Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the price guarantee available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Chicago Historic Hotels

See all 867 Hotels in Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.0 out of 5.0
4.2 out of 5 (2,577 reviews)
Great Historic HotelThe Palmer House remains one of Chicago's treasures. The lobby is beautiful and maintains what it was over the decades. The rooms were nice and comfortable. The gentleman who checked us in was awesome and very friendly. I am sorry I didn't get his name but it was around 2:40pm on Saturday the 14th. ...
  16 Oct 2017

C$188

C$188
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.4 out of 5 (451 reviews)
Really enjoyed the history of the hotel and as to the stay no problems whatsoever and the staff was very helpful in every way. Room very clean .
  18 Oct 2017

C$96

C$96
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 (1,596 reviews)
Just fine!I booked my hotel through Expedia and I had to put my card details in with them to book. I planned on paying cash for the hotel when I arrived. They informed me when I got there that they needed a card that had $50 on it for incidentals. I had already put my card on file when I booked and I assumed ...
  16 Oct 2017

C$212

C$212
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

163 East Walton Place, Chicago
4.0 out of 5.0
4.2 out of 5 (2,025 reviews)
Good location Sheets we're like sleeping with paper and we got interrupted twice by housekeeping at 8 in the morning.
  11 Oct 2017

C$147

C$147
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
4.0 out of 5.0
4.2 out of 5 (933 reviews)
The hotel is in a great location and walking distance to many places. The rooms were clean and comfortable. It was on the smaller side but it has a little kitchenette that could be used for a quick bite. The bathrooms were updated. A great hotel in a great location.
  17 Oct 2017

C$139

C$139
The Drake, a Hilton Hotel

The Drake, a Hilton Hotel

140 E Walton Place, Chicago
4.0 out of 5.0
4.3 out of 5 (824 reviews)
Great location in a historic wonderful hotel.The room was nice and big overlooking the lake , was very comfortable. The morning breakfast was incredible with lots of choices and the staff could not have been more helpful.,
  22 Sep 2017

C$242

C$242
Chicago Athletic Association

Chicago Athletic Association

12 South Michigan Avenue, Chicago
4.5 out of 5.0
4.6 out of 5 (286 reviews)
Beautifully updated hotelThis hotel is swanky and centrally located overlooking Millennium Park. The amenities are outstanding; very masculine, but comfortable for all types. Several restaurants, bars, lounges, game room, and the best rooftop in the city.
  18 Oct 2017

C$177

C$177
Carleton of Oak Park

Carleton of Oak Park

1110 Pleasant St, Oak Park
3.0 out of 5.0
4.3 out of 5 (315 reviews)
Great Old Hotel in a great locationVisited my daughter who lives in Oak Park. Beautiful old hotel in a great section of Chicago. Close to the rail line, great restaurants, and wine bars. Hotel has two good restaurants - Phil's is a sports bar and the other is a more formal dining room. Tour the Frank Lloyd Wright House and surrounding ...
  16 Oct 2017

C$162

C$162
Write Inn Hotel

Write Inn Hotel

211 N Oak Park Ave, Oak Park
2.5 out of 5.0
3.8 out of 5 (273 reviews)
The hotel is comfortable for a stay when you do not plan to be in the room much of the day. There was no closet or accommodation to hang clothes. The room was small and tidy with the usual amenities; namely, microwave, refrigerator, television.
  26 Sep 2017

C$156

C$156
Hotel Lincoln

Hotel Lincoln

1816 N Clark Street, Chicago
4.0 out of 5.0
4.3 out of 5 (726 reviews)
Nice hotel close to the lake and Old TownIt's an older building but had a lot of character. I very much enjoyed my stay. The staff could not have been more friendly. Cool coffee shop attached and great surrounding area. I have no issues recommending this to others.
  14 Oct 2017

C$179

C$179
Map

Recently booked Chicago hotels

Congress Plaza Hotel
3.0 out of 5.0
Last booking: 6 minutes ago
Best Western Grant Park Hotel
2.5 out of 5.0
Last booking: 7 minutes ago
Super 8 Crystal Lake
2.0 out of 5.0
Last booking: 8 minutes ago
Four Points by Sheraton Chicago O'Hare Airport
3.0 out of 5.0
Last booking: 10 minutes ago
Hotel Indigo Chicago Downtown Gold Coast
3.5 out of 5.0
Last booking: 13 minutes ago
Holiday Inn Chicago North-Evanston
3.0 out of 5.0
Last booking: 14 minutes ago
Holiday Inn Express Hotel & Suites Chicago O'Hare
3.0 out of 5.0
Last booking: 16 minutes ago
Best Western At O'Hare
3.0 out of 5.0
Last booking: 17 minutes ago

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.