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We loved staying at the Chicago Athletic Association! It has a nice rooftop that becomes a club a night with a line out the door but guests can access it at any time. It’s a great location within walking distance to a ton of stuff.
Chief
Hmmm Chicago isn’t exactly the place to come for pools. You’ll have to go really high end to get an outdoor pool - I think the peninsula, Waldorf, viceroy, and langham have pools. Outdoor pools aren’t very common here since we can’t use them very much.
There’s also a hotel called Midtown that is connected to a health club that has a great pool (and amazing gym). It’s not right downtown though so if you’re looking for more than just hotel + pool probs wouldn’t be great.