Old-School Chicago Sport Hotel from $152

Hoping to maintain your fitness goals while on vacation? With a luxe stay at the Chicago Athletic Association Hotel, you can have the best of both! This four-star hotel pays tribute to the city's sporty heritage through its unique decor. There's a retro gym where you work-out in style, and if you feel like you're in need of a recovery, there's an old-school bar where you can play billiards and shuffleboard. We found a handful of spring dates from $152 — over $100 off typical rates!

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