Title: Book the Best HISTORIC Hotels in Chicago in 2025 | Expedia.ca [Chicago Travel Guide](https://expedia.ca/Chicago.dx178248)[Hotels in Chicago](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[Chicago Vacation Packages](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides) ![Chicago featuring heritage elements, signage and a high-rise building](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/237000/237257-Chicago.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Chicago, IL from CA $187 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chicago Historic Hotels Tonight [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-09-30&endDate=2025-10-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chicago Historic Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/fcdb86cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/89e1318d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/42397db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago 9.0/10 Wonderful (2441) "Great stay " CA $374 CA $484 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/c3e40006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LCD TV](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/2875d29f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room | Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/5ad45e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/b910c9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carleton of Oak Park Oak Park 9.0/10 Wonderful (1034) " the facility was excellent ...........hope to stay there in the future!" CA $170 CA $189 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Chicago-Hotels-Carleton-Of-Oak-Park.h9186.Hotel-Information) ![Gift shop](https://images.trvl-media.com/lodging/34000000/33550000/33542800/33542786/5eb9597a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/34000000/33550000/33542800/33542786/bcc45f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/34000000/33550000/33542800/33542786/f61b7ebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/34000000/33550000/33542800/33542786/024b9d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stella Hotel & Ballroom Downtown Kenosha 9.4/10 Exceptional (1017) "Great stay for the area!" CA $124 CA $140 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Milwaukee-Hotels-The-Stella-Hotel-Ballroom.h33542786.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/36353a6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, River View](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/ccc588cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/7b6786ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/8ea7678b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Indigo Naperville Riverwalk by IHG Naperville 9.4/10 Exceptional (1000) "Outstanding property & stay!" CA $211 CA $271 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Indigo-Naperville-Riverwalk.h15662531.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/2123ebc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/1ef45bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/33447feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/01818050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harrah's Joliet Casino & Hotel Joliet 8.4/10 Very good (1002) "Room was very nice and I loved the pictures hanging on the wall. Very convenient for us to walk to the Rialto Theater." CA $209 CA $267 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Joliet-Hotels-Harrahs-Joliet-Casino-Hotel.h554417.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/10200/10101/637a897b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/10200/10101/b9f313ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/10200/10101/9080afa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/10200/10101/39661b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance Chicago Glenview Suites Hotel Glenview 8.8/10 Excellent (1000) "Lovely and unique hotel! Great price for beautiful, clean, conveniently located hotel. " CA $166 CA $187 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Glenview-Suites-Hotel.h10101.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/ed8d4a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/699e81d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/83dc9e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A quiet stay while you are away Oak Park 9.8/10 Exceptional (32) "We stayed a few nights and everything was nice and clean. Thank you!" CA $81 CA $268 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106890000/106887100/106887100/b74c585b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106890000/106887100/106887100/b85d7640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106890000/106887100/106887100/w1272h915x0y0-eaa5285d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106890000/106887100/106887100/9842ef3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 BR • Theater Room • Gym • Walk to Lincoln Park! Lincoln Park 9.8/10 Exceptional (15) "This place was great! In a really nice area of Chicago too. " CA $240 CA $970 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Chicago-Hotels-Walk-To-The-Beach-Theater-Coffee-Bar-Games-Gym.h106887100.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/59f4093c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/66d4fb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/57dfa3ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/db5aefbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Home Run 4 Bedroom, 2 Bathroom Lakeview 9.6/10 Exceptional (18) "Would definitely stay there again " CA $806 CA $1,702 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-4-Bedroom-With-Pool-Table-Steps-From-Wrigley-Field-Sleeps-9.h34821849.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/3c71ed9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/a0078d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/73f8ab11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/81bc10e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms Lakeview 9.0/10 Wonderful (14) "We loved the location and the VRBO itself. Clean, stocked with essentials, and easy to communicate with!" CA $806 CA $1,702 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Chicago-Hotels-Featured-On-The-Travel-Channel.h35179280.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-15&endDate=2025-10-16®ionId=178248&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chicago Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Very Clean Hotel, me and my friend enjoyed our stay here. It is an older hotel but the room was really nice " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Rooms were clean and staff were always happy to help " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "We had a fantastic stay at the Embassy Suites by Hilton Chicago Downtown River North. Our suite was impressively clean and offered plenty of space to spread out, which made it especially comfortable for a multi-day visit. Everything felt well maintained and tidy, which gave us peace of mind right from the start. The location was another highlight. Being in River North meant we were close to great restaurants, shopping, and attractions, and having the subway nearby made getting around the city easy and convenient. It was the perfect base for exploring Chicago. Breakfast was outstanding and far above the standard hotel fare. There were lots of options to choose from, including fresh fruit, pastries, hot items, and the standout feature—a station for custom-made omelets. It was a great way to start each day, and the variety meant there was something for everyone. Overall, Embassy Suites River North checked all the boxes: clean, spacious, well-located, and with excellent breakfast to top it off. We would happily stay here again on our next trip to Chicago." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "Room was a little run down, but everything was amazing!" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "It was great. Juat wish there was a fridge and microwave in the room." