The Best Places in The Loop

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2. The Infatuation The 14 Best Restaurants In The Loop

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2. The Infatuation The 14 Best Restaurants In The Loop

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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.

1. The Infatuation The 14 Best Restaurants In The Loop
2. Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Hotel Bar – U.S. Central

Momento Cantina is a sprawling, pink-lit Mexican restaurant with self-serve tequila machines and a soundtrack better suited to a Cancun pool deck than a Monroe Street block. It's the kind of place you'd expect in the West Loop, yet here it sits, a short walk from the symphony. The freshly made corn tortillas carry the menu, showing up under birria, tuna tostadas, and a whole fish in zarandeado sauce.

1. The Infatuation The 14 Best Restaurants In The Loop