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Featured Chicago Historic Hotels

See all 945 Hotels in Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.5 out of 5.0
4.2 out of 5 (9,597 reviews)
BeautifulCheck in was easy, room was great, bar was nice, food was good, everyone was friendly.
  12 Dec 2017

C$102

C$102
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.5 out of 5.0
3.6 out of 5 (1,544 reviews)
Nice Hotel and easy commute to tourist attractions
  14 Dec 2017

C$96

C$96
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

163 East Walton Place, Chicago
4.5 out of 5.0
4.3 out of 5 (5,419 reviews)
Great customer services Edward and Scott proved excellent customer service when I checked in. Friendly. Attentive. Thorough.
  13 Dec 2017

C$94

C$94
Hilton Chicago- Michigan Ave Cultural Mile

Hilton Chicago- Michigan Ave Cultural Mile

720 S Michigan Ave, Chicago
4.5 out of 5.0
4.2 out of 5 (4,750 reviews)
Pool and food are great and bathroom is great tooFood and pool is great but staff wasn’t great. There is dirsty lower table and magizines. And seat cover didn’t changed by last night food stained. Bathroom is great innovated. Clean and bland new Cleaning crews and room service for food guys like a jerk there isn’t courtesy First day check in counter ...
  12 Dec 2017

C$124

C$124
Chicago Athletic Association

Chicago Athletic Association

12 South Michigan Avenue, Chicago
5.0 out of 5.0
4.6 out of 5 (1,059 reviews)
Good business stayCheck in was smooth but they didn't tell me about my VIP perks. Doorman and rest of the staff were awesome.
  11 Dec 2017

C$161

C$161
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.5 out of 5.0
4.1 out of 5 (7,200 reviews)
Indpls visitorthe staff was very accomodating, the doorman and valet worked there tail off. (it was very cold and they went above and beyond)
  13 Dec 2017

C$104

C$104
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
4.5 out of 5.0
4.2 out of 5 (3,839 reviews)
Comfortable Stay! Nice view! Clean room , it's much appreciated. Thank you, the location was great !
  9 Dec 2017

C$85

C$85
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.5 out of 5.0
4.1 out of 5 (8,407 reviews)
Enjoyed stayThe hotel met are needs. It was centrally located near Michigan Avenue. It allowed us to shop and drop stuff back off at the room. I will stay here nrxt time as well.
  12 Dec 2017

C$96

C$96
Staypineapple at The Alise Chicago

Staypineapple at The Alise Chicago

1 W Washington St, Chicago
4.5 out of 5.0
4.6 out of 5 (1,373 reviews)
Location and RetroThe location is perfect for seeing a play and shopping. The styling is reflective of Burnham and Root which was a interesting era for Chicago. I enjoyed our stay very much.
  10 Dec 2017

C$120

C$120
The Drake, a Hilton Hotel

The Drake, a Hilton Hotel

140 E Walton Place, Chicago
4.5 out of 5.0
4.4 out of 5 (2,027 reviews)
It was amazing! The hotel was beautiful, the room clean and comfortable, and breakfast was complimentary. I will definitely stay there again and recommend it to friends.
  7 Dec 2017

C$102

C$102
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Historic Hotel Guide in Chicago

It goes without saying that Chicago is a historic city. Come see the legendary sights for yourself during your next trip to Chi-Town.

  • Find the best deals on historical hotels in Chicago
  • Enjoy a wide range of modern amenities
  • Stay close to the major attractions like the Rookery and Chicago History Museum

When you’re ready to begin your tour of the historic city, start at the Chicago Water Tower. This castle structure is unlike anything else in town, and for good reason. The tower was one of the few landmarks that survived the infamous Great Chicago Fire of 1871, which burned down half of the city. As you’re walking around the now-metropolis, look upward. Many of the skyscrapers were built during the Roaring ’20s, and the art deco style is still visible today. If you’re looking to go inside any of the buildings, choose the Rookery. The two-story sunlit entrance was designed by Frank Lloyd Wright in 1905 and is still an impressive sight to behold. Of course, if you want the full scoop on Chi-Town legacy, head to the Chicago History Museum, which includes photos, diaries, letters, clothing, and more local lore.

Once you’re ready to turn in for the night, head back to your choice of historical Chicago hotels. Choose a building that holds a special place in the city’s history, or select a spot that’s simply close to the top landmarks in town. Not to worry about paying skyscraper-high prices on your new or old Chicago hotel; book right here on Expedia.ca to find the top discounts on hotels in Chicago.

Chicago has been on the world’s stage for centuries. Nothing has ever slowed it down—not fire, nor snow, nor sleet. Come see what the fuss is about during your historical tour of this grand city of Illinois.