Chicago Hotels

Chicago Boutique Hotels

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Chicago, IL, United States
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Most popular boutique hotels in Chicago
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Excellent, 852 reviews
#1 out of 40 hotels
C$ 405+
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The Peninsula Chicago

The Peninsula Chicago

Excellent, 280 reviews
#2 out of 40 hotels
C$ 444+
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Waldorf Astoria Chicago

Waldorf Astoria Chicago

Excellent, 161 reviews
#3 out of 40 hotels
C$ 408+
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The Langham, Chicago

The Langham, Chicago

Excellent, 549 reviews
#4 out of 40 hotels
C$ 366+
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Raffaello Hotel

Raffaello Hotel

Great, 3,199 reviews
#5 out of 40 hotels
C$ 144+
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Warwick Allerton - Chicago

Warwick Allerton - Chicago

Great, 2,659 reviews
#6 out of 40 hotels
C$ 110+
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Ivy Boutique Hotel

Ivy Boutique Hotel

Great, 416 reviews
#7 out of 40 hotels
C$ 180+
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Eurostars Magnificent Mile

Eurostars Magnificent Mile

Excellent, 1,035 reviews
#8 out of 40 hotels
C$ 159+
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The Whitehall Hotel

The Whitehall Hotel

Great, 1,907 reviews
#9 out of 40 hotels
C$ 96+
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Central Loop Hotel

Central Loop Hotel

Great, 2,177 reviews
#10 out of 40 hotels
C$ 118+
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Hotel Lincoln

Hotel Lincoln

Great, 364 reviews
#11 out of 40 hotels
C$ 156+
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Virgin Hotels Chicago

Virgin Hotels Chicago

Excellent, 768 reviews
#12 out of 40 hotels
C$ 196+
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Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

Excellent, 530 reviews
#13 out of 40 hotels
C$ 200+
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Kinzie Hotel

Kinzie Hotel

Great, 1,565 reviews
#14 out of 40 hotels
C$ 185+
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Chicago Athletic Association

Chicago Athletic Association

Great, 228 reviews
#15 out of 40 hotels
C$ 207+
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Top tips for finding boutique hotels in Chicago

  • The modern and revamped Chicago Athletic Association is considered one of the most beautiful boutique hotels in Chicago. Cindy’s rooftop restaurant, with its spectacular view of Lake Michigan and Millennium Park, is a favorite spot among locals. Or, grab a drink at the Cherry Circle Room, the Shake Shack, or the Game Room, which has great cocktails alongside game tables.
  • If you’re looking for a boutique hotel that feels like you’re just crashing at a friend’s house, the Freehand Chicago is designed like a super-cool friend’s living room. Located in the center of the River North area, it's a short walk from a number of major attractions, and one of the best restaurant districts in the city. For a quick snack, grab a coffee and pastry at the adjacent Café Integral.
  • Nestled in an area of mega-hotels and rental properties, The Publishing House Bed and Breakfast offers a much more personal touch than other hotels in Chicago. Choose from one of the 11 uniquely designed rooms, outfitted in stylish vintage furniture. The incredible breakfast cooked by the hotel owners is one of the highlights, as is their exceptional personal service.
  • The Staypineapple in Chicago’s eclectic Loop is situated in the Reliance Building, listed on the National Register of Historic Places. The modern design seeks to reclaim some of the building’s historic features, including the original ornate grillwork on the elevators. On your way out to explore Chicago, stop at the Pineapple Espresso for a quick cup of coffee and a snack.