Find Historic Hotels in Downtown Chicago, IL

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Pick from 129 Downtown Chicago Historic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Palmer House a Hilton Hotel
Exterior
Palmer House a Hilton Hotel
4.0 star property
8.2 out of 10, Very Good, (1511)
"Spacious room"
The price is AED 476
AED 651 total
includes taxes & fees
22 Dec - 23 Dec
Palmer House a Hilton Hotel
Congress Plaza Hotel
Exterior detail
Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (8135)
"I thought the staff was really helpful. I wasn’t a fan of the parking situation but the garage next door was nice to deal with. They just kept calling with stipulations like you can’t come and go with the car easily and because of concerts we wouldn’t have access at times, that kind of thing. It was convenient for transportation, walking, food and other conveniences which was nice. The room was really nice but the air conditioning/heat kept getting stuck on high blast and was too warm for our...
The price is AED 315
AED 378 total
includes taxes & fees
24 Nov - 25 Nov
Congress Plaza Hotel
Millennium Knickerbocker Chicago
Property entrance
Millennium Knickerbocker Chicago
4.0 star property
8.2 out of 10, Very Good, (1781)
"Great location and staff was friendly the whole trip. "
The price is AED 364
AED 522 total
includes taxes & fees
24 Nov - 25 Nov
Millennium Knickerbocker Chicago
Hilton Chicago
Pool
Hilton Chicago
4.0 star property
8.4 out of 10, Very Good, (1463)
"The room was excellent but the hotel did not have a room available for me by 4pm, even when check in is at 3pm. Housekeeping was excellent. "
The price is AED 438
AED 622 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Chicago
Chicago Athletic Association, a Hyatt Hotel
Room
Chicago Athletic Association, a Hyatt Hotel
4.5 star property
9.0 out of 10, Wonderful, (1001)
"amazing rooms very eclectic a little small but you don’t need much much of a room. The bathrooms were fabulous. Class appointment and decoration"
The price is AED 528
AED 730 total
includes taxes & fees
24 Nov - 25 Nov
Chicago Athletic Association, a Hyatt Hotel
The Whitehall Hotel, BW Premier Collection
Exterior
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.2 out of 10, Very Good, (3388)
"Na"
The price is AED 344
AED 414 total
includes taxes & fees
24 Nov - 25 Nov
The Whitehall Hotel, BW Premier Collection
Central Loop Hotel
Exterior
Central Loop Hotel
4.0 star property
8.6 out of 10, Excellent, (1687)
"Location and staff were very good "
The price is AED 353
AED 424 total
includes taxes & fees
22 Dec - 23 Dec
Central Loop Hotel
Warwick Allerton - Chicago
Exterior
Warwick Allerton - Chicago
4.0 star property
8.0 out of 10, Very Good, (2809)
"Room was sufficient for a over night stay"
The price is AED 256
AED 392 total
includes taxes & fees
9 Dec - 10 Dec
Warwick Allerton - Chicago
Staypineapple, An Iconic Hotel, The Loop
Front of property
Staypineapple, An Iconic Hotel, The Loop
4.0 star property
9.2 out of 10, Wonderful, (1002)
"I loved the theming"
The price is AED 544
AED 746 total
includes taxes & fees
8 Dec - 9 Dec
Staypineapple, An Iconic Hotel, The Loop
The Drake
Restaurant
The Drake
4.0 star property
8.6 out of 10, Excellent, (1016)
"we were excited about the landmark status and proximity to the lake."
The price is AED 547
AED 642 total
includes taxes & fees
24 Nov - 25 Nov
The Drake
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.
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Frequently asked questions

What should a history enthusiast expect from a trip to Downtown Chicago?
An afternoon exploring the notable monuments in Downtown Chicago is a draw to those who want to learn about local history. And while you’re here, you can check out the acclaimed theater scene and scenic riverfront. You can also discover the fascinating museums in this vibrant area.
What's the best accommodation in Downtown Chicago that's close to historical sites?
Based on our travel expertise, InterContinental Chicago Magnificent Mile, an IHG Hotel is a top historic hotel bookable on our site and it features free WiFi. Chicago Water Tower is a short 9-minute walk away. Other choices to soak up the local history include Palmer House a Hilton Hotel and Hilton Chicago.
How many historical hotels will I find in Downtown Chicago?
Downtown Chicago has 1387 hotels and other accommodations bookable on Expedia, including 3 hotels designated as historic or close to historic sites.
What are the must-see historical sites and other places in Downtown Chicago?
Downtown Chicago is notable for its monuments and landmarks like Chicago Cultural Center, Michigan Avenue Bridge, and Merchandise Mart. Known for its museums and theaters, cultural venues include Goodman Theater, James M. Nederlander Theatre, and Chicago Theatre. Other popular sights include Michigan Avenue and Navy Pier.
What is a historic hotel like in Downtown Chicago?
By booking a historic hotel, guests can stay someplace that has an officially recognized historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be identified as a historic hotel provided that it’s a place of special interest. Traditional architecture and period features can be admired within the guestrooms or public spaces of such hotels in Downtown Chicago, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
You’ll often hear the term “heritage hotel” in Asia and Europe, wheareas the term “historic hotel” is more commonly used in the U.S. overall though the terms are similar. The physical building and architecture of historic hotels are generally the most significant aspect. For a heritage hotel, mainly, it’s cultural value along with how it influenced the community.
Do historic hotels in Downtown Chicago have modern facilities?
Hotel interiors feature the modern conveniences and safety features you might expect, but every effort is made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, free WiFi, and the amenities found in a hotel will also be available in a historic hotel. When you book a historic hotel in Downtown Chicago, don’t worry that you’ll be staying at a place that’s uncomfortable or rundown.