28 Things To Do In Chicago This Weekend: Pride Fest, Juneteenth And Obama Center Open House

CHICAGO — Hyde Park is welcoming the Obama Presidential Center to the neighborhood with the museum’s grand opening.
The Obama Center is hosting a weekend-long open house where families are invited to explore the grounds while enjoying live performances, art workshops, family activities and more.
Pride Fest, a celebration of Chicago’s LGBTQ+ community and pride, is also this weekend in Northalsted. And Juneteenth events are planned in neighborhoods across the city. Find a full list of Juneteenth events here.
Here’s a roundup of 28 things to do in Chicago this weekend:
All Weekend
Taste of Randolph festival in West Loop in 2025. Credit: Facebook
Taste Of Randolph
5-10 p.m. Friday, noon-10 p.m. Saturday-Sunday
900 W. Randolph St., West Loop
Taste of Randolph is returning for another summer of food and music in the West Loop. Featuring local restaurants like Nia and Mac’s Deli, there is plenty of food to explore while enjoying a wide lineup of live music all weekend long across two stages. There’s also a kid zone, a vendor market and more.
This is a free event. Learn more here.
Former President Barack Obama greets children playing on the playground at the Obama Presidential Center on June 13, 2026. Credit: The Obama Foundation
Obama Center Open House Event
10:30 a.m.-3 p.m. Friday, 10 a.m.-5 p.m. Saturday-Sunday
The Obama Presidential Center, 6001 S. Stony Island Ave., Hyde Park
Even though tickets are sold out for the museum’s for the grand opening weekend of the Obama Presidential Center, families can still explore the Hyde Park campus and all it has to offer for free all weekend. There will be live music, interactive art workshops like button-making and screen-printing, plus sports clinics with Chicago teams and more.
This is a free event. Learn more and find the weekend schedule here.
Blacks in Green founder Naomi Davis and consultant Asadah Kirkland stand outside of the Green Living Room community gathering space in 2019. The nonprofit will open the Woodlawn and South Lakefront Tourism Center in the same building this weekend. Credit: Katie Pyzyk/Block Club Chicago
Woodlawn Bike, Walk & Culinary Tours
Various times Friday-Sunday
The Woodlawn & South Lakefront Tourism Center, 6431 S. Cottage Grove Ave., Woodlawn
Blacks in Green, a South Side environmental nonprofit, is soft-launching its tourism center this weekend with walking, biking and bus tours. Stops will include Blacks in Green developments and gardens, while bike tours will take guests on an 8-mile ride through the South Side focused on the Till family history and the Great Migration. Culinary tours will include visits to the Bronzeville winery and more.
Read more about Blacks in Green’s new development here.
Tickets are $45 for the biking tour, $50 for the walking tour and $70 for the culinary tour. Learn more and buy tickets here.
Credit: Facebook
Fiesta Back Of The Yards
Various times Friday-Sunday
Ashland Avenue from 45th to 47th streets, Back of the Yards
This three-day street festival brings live entertainment, carnival rides, Latin cuisine and games to Back of the Yards to showcase the culture and history of the neighborhood.
Tickets start at $75 for a three-day wristband for unlimited rides. Learn more and buy tickets here.
Credit: Facebook
Gold Coast Art Fair
10 a.m.-5 p.m. Saturday-Sunday
Grant Park Butler Field, South DuSable Lake Shore Drive and East Monroe Street, The Loop
Featuring over 200 juried artists, the Gold Coast Art Fair is back for its 68th year. Head to Grant Park to explore the wide lineup of artists as they display their paintings, sculptures, jewelry, ceramics and more. There will also be painting classes, henna art, caricatures and a Kid Art Zone.
Tickets are $10 if bought prior to the event, $15 at the door and free for children younger than 12. Learn more and buy tickets here.
Mister Wallace & Friends performs at Planet Peach, a colorful, queer Juneteenth pride celebration that occured at Pride Fest on June 19, 2022. The two-day festival happens the weekend before the Chicago Pride Parade. Credit: Kathleen Hinkel/Block Club Chicago
Pride Fest
Saturday and Sunday
Halsted Street from Addison to Grace streets, Northalsted
Held every year the weekend before the Chicago Pride Parade, Pride Fest is a two-day street festival and celebration. Enjoy live performances across three stages, like a Pride Fest drag show, appearances from the Chicago Gay Men’s Chorus and live music from artists DJ Ca$h Era, G Flip and more. There will also be a Youth Pride Space, a Proud Pet Parade, endless food vendors and more.
There is a suggested $20 donation upon entry. Learn more here.
A previous Chicago Food Truck Festival. Credit: Instagram
Chicago Food Truck Festival
Saturday and Sunday
2300 S. Indiana Ave., Near South Side
The Chicago Food Truck Festival is back for Season 13, featuring a lineup of chef-prepared plates from Chicago’s best food trucks and margaritas in a variety of summer flavors from the Daisy Margarita collection.
Tickets are free and $12.51 for VIP admission. Learn more and buy tickets here.
