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10 amazing things to do in Chicago over Labor Day weekend

Written by
Grace Perry

Can’t sneak away to Wisconsin or Michigan this Labor Day weekend? No worries! Chicago will be buzzing over Labor Day weekend, so it’s the perfect time to drink in the city. With autumn just around the corner, we’ve got to enjoy these final days of summertime. We’ve got you covered with comedy, music, and food festivals that’ll make you wonder why anyone would ever want to leave Chicago at all.

Eat a ton of lobster

We may be on a freshwater body, but when Chicago does lobster, we do it right. Friday and Saturday of Labor Day weekend, the Great American Lobster Fest is bringing lobster from Boston to Navy Pier. Come hungry.

Catch a crazy midnight circus

On Friday and Saturday, Welles Park will transform into the most bizarre circus you’ve ever seen, thanks to Midnight Circus in the Parks. Marvel at tightrope walkers and acrobats in this unique and intimate setting.

Gnaw on a turkey leg like it’s 1453

Get your joust on at the Bristol Rennaissance Faire in Kenosha, WI, just 90 minutes North of Chicago. Try on your worst European accent of choice to get into full Renaissance character.

Catch the best sketch comedy in Chicago

Labor Day weekend marks the closing shows of the Second City’s 104th sketch revue, Fool Me Twice, Déja Vu. If for no other reason, go so you can brag about it when these comedians are TV stars in a few years.

Groove to the tunes of legendary jazz musicians

The Chicago Jazz Festival takes over Millennium Park and the Cultural Center over Labor Day Weekend. Celebrate the best contemporary jazz musicians around like Liberation Music Orchestra and the Bad Plus.

Laugh with Chicago’s funniest comedians

Why go to a lake house when the best lodge around is at Subterranean? Catch the weekly Lincoln Lodge show, a mainstay for alt Chicago comedy.

Dance, dance, dance!

Queen! is a house music institution. Derrick Carter, Michael Serafini and Garrett David’s Sunday night DJ set always delivers, and with no work on Monday? Well, you’ll have to go see for yourself.

Let the bass drop at a huge music festival

Head back to Union Park for the weekend for North Coast, an EDM and rap-focused music festival promoted by the folks behind Mamby on the Beach and Spring Awakening. This year’s lineup includes Bassnectar, Sleigh Bells, Action Bronson, Juicy J and many more.

See Chicago’s very own talk show

Check out writer-performer Mark Bazer’s the Interview Show, a monthly talk show at the Hideout. Bazer welcomes local artists, cooks, musicians, writers and more to his laid-back, intimate show.

Soak up the final beach days

Slap on the sunscreen and make the most of the gorgeous Chicago beaches while it’s still warm out. Don’t overthink it, just enjoy the summer while it’s here. 

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