The Best Places to Eat and Drink in The Loop
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The awards
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Rank 2. The Gage
Creative British
The awards
- AAA AAA: Three Diamonds
- The Infatuation The Infatuation: The 14 Best Restaurants In The Loop
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Rank 3. Acanto
Italian
The awards
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Rank 3. The Ives
Burger Joint
The awards
- Eater Eater: Chicago’s Best Burgers
- The Infatuation 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.
The awards
- The Infatuation The 14 Best Restaurants In The Loop
- Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Hotel Bar – U.S. Central
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The awards
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Rank 7. Amorino
Italian Dessert
The awards
- The Infatuation The Infatuation: #10 · The Ice Cream Power Rankings
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Rank 7. Beatrix Market
Deep-Dish Pizzeria
The awards
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The awards
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Rank 10. Momento Cantina
Mexican
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.
The awards
- The Infatuation The Infatuation: The 14 Best Restaurants In The Loop