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What to do in Chicago for Labor Day weekend: Jazz Fest, Bike the Drive and dueling dance music festivals

August 28, 2025 by Chicago Tribune

Our picks for events in and around Chicago this weekend.

Bike the Drive

If the Lakefront Trail feels a little too cramped, this is your weekend. Hop on your bike and join this annual rite marking the unofficial end of summer. You and your fellow cyclists will have the road all to yourselves.

6:30 a.m.-11:15 a.m. Aug. 31 on DuSable Lake Shore Drive; tickets $18-$104 at bikethedrive.org

Chicago Jazz Festival

Monty Alexander, Kermit Ruffins & the Barbecue Swingers, Eliades Ochoa, Patricia Barber, Gary Bartz NTU Troop and the Ari Brown Quintet top the bill at this year’s Chicago Jazz Festival. With four stages — including one dedicated to the next generation of jazz — the weekend continues to feature a robust lineup.

Through Aug. 31 in Millennium Park, 201 E. Randolph St.; more details on the free event at chicago.gov

ARC Music Festival and North Coast Music Festival

House music in Union Park or electronic dance in Bridgeview? You’ve got three days to pack in dozens of acts across both. North Coast Music Festival celebrates its 15th anniversary and its evolution from a cross-genre festival to one more focused on EDM. Meanwhile, ARC Music Festival aims to build on Chicago’s house history. It’s a long weekend; get ready to dance it away.

Both festivals run through Aug. 31. ARC is in Union Park, 1501 W. Randolph St.; tickets from $189 at arcmusicfestival.com. North Coast is on the SeatGeek Stadium campus, 7000 S. Harlem Ave., Bridgeview; tickets from $169.63 at northcoastfestival.com

Gerard Way leads My Chemical Romance at Riot Fest in Chicago's Douglass Park on Sept. 16, 2022. (Chris Sweda/Chicago Tribune)
Gerard Way leads My Chemical Romance at Riot Fest in Chicago’s Douglass Park on Sept. 16, 2022. (Chris Sweda/Chicago Tribune)

My Chemical Romance

No new release from My Chemical Romance, but instead a celebration of their nearly 20-year-old LP “The Black Parade.” Expect the band to play the full album along with a second set of hits.

7 p.m. Aug. 29 at Soldier Field, 1410 Special Olympics Drive; tickets from $463.80 at soldierfield.com

The Lumineers

The Lumineers’ latest album, “Automatic,” feels so much of the moment that it doesn’t seem strange that a Soldier Field-sized crowd would be ready to board the band’s “black sedan of depression.” Their newer, more introspective songs will be offset by their earlier foot-stompers — and almost certainly an “Ophelia” sing-along. Bonus: St. Vincent is on the bill along with Lake Street Dive.

6:30 p.m. Aug. 30 at Soldier Field, 1410 Special Olympics Drive; tickets from $61.20 at soldierfield.com

The Beaches

The Beaches headline the Chicago stop on Rolling Stone’s four-city “Gather No Moss” tour, designed to showcase exciting new rock acts. Earlier this month, Rolling Stone called The Beaches’ latest LP, “No Hard Feelings,” an album that would “rip open … hearts and get you dancing.” The all-woman, alt-rock band from Toronto will be joined by Hello Mary and Brennan Wedl. Other stops of the tour have featured Mk.gee, Wet Leg and MJ Lenderman.

8 p.m. Aug.29 at The Salt Shed, 1357 N. Elston Ave.; tickets from $48.05 at rollingstone.com

Participants spend the morning riding on DuSable Lake Shore Drive through Grant Park on Sept. 1, 2024, during the annual Bike the Drive event by the Active Transportation Alliance. (Brian Cassella/Chicago Tribune)
Participants spend the morning riding on DuSable Lake Shore Drive through Grant Park on Sept. 1, 2024, during the annual Bike the Drive event by the Active Transportation Alliance. (Brian Cassella/Chicago Tribune)

Babymonster and fromis_9

No demon hunting, but you can still take your K-pop pick this weekend. Babymonster at Allstate Arena or fromis_9 at Chicago Theatre? So many catchy hooks, so many cute costumes. Sheesh!

Babymonster is at 7:30 p.m. Sept. 2 at Allstate Arena, 6920 N. Mannheim Road, Rosemont; tickets from $60.35 at rosemont.com. Fromis_9 is at 7:30 Aug. 30 at the Chicago Theatre, 175 N. State St.; tickets from $100.55 at msg.com. 

Zakir Khan

A couple of weeks after playing Madison Square Garden, Indian comedian and storyteller Zakir Khan brings his act to the Chicago Theatre. With bits about first crushes and middle-class life, Khan performs the entire show in Hindi. It’s already sold out.

7 p.m. Aug. 31 at the Chicago Theatre, 175 N. State St.; tickets at msg.com

“Lurker”

A promising debut film from “Beef” and “The Bear” writer-producer Alex Russell opens this weekend at the Music Box Theatre. That alone might be enough reason to head to the show, but two “Lurker” screenings come with an incentive: a live Q&A with Russell and actors Théodore Pellerin and Zack Fox. Writer-producer Gillian Flynn (“Gone Girl”) moderates the Aug. 30 event; Steve Prokopy, of the Music Box and Third Coast Review, handles the Aug. 29 Q&A.

7 p.m. Aug. 29-30 at Music Box Theatre, 3733 N. Southport Ave.; tickets $13 at musicboxtheatre.com 

Meet Me on Milwaukee

If Times Square can do it, why not Wicker Park? For one Sunday a month starting this weekend and running through October, the Wicker Park & Bucktown Chamber of Commerce is piloting a program to “pedestrianize” a vital neighborhood artery. Streets will close to vehicles to allow for exercise classes, outdoor dining, live acoustic music and sidewalk sales. Check it out — and plan commutes accordingly.

10 a.m.-5 p.m. Aug. 31 on Milwaukee Ave. between Damen/North and Ashland Avenues; details on the free event at the1stward.com

Have something to do around Chicago? Email events to day.chitribevents@gmail.com.

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