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Loser buys pizza
Bucktown · 2 stops · A couple hours
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With friends
Better with backup. Split the small plates, split the bill, split the story you’ll retell wrong for years.
22 Jaunts ·
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Mediterranean Dinner, Tiki Nightcap in River North
Chicago · 2 stops · A couple hours
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River North Candlelit Carnivore Crawl
River North · 2 stops · A couple hours
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Top Chef + Top Shelf
Chicago · 2 stops · A couple hours
NewPerry
Lions, Then Lunch
Lincoln Park · 2 stops · A couple hours
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Lake Shore Ride + Roll
Chicago · 4 stops · Full day
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Brisket First, Cocktails and Board Games After
West Loop · 2 stops · A couple hours
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Fulton Market Staycation
Chicago · 4 stops · Half a day
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Greek Town, then Eat Street
West Loop · 3 stops · Half a day
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The BBQ Chaser You Didn’t Know You Needed
Logan Square · 2 stops · A couple hours
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Lincoln Park Slow Stroll
Chicago · 3 stops · Half a day
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Mag Mile Food Crawl
Chicago · 9 stops · Full day
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Brunch and Browse on Armitage
Lincoln Park · 4 stops · Half a day
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Lincoln Park Window Shopping and Brunch at Blue Door
Lincoln Park · 4 stops · Half a day
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Chicago Riverwalk
Chicago · 5 stops · Half a day
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Old Town Night Out
Chicago · 3 stops · A couple hours
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Tomatoes, Tigers, and Gyros in Lincoln Park
Chicago · 3 stops · Half a day
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Cooking Class + Nightcap
West Town · 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
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Steaks and Cigars in the Gold Coast
Chicago · 2 stops · A couple hours
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Vietnamese + Cocktails on Oak
Chicago · 2 stops · A couple hours
NewPerry
Gold Coast Stroll
Chicago · 5 stops · Half a day