Thursday
Pride Bingo
6 p.m. Thursday
Elston Electric, 1357 N. Elston Ave., Bucktown
Come play bingo at Elston Electric as the monthly series that raises funds for nonprofits returns. This month, attendees will support LIFE IS WORK, a trans-led organization that works to educate, empower and organize LGBTQ+ people. Arrive early to snag your bingo sheet and a space, then compete in 10 rounds of play for a chance to win prizes like an LED Malort sign, a pair of tickets to Empty Bottle and more.
Learn more here.
Department of Cultural Affairs and Special Events hosts live music at the annual Millennium Park Summer Music Series on the Pritzker Stage. Shown: A previous DCASE event in July 2025. Credit: Walter Mitchell
Millennium Park Summer Music Series
6:30 p.m. Thursday
Jay Pritzker Pavilion, 201 E. Randolph St., The Loop
Celebrate Juneteenth with the Millennium Park Summer Music Series as organizers welcome Black chamber music collective D-Composed and Kahil El’Zabar’s Ethnic Heritage Ensemble. Special guests Nona Hendryx and David Murray will also take the stage for “Let The Spirit Out!,” the series’ official Juneteenth celebration.
This is a free event. Learn more here.
Friday
Credit: Instagram
Freedom 5K
8:30 a.m. Friday
Burnham Park, 39th Street and West Pershing Road, Oakland
Run, walk or jog the Freedom 5K in a celebration of Juneteenth and as a tribute to Lincoln Pettaway, an activist, educator and historian. All are welcome to the 5K, including those walking or with running strollers. ShoMO Fitness encourages you to not worry about pace, but to finish strong.
Learn more and register for $75 here.
Credit: Instagram
Mike Weary Solo Exhibition
6-9 p.m. Friday
Gallery Guichard, 436 E. 47th St., Bronzeville
Artist Mike Weary from Baton Rouge, Louisiana, is headed to Bronzeville to open his exhibit, “The Will to Escape.” The painter explores grief and inherited trauma while depicting the American South, where “Black bodies are pressured to shed personhood to survive.”
This is a free event. Learn more and reserve a spot here.
Bridgeport Art Center Third Friday Open Studios
7-10 p.m. Friday
Bridgeport Art Center, 1200 W. 35th St., Bridgeport
The Bridgeport Art Center will have its 14th annual Juried Art Competition, which showcases Chicago-area artists. Browse the artists’ unfinished works or enjoy a selection of original pieces for sale as artists debut “Canvas, Color & Vision,” an exploration of abstract and surrealist art.
This is a free event. Learn more and reserve a spot here.
Old Town School of Folk Music, 4544 N. Lincoln Ave. Credit: Facebook
Old Town School Of Music Juneteenth Celebration
7:30 p.m. Friday
Old Town School of Folk Music, 4544 N. Lincoln Ave., Lincoln Square
Immerse yourself in Chicago blues as the Old Town School of Folk Music celebrates Juneteenth with a special performance featuring the Freddie Dixon Blues Band and violinist Judy Lei.
This is a free event with a suggested donation. Learn more and reserve tickets here.
Saturday
10-11:30 a.m. Saturday
Elm Park, 5215 S. Woodlawn Ave., Hyde Park
Kick off Saturday morning with your Hyde Park neighbors as Trash People heads to the neighborhood for another community cleanup. The group spends about an hour picking up trash while beautifying Chicago neighborhoods.
This is a free event. Registration is required. Learn more and register here.
A previous Artecito workshop in Pilsen. Credit: Facebook
Kinetic Art Workshop
10 a.m.-1 p.m. Saturday
Blue Door Neighborhood Center, 2551 W. Cermak Ave., Pilsen
Children and families can learn more about the axolotl, a species of mole salamander, with the Lincoln Park Zoo and OPEN Center for the Arts. The free workshop series uses art to engage families with nature, and the event will include a related art activity to encourage families to think about their relationship to nature in creative ways.
This is a free event, and all materials will be provided. Learn more here.
Credit: Facebook
Be My Neighbor Day
10 a.m.-2 p.m. Saturday
Kosciuszko Park, 2732 N. Avers Ave., Logan Square
Join WTTW for the ultimate Be My Neighbor Day celebration with a live performance from the Chicago Children’s Theatre, ballet lessons, a soccer clinic and more. Plus, Daniel Tiger and Donkey Hodie will make an appearance alongside plenty of other free family activities.
This is a free event. Learn more and register here.
Neighbors selling goods at the Bernard Street Yard Sale. Credit: Courtesy of Mark Raulston
Bernard Street Sale
10 a.m.-3 p.m. Saturday
North Bernard Street between Fullerton and Wrightwood avenues, Logan Square
A neighborhood tradition for more than 46 years, the Bernard Street Sale is back this Saturday. Stroll Bernard Street as 37 houses on the blocks set up shop for a mega yard sale.
This is a free event. Learn more here.
Credit: Facebook
6th Annual Bronzeville Juneteenth Celebration
10 a.m.-3 p.m. Saturday
Absolutely Anything Essential, 3521 S. King Drive, Bronzeville
Celebrate Juneteenth in Bronzeville as the neighborhood hosts its sixth annual Juneteenth community celebration. Building on last year’s theme of “Honoring the Legacy of Freedom,” the festival will celebrate culture, resilience and the power of living life fully. There will be live performances and entertainment, local vendors, family-friendly activities, plus a special recognition of fathers and father figures for Father’s Day.
