. Enjoy sipping and strolling through the grounds from 6:30 – 10pm, as well as Drag Queen Bingo, DJ sets from LGBTQIA+ artists, lawn games and even take a spin on the AT&T Endangered Species Carousel. When you look back on 2022’s Pride Month, this night is sure to be one to remember. Tickets start at $15 for early birds, so grab your tickets while they’re hot.
2001 N. Clark St.
June 24 – 25: Taste of Highland Park
The atmosphere at the inaugural Taste of Highland Park is sure to delight passersby — as the aromas from delicious, local food and sounds of top-notch musicians bring the community together. Enthusiasts in the kitchen may also want to catch some of the cooking demos offered at the fest, too. Family- and community-friendly, more information can be found on the Highland Park homepage.
The Lot, 523 Central Ave., Highland Park
June 25 – 26: Pride in the Park
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Chicagoans know that with June comes Pride in the Park — the annual music, dance festival dedicated to LGBTQIA+ artists. Held in Grant Park, this two day, all-out experience is a great excuse to dance your heart out and revel in the city’s energy. More information and tickets are available on the Pride in the Park website.
June 26: Chicago Pride Parade
For the LGBTQIA+ community of Chicago, the event of the year is back and as vibrant as ever. The 51st annual Pride Parade will make its way from Uptown, through Northalsted — formerly Boystown — and end in Lincoln Park, from noon – 3pm. So grab your friends and your flags and hit the streets to show a little Pride this summer.
June 26: Evanston Garden Walk
Wind your way through the beautiful neighborhoods of Evanston and marvel at the eight private and church garden spaces the tour will visit. The gardens are each unique enough to attract a wide-range of attendees. And if you need another reason to join in the splendor, all proceeds go to the Evanston Environmental Association which supports local students and wildlife. Tickets are on sale now, and prices will vary as the event gets closer — more information can be found on the Garden Walk’s website.
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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.