Nick in the Loop

Nick in the Loop

Drinking Around the Kimpton Gray Hotel: Boleo, Vol. 39, and La Bella Trattoria

The hotel has three very different concepts within its walls. You can go from slurping margaritas in the sunshine to sipping Manhattans in a low-lit lounge in seconds.

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Nick Kindelsperger
Aug 18, 2026
∙ Paid

The Kimpton Gray Hotel doesn’t exude the flashy Gilded Age opulence of the Palmer House or the ornate Gothic ambiance of the Chicago Athletic Association. Instead, it’s stately and understated, with a neoclassical design — think lots of marble — that befits the former regional office of the New York Life Insurance Company.

It’s also quietly one of the best places to grab a drink and a snack in the Loop, if for the variety alone. The hotel has three very different concepts within its walls, each on a separate level and with its own ambiance. You can go from slurping margaritas in the sunshine to sipping Manhattans in a low-lit lounge in seconds.

What better way to get to know them than by grabbing a drink and a snack at each?

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