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Bulls Fest, Lucha Libre Wrestling, Fiesta Boricua And More: 20 Things To Do In Chicago Labor Day Weekend

The Chicago Jazz Festival, Taste of Polonia, ARC Music Festival, the African Festival of the Arts and Bike the Drive are also on deck.

Fiesta Boricua De Bandera a Bandera.
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CHICAGO — There are plenty of happenings around Chicago this Labor Day weekend.

Kick off the first weekend of the month with this roundup of 20 things to do:

Chicago Jazz Festival

Varying times Thursday-Sunday. Click here for the lineup.

Chicago Cultural Center, 78 E. Washington St.; Millennium Park Harris Theater’s rooftop terrace, 205 E. Randolph St.; and the Jay Pritzker Pavilion, 201 E. Randolph St.

Chicago’s free jazz festival is back at Millennium Park and the Chicago Cultural Center this weekend. Performances are at various times and locations, but they generally start between 11 a.m. and noon, with evening shows running until 9 p.m. Performances are free and do not require reservations. Outside alcohol is not allowed, but alcoholic drinks will be available for purchase at the venues.

Fiesta Boricua

Noon-8 p.m. Saturday-Sunday

Division Street between Western and California avenues

A long-running Puerto Rican festival is back this weekend, bringing island performances, food and more to Humboldt Park’s Division Street. Festgoers can expect “a total immersion into Puerto Rican culture,” organizers said. Fiesta Boricua is free, but a $5 donation is recommended.

Bulls Fest

8 a.m.-9 p.m. Saturday-Sunday

United Center, 1901 W. Madison St.

There will be hoops, art shows, beats and eats all weekend outside the United Center, plus exclusive photo opportunities with Bulls players.

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

2-10 p.m. Friday-Sunday

Union Park, 1501 W. Randolph St.

ARC Music Festival is back this weekend with more than 40 artists. It’s expanding into a three-day fest with headliners Carl Cox, Adam Beyer, Honey Dijon and local Chicago artist DJ Lady D. Tickets are on sale, with three-day general admission passes starting at $309 and one-day passes starting at $139.

Taste of Polonia Festival

5-10:30 p.m. Friday, noon-10:30 p.m. Saturday-Sunday, noon-9:30 p.m. Monday

Copernicus Center, 5216 W. Lawrence Ave.

The fest returns after a two-year pandemic hiatus with music and dance performances with Polish artists, vendors, kid-friendly art events, Polish food, a beer garden and more. It’s been touted as the largest Polish festival in the United States, drawing about 35,000 people each year.

The Great American Lobster Fest

Noon-10 p.m. Friday-Saturday, noon-9 p.m. Sunday

Navy Pier, 600 E. Grand Ave.

This seventh annual Lobster Fest is returning to Navy Pier this weekend. Enjoy lobster flown in from the East Coast, live music, family-friendly games, craft shopping, food and drinks and more. General admission to the festival is free, but you can buy tickets online here starting at $70 for lobster meals, reserved seating areas and more.

Credit: Chicago Labor Day Parade
The Chicago Labor Day Parade was last held in Sept. 2019.

Labor Day Parade In East Side

Noon Saturday

104th Street and Ewing Avenue

The popular parade will feature dozens of floats celebrating Chicago’s unions and labor history. Paradegoers will head to Eggers Grove, which has an entrance at 112th Street and South Avenue E. There, attendees can celebrate Eddie Fest with live music, family activities and food.

Credit: Jorge Acosta/Provided
Lucha Libre In the Park brings masked wrestlers to Unity Park.

Lucha Libre In The Park

Noon-1:30 p.m. Saturday

Unity Park, 2636 N. Kimball Ave.

Pop-up wrestling matches are making their way back to Logan Square this weekend. Lucha Libre wrestlers — also called luchadores — will perform complex acrobatic moves while wearing colorful masks and costumes.

Credit: African Festival of the Arts/ Twitter
African culture will be on display at the African Festival of the Arts this weekend.

The African Festival Of The Arts

Noon-10 p.m. Friday and 10 a.m.-10 p.m. Saturday-Monday

Washington Park, 5100 S. Cottage Grove Ave.

The African Festival of the Arts is returning for Labor Day weekend after years of not being held due to the pandemic. There will be arts and crafts, cooking classes, musical performances, vendors, a drum circle and more.

