Title: 5 Stars Hotels in Historic Route 66, United States of America from CA $153 - Find Cheap Historic Route 66 Hotels With 5 Stars | 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) ![](https://mediaim.expedia.com/destination/9/17f13edc580f92fbd02b78ad30e73751.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Historic Route 66, United States of America from CA $153 - ![](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 5 Star Hotels Tonight [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2025-11-08&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2025-11-09&endDate=2025-11-10&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2025-11-14&endDate=2025-11-16&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=702654640613646336&startDate=2025-11-21&endDate=2025-11-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Historic Route 66 5 Star Hotels ![Lobby](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Club Suite, 1 Bedroom, Lake View](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/9a653c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/0c7c3240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Mediterranean cuisine](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/71f6a2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Chicago Downtown Chicago 9.8/10 Exceptional (1001) "Excellent stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KEDARNATH CA $672 CA $789 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c35e7743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gym](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4f5517f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trump International Hotel & Tower Chicago Downtown Chicago 9.4/10 Exceptional (1762) "Room was immaculately clean and staff was courteous and attentive. We will definitely stay at the Trump again while in Chicago. Location and views were exceptional! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $553 CA $649 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/d00895ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/56d62feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/ee956af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Chicago Downtown Chicago 9.4/10 Exceptional (999) "Amazing hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $625 CA $734 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, hydrotherapy, aromatherapy](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/6ca152e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/acbf2aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago Downtown Chicago 9.8/10 Exceptional (1000) "Staff is always there for your every need. Excellent clean room. Quiet and luxurious " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marco CA $718 CA $843 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/cc9f9fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/9baa79de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/c47ab94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1000) "This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) william CA $657 CA $771 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2200/2125/f0a7407b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/2200/2125/067ceb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2200/2125/3e8aa782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Studio Suite, Balcony](https://images.trvl-media.com/lodging/1000000/10000/2200/2125/acdcbbc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosewood Inn of the Anasazi Downtown Santa Fe 9.4/10 Exceptional (849) "great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $674 CA $852 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Santa-Fe-Hotels-Rosewood-Inn-Of-The-Anasazi.h2125.Hotel-Information) ![Indoor pool, open 6:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/8f021abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/37b7786f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/82915bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago Downtown Chicago 9.4/10 Exceptional (744) "Everything was perfect. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaitlyn CA $414 CA $486 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) ![Suite, Terrace (Water Tower)](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (LAKE MICHIGAN SUITE) | View from room](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ef2f5d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/6526f50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/3c600fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Hyatt Chicago Downtown Chicago 9.6/10 Exceptional (1001) "beautiful room and hotel great bar!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ravi CA $653 CA $767 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Park-Hyatt-Chicago.h20695.Hotel-Information) ![Rooftop bar](https://images.trvl-media.com/lodging/3000000/2860000/2851500/2851438/89e020ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/3000000/2860000/2851500/2851438/e177092f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar](https://images.trvl-media.com/lodging/3000000/2860000/2851500/2851438/5b370fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, hot tub, body treatments, aromatherapy](https://images.trvl-media.com/lodging/3000000/2860000/2851500/2851438/941b0ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel St Louis Downtown St. Louis 9.4/10 Exceptional (1001) "We’ve stayed at this hotel several times and keep coming back. Great hotel staff and property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darla CA $597 CA $698 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/St-Louis-Hotels-Four-Seasons-Hotel-St-Louis.h2851438.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/11700/11610/b07a93ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11700/11610/ead96afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/11700/11610/38b9cae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/11700/11610/caeb6114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Posada de Santa Fe, A Tribute Portfolio Resort & Spa by Marriott Historic Eastside 8.2/10 Very good (1004) "Wonderful place to stsy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kars CA $302 CA $404 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Santa-Fe-Hotels-La-Posada-De-Santa-Fe.h11610.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/30b68b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/2fe2113a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/4690ab59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/75bfc3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago Downtown Chicago 9.2/10 Wonderful (1002) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $615 CA $722 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-The-Ritz-Carlton.h14447.