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23 Things To Do In Chicago This Weekend: Labor Day Parades, ARC Music Festival, Bike The Drive And More

The Chicago Jazz Festival, Taste Of Polonia, Fiesta Boricua and rescheduled Queer Fam Pride Jam are also on tap.

Over 16,500 bikers attended Bike the Drive in 2022.

CHICAGO — Neighbors can march with Labor Day parades, kick off Hispanic Heritage Month with karaoke, groove to Chicago Jazz Festival performances, attend the country’s biggest Polish festival and much more this holiday weekend.

Here’s a roundup of 23 things to do in Chicago this weekend:

Chicago Labor Day Parade & Eddie Fest

Noon-6 p.m. Saturday

108th Street and Cottage Grove Avenue, marching south to 113th Street

This year’s Chicago Labor Day Parade is making its way to the Pullman Historic District for the first time. Afterwards, celebrate workers and the labor movement with music, food and family-friendly activities at Eddie Fest, named for the late labor activist Ed Sadlowski.

West Loop Art Fest

10 a.m.-7 p.m. Saturday-Sunday

At West Fulton and North Sangamon Streets

Stroll through four blocks of art that will be on display and available for purchase in the heart of West Loop. There will also be wine tastings, children’s crafts and live music at this family-friendly fest.

Chicago Jazz Festival

11 a.m.-9 p.m. Thursday, 11:30 a.m.-9 p.m. Friday, 11 a.m.-9 p.m. Saturday and Sunday

Millennium Park — Jay Pritzker Pavilion, 201 E. Randolph St. and other locations

Catch free jazz performances by local, national and global talents to celebrate one of Chicago’s most beloved art forms. There will also be performances at venues across the city, including the Chicago Cultural Center, the Harris Theater Rooftop and the South Promenade Listening Lounge. Find the full performance line-up and learn more about the fest here.

Credit: Colin Boyle/Block Club Chicago
Fans dance as Nicole Moudaber performs at the The Grid stage during the premier day of Arc Music Festival in Union Park on Sept. 4, 2021.

ARC Music Festival

Kicks off 1 p.m. Friday-Sunday

Union Park, 1501 W. Randolph St.

ARC Music Festival is Chicago’s flagship house and techno festival, and it’s bringing internationally renowned talents to the birthplace of house music this weekend. Check out Sweden’s Adam Beyer, England’s Fatboy Slim, Ukraine’s Miss Monique and more than 70 other musicians. Find the full line-up here. A variety of single-day tickets and weekend packages are available online.

Taste Of Polonia

5-10 p.m. Friday, noon-8 p.m. Saturday, 11 a.m.-6:15 p.m. Sunday, noon-6 p.m. Monday

Copernicus Center, 5216 W. Lawrence Ave.

Check out the nation’s largest Polish festival this weekend, complete with live music, dance performances, authentic Polish food, local merchants, a casino, beer garden, family-friendly activities and more. Find the full schedule online. One-day passes for $10-15 and weekend-long passes for $45 are available here.

Fiesta Boricua

Noon-8 p.m. Saturday and Sunday

Division Street between Western Avenue and California

A celebration of Puerto Rican culture, the 30th annual fest is one of the largest of the Latino community in the Midwest, attracting more than 200,000 people annually, organizers said. It will feature music — from bomba and plena to salsa, merengue, folk music and hip hop — performances, boxing lessons and vendors from all over Chicago and Puerto Rico. Free.

WOOGMS Labor Day Parade

11 a.m. Monday

Corner of Pine Grove and Wellington Avenues in Lakeview

Everyone gets to march in this “Do-It-Yourself” Labor Day Parade. A Lakeview tradition hosted by The Wellington Oakdale Old Glory Marching Society (WOOGMS), neighbors (and pets) from across the city are invited to march, bike and scooter along with the crowd. There will also be a performance by the Jesse White Tumblers.

Credit: Provided/Ama Merrell Photography
The Queer Fam Pride Jam team posed for a photo before the festival was ultimately rescheduled.

Queer Fam Pride Jam

10 a.m.-3 p.m. Saturday

The Salt Shed, 1357 N. Elston Ave.

