The Best Places to Drink and Stay in The Loop

The vaulted ceilings and Venetian Gothic stonework on Michigan Avenue give away that this was never meant to be a hotel, and it wasn't, for most of its life. The Chicago Athletic Association is now a boutique hotel under Hyatt's Unbound Collection, holding a Michelin Key, and the bones of the old private club, once restricted to the city's male elite, do most of the atmospheric heavy lifting without anyone having to try too hard.

1. Michelin Guide 1 Key

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Cindy's is a rooftop cocktail bar on top of the Chicago Athletic Association, with a terrace looking over Millennium Park and Lake Michigan. It's a hotel bar, so expect dressed-up visitors, bachelorette sashes, and relatives in town, plus plates meant for three or four people to share. Regional Top 10 for hotel bars at the Spirited Awards, which is one more reason the terrace fills up first.

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2. Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Hotel Bar – U.S. Central

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