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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.
The awards strongest first
- The Infatuation The 14 Best Restaurants In The Loop
- Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Hotel Bar – U.S. Central
One number, weighted & current 60
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The neighbors closest first
- Cherry Circle Room Drink · 77
- Chicago Athletic Association Stay · 79
- The Ives Burger Joint Eat · 73
- Acanto Italian Eat · 73
- The Gage Creative British Eat · 76
- Amorino Italian Dessert Eat · 62
- Momento Cantina Mexican Eat · 60
- Potter's Lounge Drink · 62
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