This free, family-friendly Pride event celebrates being “Queer all year.” It features a food and maker market, plus entertainment activities for all ages. There will be art making, family yoga, a sing-along, skateboarding, drag makeovers and performances, house music dance lessons and more. The event was rescheduled from its original June 17 date. You can RSVP here.

Live @ Lighthouse Summer Jazz Concert

7 p.m. Thursday

Lighthouse Artspace, 108 W. Germania Pl.

Catch Lighthouse Artspace’s final summer concert this weekend with jazz musicians Billy Hart, Yotam Silberstein and Omer Avital. These jazz masters are joining forces for a night of musical excellence that jazz connoisseurs and casual listeners alike can enjoy. General admission tickets are $35 and VIP tickets are $55 online.

Hispanic Heritage Month Karaoke

4-9 p.m. Friday

Maggie Daley Park, 337 E. Randolph St.

Kick off Hispanic Heritage Month with this karaoke party celebrating Latin American music, with a focus on a genre known as Cumbia. This event, organized with the Chicago Park District and Night Out in the Parks, is free to attend and family friendly.

Credit: Provided
A previous iteration of WingOut Chicago in the heart of Wrigleyville.

WingOut Chicago

Varying hours Saturday-Sunday

Gallagher Way, 3635 N. Clark St.

Taste award-winning chicken wings and sauces just steps away from Wrigley Field. Vote for your favorites in multiple categories, including Best Kick, Most Original and Best Original. There will also be cold beverages, an expanded food selection, live music, games and more. Tickets ranging from $20-149 are available online.

African Festival Of The Arts

10 a.m.-10 p.m. Friday-Monday

Washington Park, 5100 S. Cottage Grove Ave.

This end-of-summer event is a celebration of Black global cultures, and it’s returning to Chicago this weekend for its 34th annual edition. Set up as a “replicated African village,” there will be over 300 vendors, food and drinks, African diaspora music, drumming and storytelling, Afro-Brazilian dancing and so much more. This family-friendly fest offers free admission on Friday and for children under 5. Various ticket packages for $10-375 are available here.


Noon-6 p.m. Saturday-Sunday

On Tour Brewing Company, 1725 W. Hubbard St.

This popular pop-up market and block party features over 60 artisans and vendors, music, games and more. Shop for handmade goods, vintage clothing, art and other goods at this free, family-friendly event. Dogs are also welcome.

Jazz In The Court

Noon-2:30 p.m. Friday

5235 S. Harper Court

Enjoy the final edition of Hyde Park’s Jazz in the Court, a free outdoor concert series sponsored by the University of Chicago, with performances by Isaiah Collier and Jeremiah Collier.

September Craft Picnic

1:30-6 p.m. Saturday

Promontory Point, 5491 S. DuSable Lake Shore Drive

Local group Craft of Color returns with a September picnic this weekend. Grab a blanket and pack your paints, yarns and any other craft supplies to work on while you meet and mingle with fellow crafters.

Credit: Provided
Bikers cycle along Chicago’s lakefront for Bike the Drive.

Fifth Third Bike The Drive

6:30 a.m.–10:30 a.m. biking, 8 a.m.–12:30 p.m. festival on Sunday

Grant Park — Butler Field, 235 S. Columbus Drive.

Lake Shore Drive will be closed to car traffic and taken over by thousands of bikers Sunday morning as part of the 23rd annual Bike the Drive. The event is produced by and benefits Active Transportation Alliance, a nonprofit working to improve walking, biking and public transit in Illinois and neighboring states. Admission is $64 for members of the alliance, $74 for non-members who register in advance and $84 for non-members who register the day of the event. Youth admission is $18. Register here.

Kinzie Industrial Tour

Noon-2 p.m. Saturday

CTA Ashland Station — Pink and Green Line, 1601 W. Lake St.

