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Featured Chicago Historic Hotel

See all 908 Hotels in Chicago
Write Inn Hotel

Write Inn Hotel

211 N Oak Park Ave, Oak Park
2.5 out of 5.0
3.8 out of 5 (268 reviews)
CLOSE TO THE FLW DISTRICTStayed here for the Housewalk and found it more convenient than the other hotel in town. We were a little concerned about previous visitors comments, but found this hotel very charming. Yes it is old but it appears it is going under renovation and we found the room in nice shape.
  23 May 2017

C$167

C$167
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.3 out of 5 (155 reviews)
Great locationObviously an older building, but it has history. Housekeeping comes at 9am. Lots of natural lighting. Room didn't come with shampoo/conditioner, but we got some upon request. Loved the decor though.
  28 Jun 2017

C$132

C$132
Hotel Blake, an Ascend Hotel Collection Member

Hotel Blake, an Ascend Hotel Collection Member

500 South Dearborn Street, Chicago
3.0 out of 5.0
4.4 out of 5 (702 reviews)
Perfect Chicago HotelGreat location, clean rooms, great staff! The doorman "Showtime" provide great advice throughout then stay.
  19 May 2017

C$202

C$202
Millennium Knickerbocker

Millennium Knickerbocker

163 East Walton Place, Chicago
4.0 out of 5.0
4.2 out of 5 (1,950 reviews)
Great location Good hotel for Chicago sightseeing and close to Rush Street nightlife.
  26 Jun 2017

C$144

C$144
Hilton Chicago- Michigan Ave Cultural Mile

Hilton Chicago- Michigan Ave Cultural Mile

720 S Michigan Ave, Chicago
4.0 out of 5.0
4.2 out of 5 (1,535 reviews)
Good hotel and great location on lakeVery friendly staff ! They let me check in very early with no extra charge. Everyone was very friendly and said hello
  6 Jun 2017

C$163

C$163
InterContinental Chicago Magnificent Mile

InterContinental Chicago Magnificent Mile

505 N Michigan Ave, Chicago
4.5 out of 5.0
4.2 out of 5 (957 reviews)
Excellent location right on magnificent mile !!! Perfect location!!! On the mile almost in the middle. Opposite the purple pig and next to Michael Jordan's Steakhouse and Enos with Volare behind it. Staff was very accommodating and rooms were in good condition. Elevators can be a little slow around check in / check out time to on slaughter of people ...
  30 May 2017

C$216

C$216
PUBLIC Chicago

PUBLIC Chicago

1301 N State Pkwy, Chicago
4.0 out of 5.0
4.1 out of 5 (444 reviews)
Great location close to the waterExcellent staff, big room, comfy beds. Second time staying here and would definitely stay again. The carpets in the rooms could use some love but otherwise and the bathroom isn't in the best location in some rooms for privacy. The wifi can be shotty and the elevators take forever. Overall the location ...
  27 Jun 2017

C$192

C$192
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
4.0 out of 5.0
4.2 out of 5 (864 reviews)
A great stay in the LoopStayed for 3 nights over a long weekend. I found the hotel's central location perfect for my needs - just 1km from the river (to the west and the north) with super-easy access to the "L", the subway and Millennium Park. My room was smallish but very clean and serviceable - perfect for a single or ...
  28 Jun 2017

C$168

C$168
Carleton of Oak Park

Carleton of Oak Park

1110 Pleasant St, Oak Park
3.0 out of 5.0
4.3 out of 5 (296 reviews)
Mid Century Modern Hotel conveniently located.Good location in Oak Park. Room was comfortable and restaurant had great breakfast.
  23 May 2017

C$171

C$171
The Palmer House Hilton

The Palmer House Hilton

17 E Monroe St, Chicago
4.0 out of 5.0
4.2 out of 5 (2,441 reviews)
Luxurious, welcoming place to relaxStaying at the Palmer House was a real treat for my daughter and me. Excellent location close to lovely fun.
  27 Jun 2017

C$171

C$171
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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.