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Loser buys pizza
Bucktown · 2 stops · A couple hours
What’s the plan?
Outings in Chicago from people who’ve done them.
Outings in Chicago
This week’s pick
A couple Chicago favorites. Start at WhirlyBall and humble yourself with a little bumper cars meets jai alai meets - polo? Then grab a slice at one of Chicago’s favorite deep d…
Places that work for a table of six and a group chat that can’t decide.See all ›
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Mediterranean Dinner, Tiki Nightcap in River North
Chicago · 2 stops · A couple hours
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The BBQ Chaser You Didn’t Know You Needed
Logan Square · 2 stops · A couple hours
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Old Town Night Out
Chicago · 3 stops · A couple hours
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Vietnamese + Cocktails on Oak
Chicago · 2 stops · A couple hours
The best spots, whether it’s a first date or your standing Friday plan.See all ›
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River North Candlelit Carnivore Crawl
River North · 2 stops · A couple hours
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Lincoln Park Slow Stroll
Chicago · 3 stops · Half a day
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Tomatoes, Tigers, and Gyros in Lincoln Park
Chicago · 3 stops · Half a day
Room to run, food everyone eats, and a stop for the grown-ups.See all ›
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Saturday Downtown Glenview with the Kids
Glenview · 3 stops · A couple hours
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Streeterville with the Kids
Chicago · 3 stops · A couple hours
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Saturday along Lake Shore with the Kids
Chicago · 3 stops · Half a day
For the crew who never text back but always show up.See all ›
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Brisket First, Cocktails and Board Games After
West Loop · 2 stops · A couple hours
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Burger is a must. Rest of the night is optional.
West Loop · 3 stops · Half a day
What’s the vibe?
Tap one to filter every Jaunt in Chicago
Big tables, easy bookings, and somewhere to end up after.See all ›
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Greek Town, then Eat Street
West Loop · 3 stops · Half a day
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Mag Mile Food Crawl
Chicago · 9 stops · Full day
For people who plan the whole day around lunch.See all ›
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Top Chef + Top Shelf
Chicago · 2 stops · A couple hours
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Brunch and Browse on Armitage
Lincoln Park · 4 stops · Half a day
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Cooking Class + Nightcap
West Town · 2 stops · A couple hours
Pick a neighborhood
12 with Jaunts
Every stop is a walk from the last. Wear the good shoes.See all ›
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Lions, Then Lunch
Lincoln Park · 2 stops · A couple hours
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Gold Coast Stroll
Chicago · 5 stops · Half a day
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Lincoln Park Window Shopping and Brunch at Blue Door
Lincoln Park · 4 stops · Half a day
Side streets first, a great meal at the end.See all ›
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Lake Shore Ride + Roll
Chicago · 4 stops · Full day
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Chicago Riverwalk
Chicago · 5 stops · Half a day
Dark rooms, loud music, and bars that don’t check the clock.See all ›
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Fulton Market Staycation
Chicago · 4 stops · Half a day
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Steaks and Cigars in the Gold Coast
Chicago · 2 stops · A couple hours