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Everything was on point" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Clean room, free wine bottle and water bottles were provided daily. Great location! Everything within 15-20 minute walk. Omar, the bartender was excellent and super friendly! Had great suggestions on where to go to eat and entertainment and made great drinks! I would stay there again and great price too! " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Holiday Inn Chicago Dwtn - The Mart by IHG](//images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "Great location. " [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "View was fantastic. All staff were friendly. Good location; walking distance Navy Pier." [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ## Frequently asked questions ### What can a history enthusiast expect from a trip to Chicago? > A trip to the notable monuments in Chicago will be a draw for the historian and history buff. And while you're here, you can check out the acclaimed theater scene and fascinating museums. You can also take time at the popular shops in this vibrant area. ### What's the best place to stay in Chicago that's close to historical sites? > Based on our travel expertise, [InterContinental Chicago Magnificent Mile by IHG](https://www.expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) is a top historic hotel bookable on our site and it features free WiFi. Merchandise Mart is a short 15-minute walk away. A couple of other options near historic sites include [Palmer House a Hilton Hotel](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) and [Hilton Chicago](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information). ### How many historically relevant hotels are there in Chicago? > In Chicago, there are 5351 hotel accommodations bookable on Expedia, including 18 historic hotels or hotels close to historic sites. ### What are the most important historical places and other sights in Chicago? > Chicago is notable for its monuments and landmarks like Rookery, Chicago Cultural Center, and Chicago Board of Trade Building. Known for its theaters and museums, cultural venues include CIBC Theatre, Symphony Center, and Chicago Symphony Orchestra. Other popular sights include Michigan Avenue and Navy Pier. ### What is a historic hotel like in Chicago? > Guests who choose historic hotels have the opportunity to stay in a place recognized with a national historic designation. Historic hotels throughout the world can take the form of stately homes, palaces or even lodges, old police stations or skyscrapers. These types of hotels in Chicago often retain authentic characteristics like traditional architecture and period features in guestrooms or communal spaces. ### What is the difference between a historic hotel and a heritage hotel? > They are quite similar. "Historic hotel" is a term often used in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to focus on the architecture and building. Heritage hotels draw their meaning mainly from the cultural value and how it influenced the community. ### Do historic hotels in Chicago have modern facilities? > Yes, efforts are made to preserve historic facades and treasured traditions, while interiors have safety features and modern conveniences. Tourists who book a stay can expect the usual amenities from a contemporary hotel such as Smart TVs, WiFi, and updated bathroom facilities. 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[Inns in Madison-Wabash Station](https://www.expedia.ca/Madison-Wabash-Station-Inns.d6210251-aaInns.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Waterpark-Hotels.0-n800025-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Winery-Hotel.0-n800025-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Magnificent Mile Hotels](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels) - [Hotels near Millennium Park](https://www.expedia.ca/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels) - [Hotels near Monroe Station](https://www.expedia.ca/Monroe-Station-Hotels.d6189309.Travel-Guide-Hotels) - [Houseboats in Monroe Station](https://www.expedia.ca/Monroe-Station-Houseboats.d6210064-aaHouseboats.Travel-Guide-Accommodation) - [Hotels near Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Hotels.0-l6175173-0.Travel-Guide-Filter-Hotels) - [River North Hotels](https://www.expedia.ca/River-North-Chicago-Hotels.0-n6350695-0.Travel-Guide-Filter-Hotels) - [Hotels near State Street](https://www.expedia.ca/State-Street-Hotels.0-l6175182-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Adults-Only-Resorts.0-n800024-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-All-Inclusive-Hotel.0-n800024-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Beach-Hotel.0-n800024-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Best-Western.0-n800024-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Boutique Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Boutique-Hotel.0-n800024-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Cheap-Hotels.0-n800024-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Club Quarters Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Club-Quarters.0-n800024-0--bClubQuarters.Travel-Guide-Filter-Hotels) - [Destination Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Destination-Hotels.0-n800024-0--bDestinationHotels.Travel-Guide-Filter-Hotels) - [Fairmont Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Fairmont.0-n800024-0--bFairmont.Travel-Guide-Filter-Hotels) - [Family Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Family-Hotel.0-n800024-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Golf-Hotel.0-n800024-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hilton-Hotels.0-n800024-0--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Honeymoon-Hotels.0-n800024-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Early-Check-In.0-n800024-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Pool.0-n800024-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Balconies.0-n800024-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Bar in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Bar.0-n800024-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Airport-Shuttle.0-n800024-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - 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[Kimpton Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Kimpton-Hotels.0-n800024-0--bKimptonHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-LGBT-Friendly-Hotel.0-n800024-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Lake Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Lake-Hotels.0-n800024-0-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Luxury-Hotel.0-n800024-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Marriott-Hotels-Resorts.0-n800024-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Oceanfront-Hotels.0-n800024-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Pet-Friendly-Hotel.0-n800024-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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Daley Center](https://www.expedia.ca/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide) - [Car rentals near The Loop](https://www.expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in The Loop](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in The Loop](https://www.expedia.ca/Enterprise-Car-Rentals-In-The-Loop.d800024-c15.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in The Loop](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-The-Loop.d800024-c19.Car-Rental-Guide-Suppliers) - [Oryx Rent A Car Rental Cars in The Loop](https://www.expedia.ca/ORYX-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c1059.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in The Loop](https://www.expedia.ca/Payless-Car-Rentals-In-The-Loop.d800024-c38.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in The Loop](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-The-Loop.d800024-c33.Car-Rental-Guide-Suppliers) - [Routes Rental Cars in The Loop](https://www.expedia.ca/Routes-Car-Rentals-In-The-Loop.d800024-c1101.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in The Loop](https://www.expedia.ca/Sixt-Car-Rentals-In-The-Loop.d800024-c35.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in The Loop](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-The-Loop.d800024-c45.Car-Rental-Guide-Suppliers) - [Book Historic Hotels in Chicago on Expedia.com](https://www.expedia.com/Chicago-Hotels-Historic-Hotel.0-0-d178248-tHistoricHotel.Travel-Guide-Filter-Hotels)