Tickets are available online or at the event. Advance general admission tickets are $30, general admission tickets on site are $40, an advance weekend pass is $75 and a weekend pass at the event is $120. There are discounts for older people and children.

Lincoln Square Greek Fest

5-11 p.m. Friday, 3-10 p.m. Saturday, 11:30 a.m.-10 p.m. Sunday, 11 a.m.-8 p.m. Monday

St. Demetrios Greek Orthodox Church, 2727 W. Winona St.

Enjoy Greek food, pastries, loukoumades, live performances from bands and a Greek dance troupe and a Hellenic marketplace at the annual fest.

West Loop Art Fest

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

West Fulton and North Sangamon streets

The fest returns for its fourth year with four blocks of art available for purchase at a variety of price points. There will also be live music.

Jazz At Maxwell Street Market

10 a.m.-1:15 p.m. Sunday

800 S. Desplaines St.

The Maxwell Street Market is celebrating Chicago jazz Sunday with performances by the Chicago Jazz Philharmonic and Hunter Diamond. The street market is a Chicago tradition and takes place Sundays through Dec. 18 with an eclectic mix of handmade crafts, resale clothing, live music, family fun, street food and more.

La Esquina Expo And Fundraiser

5 p.m. Friday-12:30 a.m. Saturday

Thalia Hall, 1807 S. Allport St.

La Esquina Community Center is hosting its first exposition and fundraiser Friday. There will be exhibitions, demonstrations and performances in various artistic fields, including muralism, photography and music. The free event is open to the public and people of all ages, but a $5 donation is suggested.

After 9 p.m., the event will be strictly for people 17 and older with a $20 cover to benefit La Esquina Community Center programs.

Ghosts Of Old Chicago River North Walking Tour

7:30 p.m. Thursday and Saturday

Meet at the Reid-Murdoch Center, 325 N. LaSalle St., at the north end of the LaSalle Street Bridge

This 2-mile walking tour takes participants through the heart of haunted Chicago and its famous folklore, from the Fort Dearborn Massacre to the city’s ties to “Poltergeist” and “Ghostbusters.” Tickets are available online for $29.

Sundays On State

11 a.m.-6 p.m. Sunday

State Street between Monroe and Lake

This outdoor fest is taking over State Street for the last time this summer. Shop local businesses, partake in dance and fitness classes, enjoy musical and dance performances and more.

Den Theatre Marketplace

10 a.m.-3 p.m. Sundays

Den Theatre, 1331 N. Milwaukee Ave.

A Wicker Park theater known for hosting comedy shows and plays is launching a weekly marketplace to highlight local artists, makers and performers. A local drag queen, DJs, a brass band and more than 30 artists will kick off the first market this weekend.

Sweet Home South Chicago

Noon-6 p.m. Saturday

Commercial Avenue from 88th to 90th streets

The street festival will feature local vendors, live music and more on South Chicago’s Commercial Avenue. It will feature face painting, a bounce house, balloon twisting, a game truck — and local food for a Taste of South Chicago, according to a Facebook event. There will also be a back-to-school giveaway for students and resources from local groups. 

The Creepshow: A Stephen King Film Festival

Varying times Friday-Sunday

Music Box Theatre, 3733 N. Southport Ave.

This three-day event includes a live “The Losers’ Club” podcast recording, exclusive garden screenings, themed drinks, Sunday morning trivia, a costume contest, giveaways, vendors and more. Passes are available online starting at $6 for Music Box Theatre members or $8 for general admission.

Bike The Drive

6:30-10:30 a.m. Sunday

Butler Field in Grant Park, 235 S. Columbus Drive, and various entrances on DuSable Lake Shore Drive

DuSable Lake Shore Drive will be closed to car traffic Sunday morning so cyclists can bike the drive. Thousands of cyclists are expected to attend the fundraising event for the Active Transportation Alliance. Advanced registration is $60 online or $70 the day of the event.

Taste Of Iceland

Various times and locations across Chicago. Click here for the full schedule.

Enjoy Icelandic food and drink, music, literature, films, art and more. The fest will be hosted at locations across Chicago this weekend. Unclaimed tickets are available on a first-come, first-served basis 30 minutes before each event.

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