CHICAGO — Pumpkin spice season is near, but there are still plenty of things to do in the city before the cooler months settle in.
Chicago’s legendary Jazz Festival takes place this weekend, as well as ARC Music Festival, Taste Of Polonia, the African Festival of the Arts, WingOut Chicago, Bike the Drive with Team Envision, Afro Fusion Pop-Up, Healing Arts Chicago Summit and Books and Beer at Turner Haus Brewery.
You can also walk solo or with friends for Hot Girl Walk at Lincoln Monument Gardens or adopt a new furry friend at Pup Social’s Adopt and Shop.
Here are 26 things to do this weekend in Chicago:
All Weekend
Chicago Jazz Festival
6:30–9 p.m. Thursday, 4-9 p.m. Friday-Sunday
Millennium Park, 201 E. Randolph St.
Enjoy world-renowned headlining performers as well as local musical treasures at Chicago’s legendary free Jazz Festival, now in its 56th year. Headliners include boundary-pushing bassist and vocalist esperanza spalding, piano legend Monty Alexander, trumpeter and vocalist Kermit Ruffins, Afro-Cuban guitar virtuoso Eliades Ochoa of Buena Vista Social Club and saxophonist Gary Bartz.
More info is here.
ARC Music Festival
2-10 p.m. Friday-Sunday
Union Park, 1501 W. Randolph St.
Only Friday passes remain for the ARC Music Festival, Chicago’s high-energy fest of house and techno music in Union Park. ARC returns for its fifth year to celebrate Chicago as the birthplace of house music, “reconnecting house with its Black, queer, and underground roots, and introducing a new generation of listeners to its foundational story.” Friday’s performers include Jamie XX, Adriatique, DJ Tennis, Eric Prydz, Hot Since 82 and Amelie Lens.
Single-day passes start at $189; more info is here.
Taste of Polonia
4:30-10:30 p.m. Friday, 11:30 a.m.-10:30 p.m. Saturday-Sunday, 11:30 a.m.-9:30 p.m. Monday
Copernicus Center, 5216 W. Lawrence Ave.
The Taste of Polonia Fest also returns this weekend, the largest Polish festival in the country. Enjoy Polish food and drink as well as dance performances, live music, exhibitions, tastings, movie screenings, local vendors and of course a kids’ zone (with bounce house). Tickets start at $10, with $45 for a four-day pass.
More info and tickets here.
African Festival of the Arts
10 a.m.-10 p.m. Saturday-Monday
Washington Park’s Sunken Gardens, 5500 S. Cottage Grove Ave.
The African Festival of the Arts, now in its 35th year, not only offers an astounding array of local visual artwork, but also a full weekend of live music and entertainment, capped off by this year’s headliners, legendary R&B group the S.O.S. Band.
Tickets start at $25, with family passes available for $60. More info here.
WingOut Chicago
1:30-8:30 p.m. Saturday, 1:30-7:30 p.m. Sunday
Gallagher Way, 3635 N. Clark St.
Wings fans should run, not walk, to the 10th annual WingOut Chicago outside Wrigley Field, featuring the finest providers of wings from all over the city. Alongside wing sampling, you’ll also enjoy live music, adult beverages, competitions and more. Vendors include Smoke Daddy, Hangry’s, Parlay at Lincoln Park, Rizzo’s Bar & Inn, New Line Tavern, Yak-Zies, Metro Wings and many more. General admission tickets are $25; VIP options are sold out.
More info here.
32nd Annual Fiesta Boricua
Noon-9 p.m. Saturday-Sunday
Division Street between California and Western avenues
Enjoy a weekend celebrating Puerto Rican culture in Chicago at Fiesta Boricua this weekend. The festival will have live musical performances from acts like Las Bompleneras and Jussie Reyes, a fashion show curated by Ya Ready!, Puerto Rican food and more.
This event is free and open to the public. Learn more about the event here.
Gladiator Fright Night
Various times Friday-Sunday
Bramble Arts Loft, 5545 N. Clark St.
Gladiator Fright Night will happen at the Bramble Arts Loft all weekend. Enjoy this immersive theatrical fight show where horror icons face off in a battle for victory. There will be scares, laughs and (fake) blood.
General admission starts at $25.31 for all weekend shows, with a limited number of industry tickets available. Learn more about the show and ticket prices here.
Friday
Fuel The Bloc Party with Vic Mensa
4-7 p.m. Friday
BLOC Dispensary, 3545 N. Kedzie Ave.
