The Best Boutique Hotels with Pool in Illinois in 2026

This Wicker Park boutique hotel is iconic. Sumptuous interiors aside, The Robey’s magnificent Art Deco architecture will draw you in and keep you there, Its rooms and suites are nestled in sunny corners of a sky-high structure. Snag one of these for yourself and you’ll get matchless views of the Chicago skyline from the comfort of your hotel room. We think you won”t regret a sunset cocktail or two on the rooftop bar either. The Robey isn’t just fancy cocktails and great views, however. It fills an old office building,… > Read Our Full Review

It’s fairly obvious what makes this one-of-a-kind Bucktown, Chicago boutique hotel special. No matter what type of exercise you like, love, or are curious about, you’ll find it here. Housed on a site with a decades-long history of world-class tennis clubs, the Hotel at Midtown is inside an awe-inspiring sports complex where members enjoy access to multiple pools, hours of fitness classes, and outstanding spa facilities. It’s the ideal place for an active traveler. Our favorite aspect, however, is how well the hotel caters to the other aspects of traveling…. > Read Our Full Review