Search for Cheap Deals on
Historic Hotels in Chicago

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured Chicago Historic Hotels

Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
Palmer House a Hilton Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
Millennium Knickerbocker Chicago
Millennium Knickerbocker Chicago
4 out of 5
163 East Walton Place, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Millennium Knickerbocker Chicago
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Hilton Chicago
Chicago Athletic Association, a Hyatt Hotel
Chicago Athletic Association, a Hyatt Hotel
4.5 out of 5
12 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition ...
Chicago Athletic Association, a Hyatt Hotel
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
105 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the restaurant and the helpful ...
The Whitehall Hotel, BW Premier Collection
Central Loop Hotel
Central Loop Hotel
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
Central Loop Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
Warwick Allerton - Chicago
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The Loop
4 out of 5
1 W Washington St, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant ...
Staypineapple, An Iconic Hotel, The Loop
The Drake
The Drake
4 out of 5
140 E Walton Place, Chicago, IL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
The Drake
InterContinental Chicago Magnificent Mile, an IHG Hotel
InterContinental Chicago Magnificent Mile, an IHG Hotel
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
InterContinental Chicago Magnificent Mile, an IHG Hotel
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
4 out of 5
500 South Dearborn Street, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.