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Featured Chicago Historic Hotels

Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The Loop
4.0 out of 5.0 1 W Washington St, Chicago, IL
Free Cancellation
$84
4.8/5 (35 reviews)

This is such an iconic historical building, and they did a goob job in maintaining some of the features. But the new bar and restaurant design is terrible ! Such a shame.

Reviewed on Mar 4, 2020
At Staypineapple, An Iconic Hotel, The Loop, guests have access to a fitness center, free WiFi in public areas, and a meeting room. Multilingual staff at the ...
HistoricalPet FriendlyDining
Hotel Blake, an Ascend Hotel Collection Member
Hotel Blake, an Ascend Hotel Collection Member
3.5 out of 5.0 500 South Dearborn Street, Chicago, IL
$159
4.5/5 (24 reviews)

This was a business trip with some vacation peppered in. The staff were so friendly, the room was wonderful, and I couldn't be happier! The hotel is situated within walking distance, or a quick train ride, to everything worth seeing in the city. I'd love to return and get to see what I didn't have ...

Reviewed on Aug 14, 2019
Guests of Hotel Blake, an Ascend Hotel Collection Member enjoy a 24-hour fitness center, free WiFi in public areas, and a 24-hour business center. Valet parking ...
HistoricalDiningFree Wifi
Chicago Athletic Association
Chicago Athletic Association
4.5 out of 5.0 12 South Michigan Avenue, Chicago, IL
Free Cancellation
$161
4.4/5 (28 reviews)

This was such a great place to stay. The games room was so much fun. Cindy's was a great place to just grab a drink and enjoy the atmosphere but there are better and more affordable places to eat within walking distance. The hotel was wonderful and we will be visiting again.

Reviewed on Feb 25, 2020
At Chicago Athletic Association, guests have access to a 24-hour fitness center, a rooftop terrace, and free WiFi in public areas. Self parking is offered for ...
HistoricalDiningFree Wifi
The Homestead Evanston
The Homestead Evanston
3.0 out of 5.0 1625 Hinman Ave, Evanston, IL
4.4/5 (33 reviews)

Definitely an older hotel but staff amazing, location was good. I would stay here again!

Reviewed on Aug 17, 2019
Guests of Graduate Evanston enjoy a 24-hour fitness center, free WiFi in public areas, and a business center. Self parking is available for USD 14 per day. The ...
HistoricalParkingDining
The Drake, a Hilton Hotel
The Drake, a Hilton Hotel
4.0 out of 5.0 140 E Walton Place, Chicago, IL
Free Cancellation
$99
4.3/5 (265 reviews)

Excellent service from the beginning to the end. The hotel was beautiful, amazing restaurant with live music and even have a few cafes.

Reviewed on Mar 15, 2020
The Drake, a Hilton Hotel features a fitness center, WiFi in public areas, and conference space. Parking is available for USD 49.00 per day (USD 71 per day for ...
HistoricalConciergeDining
Central Loop Hotel
Central Loop Hotel
4.0 out of 5.0 111 West Adams Street, Chicago, IL
$89
4.3/5 (104 reviews)

This is perhaps he best hotel I have ever used. The spacious living room in the lobby, the inviting business center downstairs and on the third floor, the happy hours, the gracious staff--were all very inviting. And the location is great.

Reviewed on Mar 7, 2020
Renovated in 2016, Central Loop Hotel offers a 24-hour fitness center, free WiFi in public areas, and a 24-hour business center. Valet parking is offered for ...
HistoricalBusinessDining
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago, IL
4.1/5 (978 reviews)

I’ve been staying at Palmer House for 25 years and it never disappoints!

Reviewed on Feb 12, 2020
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a health club. Parking is available for USD 52 per night (USD 82 per night ...
HistoricalConciergeBar
Millennium Knickerbocker Chicago
Millennium Knickerbocker Chicago
4.0 out of 5.0 163 East Walton Place, Chicago, IL
Free Cancellation
$95
4.1/5 (326 reviews)

I felt the bathroom and room itself was a little small. Bed was a little soft. Curtains needed to be cleaned or updated.

Reviewed on Mar 11, 2020
At Millennium Knickerbocker Chicago, guests have access to a fitness center, free WiFi in public areas, and conference space. Self parking is offered for USD ...
HistoricalBarConcierge
Carleton of Oak Park
Carleton of Oak Park
3.0 out of 5.0 1110 Pleasant St, Oak Park, IL
Free Cancellation
$134
4.0/5 (50 reviews)

They have Friendly and very helpful staff. The outside rooms attached are nice to stay in for the ease of access to your vehicle and outside.

