Title: Book the Best Historic Route 66 LUXURY Hotels - Upscale Hotels in Historic Route 66 | Expedia.ca [Historic Route 66 Travel Guide](https://expedia.ca/Historic-Route-66.dx702654640613646336)[Hotels in Historic Route 66](https://expedia.ca/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[Vacation Rentals in Historic Route 66](https://expedia.ca/Historic-Route-66-Vacation-Rentals.d702654640613646336.Travel-Guide-VacationRentals)[Flights to Historic Route 66](https://expedia.ca/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[Historic Route 66 Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Route-66.d702654640613646336.Car-Rental-Guide)[Historic Route 66 Vacation Packages](https://expedia.ca/Historic-Route-66.d702654640613646336.Destination-Travel-Guides) ![North Central Arizona showing signage](https://images.trvl-media.com/place/1218/93b64b3e-64f1-4166-b6ae-c4c686f3ea8b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/1218/93b64b3e-64f1-4166-b6ae-c4c686f3ea8b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Historic Route 66 Luxury Hotels Tonight [Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2026-01-25&endDate=2026-01-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2026-01-26&endDate=2026-01-27&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2026-01-30&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Historic Route 66 luxury hotels ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/83e4c147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/459a3527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/1f085992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/e824a8ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### JW Marriott Chicago [](https://www.expedia.ca/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,002 reviews) "Clean room and great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Derek CA $251 CA $343 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) ![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/6f853099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/d0c2944a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/0a805224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/1893647b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Central Loop Hotel [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,004 reviews) "Clean rooms, very friendly staff, and great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dipayan CA $100 CA $118 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/4bc08adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/72004781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/64fc97f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/5e323fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,012 reviews) "Clean rooms, great staff, and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Romel CA $98 CA $148 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information) ![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/f1ee0c52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/a6af9ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/9f4f3ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### theWit Chicago, a Hilton Hotel [](https://www.expedia.ca/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,006 reviews) "Great location, clean hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maricella CA $179 CA $250 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a68260d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Latin American cuisine](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (2,345 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Blake CA $144 CA $216 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/62385a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/dc5ac11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric The Loop Chicago [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (2,368 reviews) "Will stay again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luzabeth CA $131 CA $188 total includes taxes & fees Feb 20 - Feb 21 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/afa1818a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/a08df61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3,208 reviews) "Hotel staff are nice and the rooms are clean .. This hotel is close to everything , highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria Rochelle CA $128 CA $151 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/a08c52fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) Downtown Chicago 8.8/10 Excellent (2,262 reviews) "amazing stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anani CA $117 CA $137 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/bebf91fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/fbf72db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/32068350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Swissotel - Chicago [](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3,163 reviews) "Place is always top notch..stay here anytime we stay in Chicago." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon CA $156 CA $232 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (2 Room)](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2561x3y0-7e662cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/d34c171a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2556x3y3-aad44a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Chicago, Tapestry Collection by Hilton [](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,517 reviews) "Great location, friendly staff and nice room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Srinivasa CA $78 CA $131 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.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=2026-02-09&endDate=2026-02-10®ionId=702654640613646336&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Historic Route 66 Hotel Reviews ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Clean room & great staff!" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "Yes" [](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "The room was very clean and comfortable! The staff were friendly, especially the Doorman/Valet guy!" [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![L7 Chicago by LOTTE](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42_y.jpg) ### L7 Chicago by LOTTE 10/10 Excellent "Clean room Nice staff Great location. " [](https://expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "ten out of ten experience, will definitely go back in the summer" [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Perfect location " [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Staff were very helpful and friendly. Clean comfortable room. Easy to walk to places from the hotel. Close to Navy Pier. Would stay here again. I’m " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Great staff & awesome location!" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Always a great stay, clean, great breakfast, great pool. 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