Beginning of main content

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save up to 50% on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Best deal
Jun 28 - Jun 30
Tonight
This weekend
Jun 21 - Jun 23
Next weekend
Jun 28 - Jun 30

Featured Chicago Historic Hotels

Estimated price for 1 night/2 adults

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
$119
4.5/5 (121 reviews)

Cool old building and architecture. Pineapple theme was indeed welcoming. Attentive, friendly service.

Reviewed on Apr 26, 2019
HistoricalPet FriendlyDining
Chicago Athletic Association
Chicago Athletic Association
4.5 out of 5.0 12 South Michigan Avenue, Chicago, IL
Free Cancellation
$144
4.5/5 (44 reviews)

The stylish blend of sleekness and rusticism made this a very unique hotel.

Reviewed on May 20, 2019
HistoricalDiningFree Wifi
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago, IL
Free Cancellation
$110
4.1/5 (907 reviews)

The lobby is spectacular. I liked our room (#10-104). Checking in and out was a little bit of a production.

Reviewed on Jun 10, 2019
HistoricalConciergeBar
Millennium Knickerbocker Chicago
Millennium Knickerbocker Chicago
4.0 out of 5.0 163 East Walton Place, Chicago, IL
Free Cancellation
$98
4.1/5 (288 reviews)

The staff, the location, the bed. Pillow could have been a bit more fluffy.

Reviewed on Jun 19, 2019
HistoricalBarConcierge
Hilton Chicago- Michigan Ave Cultural Mile
Hilton Chicago- Michigan Ave Cultural Mile
4.0 out of 5.0 720 S Michigan Ave, Chicago, IL
Free Cancellation
$106
4.1/5 (355 reviews)

HIstoric Value and proximity to landmarks, parks, events, food and shopping.

Reviewed on Jun 17, 2019
HistoricalRecreationPet Friendly
Central Loop Hotel
Central Loop Hotel
4.0 out of 5.0 111 West Adams Street, Chicago, IL
Free Cancellation
$80
4.1/5 (393 reviews)

It was good overall, the room could use some maintenance.

Reviewed on May 16, 2019
HistoricalBusinessDining
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4.0 out of 5.0 701 North Michigan Avenue, Chicago, IL
Free Cancellation
$90
4.0/5 (758 reviews)

Lovely and clean rooms. On the small side, but charming.

Reviewed on Jun 1, 2019
HistoricalConciergeDining
The Whitehall Hotel
The Whitehall Hotel
4.0 out of 5.0 105 E Delaware Pl, Chicago, IL
Free Cancellation
$76
3.9/5 (994 reviews)

We love the Whitehall always have. Simple, clean, accessible and quite.

Reviewed on Jun 17, 2019
HistoricalBarConcierge
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5.0 520 South Michigan Avenue, Chicago, IL
Free Cancellation
$84
3.5/5 (185 reviews)

Location was key. Hotel was kept clean. They dont carry coke products and didnt have a microwave. Other than that I was happy

Reviewed on Jun 18, 2019
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