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The Best Boutique Hotels with Pool in Wicker Park in 2026

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Our choices for this year’s best boutique hotels in, one of Chicago’s most sought after residential neighborhoods, the very lovely Wicker Park!

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Chicago

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The Robey Hotel

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Number of Rooms: 89
Guide Price: Between $200 & $300 per Night
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Address: 2018 West North Avenue
Wicker Park
Chicago
Illinois
60647
Compare it with others in: Boutique Hotels For Families and Boutique Hotels with Pool
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