Reviewed on Jul 26, 2019
Carleton of Oak Park features a fitness center, free WiFi in public areas, and conference space. If you plan to drive, free parking is available. Front-desk ...
HistoricalParkingFree Parking
Hilton Chicago
Hilton Chicago
4.0 out of 5.0 720 S Michigan Ave, Chicago, IL
4.0/5 (399 reviews)

I like the large rooms, the beds however were not comfortable. The location was also a plus. The staff’s attitude can improve, NONE of the employees I interacted with were friendly, this was shocking to me for HH. They ALL need some serious training, especially the ones answering the phones, good ...

Reviewed on Feb 25, 2020
Guests staying at Hilton Chicago enjoy an indoor pool, a health club, and a spa tub. Valet parking is offered for USD 79.00 per night. The 24-hour front desk ...
HistoricalRecreationPet Friendly
InterContinental Chicago Magnificent Mile
InterContinental Chicago Magnificent Mile
4.5 out of 5.0 505 N Michigan Ave, Chicago, IL
Free Cancellation
$174
4.0/5 (301 reviews)

Beautiful hotel, amazing location, top notch pool and gym compared to other hotels in Chicago. This is one of my favorite places to stay in Chicago! The rooms are small but that is about the only thing I could say could be better. Complementary upgrades on low occupancy days would be a good idea. ...

Reviewed on Jan 13, 2020
InterContinental Chicago Magnificent Mile features a full-service spa, an indoor pool, and a fitness center. Multilingual staff at the 24-hour front desk can ...
HistoricalSwimmingWifi
The Whitehall Hotel
The Whitehall Hotel
4.0 out of 5.0 105 E Delaware Pl, Chicago, IL
Free Cancellation
$89
3.8/5 (997 reviews)

The staff was really friendly and helpful. Hotel was very clean. Older building so the rooms were sort of small but other than that it was a good stay.

Reviewed on Jun 30, 2020
The Whitehall Hotel features a fitness center, free WiFi in public areas, and a meeting room. Self parking is offered for USD 50 per night. The 24-hour front ...
HistoricalBarConcierge
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4.0 out of 5.0 701 North Michigan Avenue, Chicago, IL
$285
3.8/5 (143 reviews)

It was unique better than most hotels that I’ve been in

Reviewed on Mar 2, 2020
At Warwick Allerton - Chicago, guests have access to a 24-hour fitness center, WiFi in public areas, and a conference center. Valet parking is available for ...
HistoricalConciergeDining
Write Inn Hotel
Write Inn Hotel
2.5 out of 5.0 211 N Oak Park Ave, Oak Park, IL
$119
3.6/5 (34 reviews)

The staff was friendly and accommodating and the room was spacious and comfortable

Reviewed on Nov 28, 2019
A local mainstay since 1929, Write Inn Hotel offers free WiFi in public areas, express check-out, and laundry facilities. You can take advantage of free parking, ...
HistoricalFree ParkingParking
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5.0 520 South Michigan Avenue, Chicago, IL
Free Cancellation
$109
3.5/5 (283 reviews)

This was a very beautiful hotel. However, our room wasn't all that clean. There was alot of hair on the bathroom floor and the ceiling was falling apart. But the hotel itself is absolutely gorgeous

Reviewed on Jun 30, 2020
Guests of Congress Plaza Hotel enjoy a fitness center, free WiFi in public areas, and conference space. Valet parking is available for USD 52.00 per night. Multilingual ...
HistoricalConciergeRoomservice

Uncover the Intrigue of a Chicago Historic Hotel

Featuring a variety of historic hotels, Chicago offers travelers a rich tapestry of one-of-a-kind local experiences. Whether you choose opulence or rustic charm, you can embrace life in a different era for a night, a weekend, or an extended stay.

Upgrades and restores
Historic hotels have often been painstakingly restored to reflect their original glory or to update them with a contemporary vibe. You can choose to rough it in humble historic accommodations, or experience the good life in the area's sophisticated restored mansions and original hotels.

Historic hotels allow you to embrace each hotel’s heyday. Sip drinks in a retro bar, relish a candlelit dinner in a lavish dining room, or enjoy a private fire in your own well-appointed suite.

Many historic hotels even feature original grand facades and modern interiors with newly renovated lobbies and rooms. Others have been meticulously restored to reflect every historic detail of the building’s past. Choose how you wish to experience the history of Chicago!

Get a glimpse of the past at a Chicago historic hotel
Whether you’re looking for a retro experience or you want something from a different century, a stay at a famous hotel in Chicago offers an unforgettable escape that will take your vacation to a new and unexpected level.

Discover life in Chicago from a different perspective with a trip back in time and book your historic hotel stay today.

Recent Historic Hotels Reviews

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.