This is a free event. Learn more here.
1880s Black Founders Bike Tour
10:45 a.m., 1 p.m. Saturday
610 E. 111th St., Pullman
Rediscover and honor the stories of three Black founding families in Pullman as the Historic Pullman Empowerment Organization take 15 bicyclists through the Far South Side neighborhood. The 3-mile bike ride will showcase African-American workers and families who lived in the north end of Pullman during the 1880s and 1890s.
This is a free event. Learn more and reserve a spot here.
Credit: Instagram
Englewood Book Fest
11 a.m.-4 p.m. Saturday
6234 S. Wolcott Ave., Englewood
Join the Englewood Summer Book Fest, hosted by Wood St. Collective, and enjoy book giveaways, poetry, panel discussions, interactive experiences and more. There will be face painting and food for all. This event is meant for all ages, and it serves to bring books, arts, performances and more to over 600 local families.
This is a free event. Learn more here.
Credit: Facebook
Peruvian Arts And Cultural Festival
1 p.m. Saturday
Blackhawk Park, 2318 N. Lavergne Ave., Cragin
The Center of Peruvian Art is kicking off its summer festival series Saturday. In collaboration with the Park District’s Night Out in the Parks series, you can enjoy a Peruvian dance workshop, an instrument workshop, live music, traditional dancing, authentic food and more.
This is a free event with installments throughout the summer. Learn more here.
A previous meetup of the Oak Street Beach Jugglers. Credit: Facebook
World Juggling Day
1-10 p.m. Saturday
1301 N. Lake Shore Drive, Gold Coast
June 20 marks World Juggling Day, and the Oak Street Beach Jugglers are celebrating with a full day of juggling and more activities. Stop by for free lessons, refreshments, exhibitions and more, plus enjoy extra props to try it out yourself.
This is a free event. Learn more here.
Credit: Provided
The Belonging Bash
2 p.m.-midnight Saturday
Collaboraction Theatre, 1757 N. Kimball Ave., Humboldt Park
Support the Light Summer Youth Program and the House of Belonging as Collaboraction Theater puts on its Belonging Bash, an indoor-outdoor block party. Enjoy performances, food and activities all day, then head inside for live comedy, DJs and more live music. Catch performances from Larry Miller, the Light, the Corey Wilkes Quartet and more.
Tickets start at $25. Learn more and buy tickets here.
The Northcenter Town Square in Chicago’s North Center neighborhood on Dec. 3, 2020. Credit: Colin Boyle/Block Club Chicago
Chicago After Dark: Northcenter
3-9 p.m. Saturday
Northcenter Town Square, 4108 N. Damen Ave., North Center
Head to the Northcenter Town Square for a free evening of arts, food and drink, performances and more. There will be vendors and activities for the entire family.
This is a free event. Learn more here.
Credit: Instagram
Medieval Midsommar Faire
3-9 p.m. Saturday
Sideshow Gallery, 2219 N. Western Ave., Bucktown
Lovers of the mystical can stop by Sideshow Gallery’s Medieval Midsommar faire as the curiosity shop transforms its courtyard garden into the ultimate folk vendor market. You can browse handmade heritage crafts and enjoy offerings from mystics like fortune telling and tarot.
This is a free event. Learn more here.
Credit: Instagram
Boots: Pride Edition
10 p.m. Saturday
Metro/SmartBar, 3730 N. Clark St., Wrigleyville
Created by DJ Kirk and drag performer Abhijeet, Boots is back for a full-building Pride party at Metro/SmartBar. Catch DJ sets from artists such as Prosperity Room and Daru, while hosts Ash Wednesday, Allura The Doll and more bring even more energy to the Pride party. Don’t forget to take a peak at the art installations by JForPay and Pagina.
Tickets start at $25. Learn more and buy tickets here.
Sunday
Nejla Yatkin will be hosting a Summer Solstice sunrise meetup on Sunday morning. Credit: Facebook
Summer Solstice Summer Sunrise Movement Gathering
5:30 a.m. Sunday
Theater on the Lake, 2401 N. DuSable Lake Shore Drive, Lincoln Park
Sunday marks the Summer Solstice and choreographer Nejla Yatkin is welcoming the longest day of the year with a morning beach walk, breath work and sun salutations. Watch the sunrise while taking time to pause and celebrate nature and summer.
This is a pay-what-you-can event. Learn more and RSVP here.
Credit: Instagram
Pride Beach Sit
9 a.m-1 p.m. Sunday
Rainbow Beach Park, 3111 E. 77th St., South Shore
Chicago BIPOC Birders invites queer and trans BIPOC birders and their families for a morning of birding at Rainbow Beach. Explore the diverse patterns of gender and sexuality in birds as participants reflect their own experiences as humans. Bring a blanket or folding chair, and BIPOC Birders will provide snacks and loaner binoculars.
This is a free event. Learn more and reserve a spot here.




