Best Historic Stays in Chicago, IL
Stays with historic charm in Chicago. Beautifully preserved properties that connect you to the city's heritage without sacrificing modern comfort.
26 verified stays
Also in Chicago
Viceroy Chicago
Editor's Pick
95
HOTEL
$250 - $600/night
Viceroy Chicago
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Rooftop Pool with City Skyline Views
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Art Deco Architecture in 120-Year-Old Landmark
Kimpton Gray Hotel
Editor's Pick
95
HOTEL
$189 - $550/night
Kimpton Gray Hotel
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Rooftop Restaurant & Cocktail Bar (Boleo)
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Historic Chicago Landmark Building
Soho House Chicago
Editor's Pick
94
HOTEL
$275 - $650/night
Soho House Chicago
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80-Foot Rooftop Pool Overlooking West Loop
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Full-Service Cowshed Spa Open to Non-Members
Ambassador Gold Coast - The Chicago Hotel Collection
Verified Excellent
92
HOTEL
$179 - $450/night
Ambassador Gold Coast - The Chicago Hotel Collection
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17th Floor Rooftop Terrace with Outdoor Dining
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Daily Breakfast for Two Included
Villa D' Citta Bed & Breakfast
Verified Excellent
92
HOTEL
$120 - $220/night
Villa D' Citta Bed & Breakfast
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Huffington Post Top 10 Urban B&B Worldwide
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Historic Chicago Graystone Building
SOPHY - Hyde Park
Verified Excellent
92
HOTEL
$159 - $349/night
SOPHY - Hyde Park
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Boutique hotel in historic Hyde Park
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On-site restaurant with locally inspired menu
The Sono Chicago
Verified Excellent
91
HOTEL
$130 - $280/night
The Sono Chicago
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Full kitchen in every suite
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Rooftop deck with city views
The Whitehall Hotel
Verified Excellent
91
HOTEL
$169 - $429/night
The Whitehall Hotel
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Historic 1928 Boutique Hotel on Magnificent Mile
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Kirei Asian Restaurant and Whitehall Lounge On-Site
The Robey
Verified Excellent
90
HOTEL
$180 - $450/night
The Robey
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Rooftop bar with sweeping city views
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Luxury boutique hotel in Wicker Park
L7 CHICAGO BY LOTTE
Verified Excellent
90
HOTEL
$189 - $450/night
L7 CHICAGO BY LOTTE
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Michelin-Recognized Korean American Steakhouse On-Site
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Complimentary Coffee, Espresso & Snacks at Krave Station
Warwick Allerton - Chicago
Verified Excellent
89
HOTEL
$159 - $389/night
Warwick Allerton - Chicago
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Historic Jazz Age Landmark on Michigan Avenue
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Penthouse Tip Top Tap Event Space
Hotel Saint Clair - Magnificent Mile
Verified Excellent
89
HOTEL
$149 - $389/night
Hotel Saint Clair - Magnificent Mile
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Art-Inspired Eclectic Lobby Design
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Craft Coffee Bar On-Site
The Buckingham Hotel
Verified Excellent
88
HOTEL
$120 - $280/night
The Buckingham Hotel
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40th Floor Panoramic Skyline and Lake Views
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Quiet, Secure High-Rise Retreat in the Loop
Staypineapple, An Iconic Hotel, The Loop Chicago
Verified Excellent
88
HOTEL
$150 - $400/night
Staypineapple, An Iconic Hotel, The Loop Chicago
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Historic Burnham Center landmark building
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Complimentary guest bicycles for city exploration
The Inn at Wrigleyville
Verified Excellent
87
HOTEL
$120 - $350/night
The Inn at Wrigleyville
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Full kitchens in every unit
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Steps from Wrigley Field
The Carleton of Oak Park Hotel
Verified Excellent
86
HOTEL
$110 - $200/night
The Carleton of Oak Park Hotel
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Historic Boutique Landmark Over 90 Years Old
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Recently Renovated Suites with Whirlpool Tubs
Freehand Chicago
Verified Excellent
86
HOTEL
$89 - $280/night
Freehand Chicago
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Award-Winning Broken Shaker Cocktail Bar On-Site
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Restored 1927 Art Deco Architecture
Harvey House Inn
Verified Excellent
85
HOTEL
$150 - $260/night
Harvey House Inn
✓
Complimentary breakfast each morning
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Historic Victorian-era architecture
Ray's Bucktown Bed and Breakfast
Verified Excellent
85
HOTEL
$100 - $175/night
Ray's Bucktown Bed and Breakfast
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Free cooked-to-order breakfast daily
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On-site steam room and sauna
Club Quarters Hotel Wacker at Michigan, Chicago
Approved
84
HOTEL
$120 - $280/night
Club Quarters Hotel Wacker at Michigan, Chicago
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Corner of Wacker Drive and Michigan Avenue
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Steps from Millennium Park and the Bean
Majestic Hotel
Approved
84
HOTEL
$109 - $229/night
Majestic Hotel
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Boutique hotel in Lakeview neighborhood
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Steps from Wrigley Field
The Golden Arm
Approved
83
HOTEL
$90 - $180/night
The Golden Arm
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Residential feel in Wicker Park neighborhood
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Walking distance to Division Street dining
House 5863- Bed and Breakfast
Approved
83
HOTEL
$100 - $175/night
House 5863- Bed and Breakfast
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Breakfast included each morning
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Full kitchen available for guest use
The Villa Toscana Guest House
Approved
82
HOTEL
$120 - $220/night
The Villa Toscana Guest House
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Tuscan-inspired Italian villa aesthetic
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Intimate boutique guest house setting
The Willows Hotel
Approved
82
HOTEL
$109 - $229/night
The Willows Hotel
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1920s European-style boutique building
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Intimate pension-inspired atmosphere
Ohio House Motel
Approved
81
HOTEL
$90 - $200/night
Ohio House Motel
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On-site parking in dense River North
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Budget-friendly rates in prime Chicago location