BLOC Dispensary will host the Fuel the Bloc Party, featuring a live DJ set from Vic Mensa alongside local vendors, food and music. Attendees can also get two free tacos from Naty’s Tacos with every purchase from BLOC.
General admission is free, and the event is on a first-come, first-served basis. Learn more about the event and lineup here.
TPP and Saturn & Jupiter Collab Open Mic
6:30-11 p.m. Friday
The.BlkRoom, 4015 W. Carroll Ave.
The People’s Party and Saturn and Jupiter are hosting an open mic for participants interested in speaking what is on their mind. There will also be live music from DJ John West and a denim drive, as well as a writing session.
Tickets are on a pay-what-you-can scale. Learn more about the event here.
Call and Response August Trivia Night
7-8:30 p.m. Friday
Call and Response Books, 1390 E. Hyde Park Blvd.
Join Call and Response for their monthly Trivia Night. Come in a team or alone and make new friends. Trivia questions will cover a variety of topics, with some “bookish” questions included. Attendees are welcome to bring snacks and beverages, and the event is open to all ages.
The trivia night is free and open to the public. Learn more about the event here.
Saturday
St. Richard Catholic Church’s Art & Craft Fair Summer Market
9 a.m.-5 p.m. Saturday
St. Richard Catholic Church, 5032 S. Kostner Ave.
St Richard Church will host its Art and Craft Summer Market. The market will have over 50 local vendors selling food (including Thai, Mexican, baked goods and candy), jewelry, clothing, face painting and more. There will be two live dance performances from folkloric dance groups.
Admission to the event is free. Learn more here.
Hot Girl Walk Chicago
9:30-11:30 a.m. Saturday
Lincoln Monument Gardens, 1650 N. Dearborn St.
Go solo and make new friends or with your current girl group at Hot Girl Walk, a monthly community walk designed to help you get your steps in and get your groove back. This TikTok famous walk returns to Chicago this weekend hosted by creator and founder, Mia Lind, and led by Hot Girl Walk Ambassador, Kylie. Hot Girl Walk is open to all ages and genders, and there will also be giveaways for attendees, including an HGW bandana.
The event is free and open to the public. Learn more here.
2025 Healing Arts Chicago: An Arts x Health x Wellness Summit
10 a.m.-3 p.m. Saturday
Malcolm X College, 1900 W. Jackson Blvd.
Healing Arts Chicago will return to Malcolm X College for its Healing Arts Chicago Summit. This summit brings healing-centered, artist-led programs to clinics and communities across the city and will feature art making, workshops, performances and more. Sessions include topics like “Once Upon a Pose Fairy Tale Yoga,” a sound bath meditation and a collaborative mural.
Admission to this event is free to the public with registration. Learn more here.
Paving The Way Project Inc. 10th Annual Summer Cool Down
11 a.m.-4:30 p.m. Saturday
5025 S. State St.
Paving The Way Project Inc. will host its 10th annual Summer Cool Down, a day filled with cooling off and beating the heat. The cool down will have games, music and food and provide the space to be in community.
Admission to this event is free. Learn more about the event here.
Summer Brunch Saturdays at Miyagi Records
11 a.m.-5 p.m. Saturday
Miyagi Records, 307 E. Garfield Blvd.
Miyagi Records will host its last Summer Brunch Saturday of the year with K-Tex BBQ. The Summer Brunch Saturdays series focuses on bringing together the store’s favorite local food pop-ups, good coffee, drinks and the right soundtrack.
The event is free and open to the public on a first-come, first-served basis. Learn more about the event here.
End of Summer Clothing Swap
Noon-2 p.m. Saturday
Chicago Public Library Uptown Branch, 929 W. Buena Ave.
The Uptown Chicago Public Library Branch will host a free clothing swap organized by three friends living in the neighborhood. All are welcome, even if you have nothing to bring to the swap. Remaining clothes will be donated to Brown Elephant.
Admission to this event is free. Learn more here.
Pup Social’s Adopt and Shop
Noon-6 p.m. Saturday
Pup Social, 2200 N. Ashland Ave.
Join Pup Social for its first Offleash Bar and Park. The event will bring local rescues and a curated pet-themed market with accessories for pets including specialized natural dog treats to wellness essentials.
There will also be refreshments for pet owners and drink sampling, including Maplewood Brewing tastings and Ghost energy drinks. All ticket purchases include access to the market and adoptable puppies, a $5 drink voucher, special raffle prices and photo ops.
