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Loser buys pizza
Bucktown · 2 stops · A couple hours
12 Jaunts
12 Jaunts ·
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Mediterranean Dinner, Tiki Nightcap in River North
Chicago · 2 stops · A couple hours
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Top Chef + Top Shelf
Chicago · 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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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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Old Town Night Out
Chicago · 3 stops · A couple hours
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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