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/0d225744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/w4000h2645x0y22-fdcb2993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/bd0f84f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/5bfebb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Chicago Downtown Chicago 9.2/10 Wonderful (79) "Top tier " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maurice CA $664 CA $780 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/6200/6132/9a597e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6200/6132/8fec4778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/6200/6132/w4000h2663x0y0-dfd3faff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/6200/6132/dbe99670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, St. Louis Clayton 9.2/10 Wonderful (551) "Room was very spacious. The property was immaculate and the service was attentive without be over bearing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James Anthony CA $732 CA $855 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/St-Louis-Hotels-The-Ritz-Carlton.h6132.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40800/40737/dc73db0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Bunkhouse)](https://images.trvl-media.com/lodging/1000000/50000/40800/40737/807aba16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/50000/40800/40737/93204597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40800/40737/4b0bf4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bishop's Lodge, Auberge Collection Tesuque 9.4/10 Exceptional (87) "This hotel is set on the mountain and has most incredible views, gardens, people, service, food and amenities. It's pricey but it was so worth it to me. My mission of total decompression was accomplished." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine [](https://www.expedia.ca/Santa-Fe-Hotels-Bishops-Lodge.h40737.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/40800/40731/eb9982cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/40800/40731/7f6e9855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40800/40731/753685a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, hot stone massages](https://images.trvl-media.com/lodging/1000000/50000/40800/40731/459f0ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Rancho Encantado Santa Fe Santa Fe 9.4/10 Exceptional (264) "Excelent place" ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Manuel Arturo CA $776 CA $958 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Santa-Fe-Hotels-Four-Seasons-Resort-Rancho-Encantado-Santa-Fe.h40731.Hotel-Information) ![Deep-tissue massages, Swedish massages, massages](https://images.trvl-media.com/lodging/36000000/35210000/35209200/35209175/d0c59f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/36000000/35210000/35209200/35209175/376a5600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (Luminaria) | Private kitchen](https://images.trvl-media.com/lodging/36000000/35210000/35209200/35209175/598e1564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 3 Bedrooms (Luminaria) | Terrace/patio](https://images.trvl-media.com/lodging/36000000/35210000/35209200/35209175/c76355cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn of The Five Graces Downtown Santa Fe 9.8/10 Exceptional (9) "My favorite place to stay in Santa Fe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenn [](https://www.expedia.ca/Santa-Fe-Hotels-The-Inn-Of-The-Five-Graces.h35209175.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/00656023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/3b336ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/c0bd1b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/93a33738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Villa West Town 10/10 Exceptional (2) " " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tomonobu CA $380 CA $915 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Chicago-Hotels-Art-Villa.h115163763.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Historic-Route-66-Hotels.s50-0-d702654640613646336.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Historic-Route-66-Hotels.s50-0-d702654640613646336.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Historic Route 66. ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St, Chicago, IL CA $152 CA $179 total Dec 8 - Dec 9 includes taxes & fees 8.4/10 Very Good! (5,200 reviews) [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency O'Hare Chicago 9300 Bryn Mawr Ave, Rosemont, IL CA $166 CA $189 total Nov 24 - Nov 25 includes taxes & fees 8.6/10 Excellent! (2,120 reviews) [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Warwick Allerton - Chicago 701 North Michigan Avenue, Chicago, IL CA $96 CA $153 total Dec 7 - Dec 8 includes taxes & fees 8.4/10 Very Good! (2,947 reviews) [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) Still don't see what you're looking for? [See all properties in Historic Route 66.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=702654640613646336&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=702654640613646336&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=702654640613646336&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=702654640613646336&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=702654640613646336&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=702654640613646336&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Historic Route 66 Check out the local area in Historic Route 66—home to attractions like National Route 66 Museum and Skelly Field at H.A. Chapman Stadium. [See all hotels in Historic Route 66](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&adults=2®ionId=702654640613646336) ![Woody Guthrie Center featuring outdoor art](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Historic Route 66 Hotel Reviews ## Find out more about Historic Route 66 Luxury is the name of the game at the best 5 Stars hotels in Historic Route 66. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Historic Route 66 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Historic Route 66 hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Historic Route 66 without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Historic Route 66. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Historic Route 66? > The amount you pay for a 5-star hotel in Historic Route 66 can vary depending on when you want to travel and how long you plan to stay, among other factors. Use our price per night filter and other search tools to land the best deal on a high-end getaway. > > > > - Search for the lowest price per night from CA $153 ### What makes a hotel 5 stars in Historic Route 66? > In Historic Route 66, a hotel must provide a certain number of top-notch amenities to earn a 5-star rating. These may include gourmet restaurants, saunas and spas, on-site gyms, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-focused standard of service. You can expect things like concierge services, in-room massages and nightly turn-down services. Some may also offer extra touches such as welcome gifts. ### Are there any 5-star all-inclusive resorts in Historic Route 66? > Our handy filters are the best way to find exactly what you're looking for. Select "5-star" and "All inclusive" to show the most luxurious hotels in Historic Route 66 where your meals, room, entertainment and activities are included in the upfront price. 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