Take a walk through the Kinzie Industrial District, which was once home to the city’s first railroad line and companies like Heinz and Dixie Cups. Led by historian and preservationist Erica Ruggiero, you can learn all about the area’s history, architecture and development while exploring it’s many breweries, business incubators, coffee roasters and more. The tour will end at Metric Coffee, 2021 W. Fulton St., where you can grab an afternoon pick-me-up with other walkers. Tickets are free, but a $10-20 donation is appreciated to support the tour group, Chicago for Chicagoans.

Ravenswood Industrial Tour

Noon-2 p.m. Sunday

Irving Park Brown Line Station, 1816 W. Irving Park Rd.

Explore the Ravenswood Industrial Corridor with this new tour offered by Chicago for Chicagoans. Local resident and transportation history enthusiast Walter Kiefer will take walkers through the neighborhood’s history, architecture and development, including how transit resources attracted manufacturing powerhouses. After the tour, you can join the group for a drink at Dovetail Brewery, 1800 W. Belle Plaine Ave., one of the many craft brewers that make up Ravenswood’s “Malt Row.” Tickets are free, but a $10-20 donation is appreciated.

Bronzeville Equity Bike Tour

2-4 p.m. Saturday

DuSable Museum of African American History, 740 E. 56th Pl.

Grab your bike or rent out a Divvy to ride along a tour of Bronzeville, organized by the nonprofit Student-led City Communities Empowerment Collective. Registration is $15 per person. Children younger than 12 can attend for free. Sign up online.

Credit: Colin Boyle/Block Club Chicago
Funkadesi performs at Lot Jams in Albany Park on July 20, 2023.

Funkadesi At The South Asia Institute

2-4 p.m. Saturday

South Asia Institute, 1925 S. Michigan Ave.

The South Asia institute is hosting a free afternoon of festivities Saturday, with music and stories from Chicago’s celebrated music group Funkadesi. The band’s music ranges from South Asian classical, folk and film melodies to West African, Caribbean, Reggae, American Funk and more. There will also be a 30-minute, hands-on instrument demonstration for kids. Admission is free but attendees must register online.

The Super Sideshow With The Enigma

7:30 and 9 p.m. Friday, 7 and 9 p.m. Saturday

Sideshow Gelato, 4819 N. Western Ave.

This weekend, catch performances by one of the founding members of the Jim Rose Sideshow, the Enigma, who has been a staple of the sideshow stage since the ’90s. There will also be several guest performers, pros and newcomers alike. Tickets are $20 online. You must be 18 years or older to attend the 9 p.m. shows, as they are more adult-oriented.

Sideshow Film Screening + Q&A With The Enigma

6:30 and 8:30 p.m. Sunday

Sideshow Gelato, 4819 N. Western Ave.

Alongside a weekend of performances, The Enigma will be at Sideshow Gelato for a film screening of the award-winning documentary “Circus of the Scars,” which recounts stories and struggles of the Jim Rose Circus Sideshow. There will be a Q&A after the showing. Tickets are $10 online.

Harry Potter: Magic At Play Pop-Up

11 a.m.-5 p.m. Thursday-Sunday

Water Tower Place, 835 N. Michigan Ave.

Peek into the Dursley’s living room, visit Hagrid’s pumpkin patch, explore the Forbidden Forest and more at a Harry Potter-themed pop-up shop this weekend. There will be 25 percent off select merchandise and chances to win giveaways. Plus, the first 200 guests each day will get free bottles of Butterbeer.

Credit: North Coast Music Festival/ Facebook

PLUS: Four Picks From Our Partners At

Big Bubble Rave

9 p.m. Friday

House of Blues, 329 N. Dearborn St.

Bop to the best of Bikini Bottom with Big Bubble Rave on Friday night.

Fatboy Slim

10 p.m. Friday

PRYSM, 1543 N. Kingsbury St.

Catch legend Fatboy Slim for a show at PRYSM.

North Coast Music Festival

Noon Friday-Sunday

Seatgeek Stadium, 7000 S. Harlem Ave.

Catch the biggest starts in EDM for North Coast Music Festival at Seatgeek Stadium.

Perreolandia – River North Reggaeton Bar Crawl Labor Day Weekend

Noon Sunday

River North, 316 W. Erie St.

Elevate your Labor Day Weekend with Perreolandia, a Reggaeton bar crawl.

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