General admission tickets start at $22.11. Learn more about the event and ticket prices here.
Bronzeville Strong Towns Pop-Up at Overton
1:30-5:30 p.m. Saturday
4927 S. Indiana Ave.
Join Strong Towns Chicago, Creative Grounds, Borderless Studio and neighbors for a community day at Overton. The event will have collaborative projects and creative activities for all ages to participate in as you learn more about Strong Towns, a local group that advocates for policies to make neighborhoods more affordable, streets safer and the city easier to navigate. There will also be refreshments provided.
Admission to this event is free. Learn more here.
CareFreeBlackGirl Cookout Chicago
2-8 p.m. Saturday
Park No. 540, 2401 S. Federal St.
CareFreeBlackGirl will host an interactive day event for Black women and femmes in the city. The cookout will have live performances from Black women DJs, entertainers and hosts, vendors of all kinds, creative activities and more.
Attendees are encouraged to bring a blanket or chair, wear comfortable clothes and to enjoy all the activities and goodies that happen throughout the day.
Admission tiers with varying perks for each tier. “Girl” tickets start at $12.51 for entry and activities, and “Black” tickets start at $23.18 that includes entry and activites along with a swag bag. Learn more about the event and ticket prices here.
Black Girl Field Day
3-7 p.m. Saturday
Fulton Market, 800 W. Fulton Market
Embrace your inner child with Black Women In Color for their Black Girl Field Day. The field day will have adult-style field games, an outdoor movie, outdoor lounge, complimentary wellness juice samples and a chance to learn how to play pickleball.
Early-bird general admission tickets start at $65.87, and Early-bird ‘My Bestie and Me’ tickets start at $119.82. Early-bird general admission tickets plus 1-month BWIC membership start at $65.87. Learn more about the event and ticket prices here.
RISE + Shine Performance Arts Showcase and Open Mic
6-8 p.m. Saturday
RISE Dispensary, 1357 N. Elston Ave. Suite #155
RISE + Shine will hold a space for creativity and expression at RISE Dispensary. The event will feature a night of performances by Chicago’s overlooked talents. The lineup includes Amir Tripp, Mara Love, Saenovia Poole, Kiemofwheat and Schenay Mosley.
General admission tickets are split into tiers. The first tier tickets start at $23.18, and the second tier tickets start at $28.52. VIP Couch section tickets start at $39.19. Ticket discounts are available as well. Learn more about the event and ticket prices here.
Sunday
Bike the Drive with Team Envision
6:30-11 a.m. Sunday
235 S. Columbus Drive
Bike down DuSable Lake Shore Drive this weekend with Team Envision for their 24th annual Bike the Drive. The trail is opened exclusively for all bikes and bikers of all abilities. Attendees have the choice to ride a bike from Envision Unlimited or are welcome to bring their own.
This event is free and open to the public. Learn more here.
Queens In The City Picnic
1-5 p.m. Sunday
3858 S. Cottage Grove Ave.
Queens Academy will host its Queens In The City Picnic to celebrate womanhood and sisterhood. The picnic will have food and beverages, live DJ, special performances, local vendors, giveaways and more. Good vibes only: Wear yellow so that the whole crowd will glow together!
General admission tickets start at $23.18. Learn more about the event and ticket prices here.
Books and Beer
2-5 p.m. Sunday
Turner Häus Brewery, 78 E. 47th St.
Find your next read, enjoy a nice cold beer and shop local this weekend at Turner Häus Brewery. The brewery will collaborate with Da Book Joint to host a pop-up book fair for book and beer lovers alike.
The event is free and open to the public. Learn more about the event here.
HIgh Vibes Chicago Festival
2-8 p.m. Sunday
Village Bucktown Dispensary, 1850 W. Webster Ave.
In the mood for 420 fun? This weekend’s High Vibes Chicago Festival will feature live music, local food and art vendors, brand pop-ups and more for all.
General admission tickets start at $12.51. Learn more about the event and ticket prices here.
Afro Fusion Pop-Up Edition
11 p.m. Sunday-4 a.m. Monday
Le Nocturne Chicago, 4810 N. Broadway
Afro Fusion will host a Labor Day pop-up party featuring DJs who are masters at blending genres ranging from hip-hop, R&B, reggae, Afrobeats and more.
Early Bird tickets start at $12.51, and discount entry tickets start at $23.18. General admission tickets start at $28.52, and table reservations start at $55.20. Learn more about the event and ticket prices here.
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