Title: Historic Route 66 Vacation Packages & Trips 2025/2026 from CA $492 | 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) ![](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Route 66 Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Top Historic Route 66 Vacation Deals Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $492 per person Nov 27 - Nov 29 found 1 day ago Roundtrip flight included Detroit (DTW) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!! Reviewed on Sep 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-29/?FromAirport=DTW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=EJcZ_mrSrkWeNUdTT7h258ujUVN0CSUE-8AKuzeetgsvzTjqwLOdFd4cs2UMVWyu) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $810 per person Nov 13 - Nov 15 found 1 day ago Roundtrip flight included Detroit (DTW) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Perfect location, beautiful view, nice staffs, excellently maintained room and facility! Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-15/?FromAirport=DTW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=SMW3YWY3Xrca2XgJwmkHodCA1du6_FQ_eCYPm-2kgg1lGdZqTyrlG93a6oPLCffj) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $659 per person Dec 18 - Dec 21 found 1 day ago Roundtrip flight included Detroit (DTW) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Had a great uneventful stay Reviewed on Sep 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-18/2025-12-21/?FromAirport=DTW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=-1lEOHUbIHGWDzvxxjNGDnmptjCP1vQGvx5Ay7w_ZZYGoZhIVoO9A4SoEfZL8vE6) ![The Inn at Vanessie](https://images.trvl-media.com/lodging/1000000/90000/85300/85222/181de913_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Vanessie Downtown Santa Fe CA $1,981 per person Dec 20 - Dec 24 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Albuquerque (ABQ) 8.8/10 Excellent! (1,022 reviews) Travelers most want a clean room free of cleaning smells, a comfortable bed, a decent side chair, a quiet working HVAC system. My room was clean with a comfortable bed. I’d rate my room at 3 stars. Friendly, pleasant staff willing to resolve issues. They seemed to understand that the rooms need refurbished and did their best to make guests happy. I rate hotel staff at 5. Quiet lobby with a great bar, excellent breakfast, excellent simple dinner menu that could be easily overlooked…try the chicken enchiladas plate or the hummus appetizer. The bar is well stocked. I rate the amenities at 5 stars. Absolutely a great location; walkable to museums, plaza, galleries and so much more. Wish the owner would update the rooms! Staying here depends o the level of comfort that you want. Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-24/?FromAirport=YTO&Destination=ABQ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=85222&paandie=true&dealMarker=ITvedxSCB34KIk1NGEwLQ-dtey7rumQBJyTyYYZPXThOOviuRXvH-xCmM65TkBmR) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $891 per person Nov 27 - Nov 29 found 1 day ago Roundtrip flight included Detroit (DTW) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Fantastic stay with excellent staff ! Would 100% recommend and will be returning the next time we are in Chicago. Reviewed on Sep 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-29/?FromAirport=DTW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=EJcZ_mrSrkWeNUdTT7h253kE8PG3_n1u4zsYLCW6SgNXbulF19melOe_HaQ40pwd) ## Ready to book your vacation to Historic Route 66? Choose your dates ## Historic Route 66 Hotel Deals ![Club Quarters Hotel, Central Loop, Chicago](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel, Central Loop, Chicago 111 West Adams Street, Chicago, IL Fully refundableReserve now, pay when you stay CA $187 CA $220 total Oct 30 - Oct 31 includes taxes & fees 8.6/10 Excellent! (3,370 reviews) "Decent property overall." Reviewed on Sep 25, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&selected=565746&PinnedHotelID=565746&HadPinnedHotel=true®ionId=702654640613646336) ![Central Loop Hotel](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/43ee742c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Central Loop Hotel 111 West Adams Street, Chicago, IL Fully refundableReserve now, pay when you stay CA $189 CA $222 total Oct 30 - Oct 31 includes taxes & fees 8.4/10 Very Good! (1,867 reviews) "Friendly and helpful staff. Perfect location!!" Reviewed on Sep 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&selected=2151878&PinnedHotelID=2151878&HadPinnedHotel=true®ionId=702654640613646336) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue, Chicago, IL Fully refundableReserve now, pay when you stay CA $187 CA $220 total Oct 26 - Oct 27 includes taxes & fees 7.8/10 Good! (9,298 reviews) "Grea5" Reviewed on Sep 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=702654640613646336) [See all 19,177 properties in Historic Route 66](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F09%2F2025&endDate=01%2F10%2F2025®ionId=702654640613646336) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia - 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[Southeast Iowa Hotels](https://www.expedia.ca/Southeast-Iowa-Hotels.d6234151.Travel-Guide-Hotels) ### Flights - [Flights to Ohio River Valley](https://www.expedia.ca/Cheap-Flights-To-Ohio-River-Valley.d6233674.Travel-Guide-Flights) - [Flights to Quad Cities](https://www.expedia.ca/Cheap-Flights-To-Quad-Cities.d603001.Travel-Guide-Flights) - [Flights to Southeast Iowa](https://www.expedia.ca/Cheap-Flights-To-Southeast-Iowa.d6234151.Travel-Guide-Flights) - [Flights from Calgary to Quad Cities](https://www.expedia.ca/lp/flights/178245/603001/calgary-to-quad-cities) - [Flights from Calgary to Ohio River Valley](https://www.expedia.ca/lp/flights/178245/6233674/calgary-to-ohio-river-valley) - [Flights from Chicago to Quad Cities](https://www.expedia.ca/lp/flights/178248/603001/chicago-to-quad-cities) - [Flights from Columbus to Quad Cities](https://www.expedia.ca/lp/flights/178251/603001/columbus-to-quad-cities) - [Flights from Dallas to Ohio River Valley](https://www.expedia.ca/lp/flights/178253/6233674/dallas-to-ohio-river-valley) - [Flights from Indianapolis to Quad Cities](https://www.expedia.ca/lp/flights/178266/603001/indianapolis-to-quad-cities) - [Flights from Miami to Ohio River Valley](https://www.expedia.ca/lp/flights/178286/6233674/miami-to-ohio-river-valley) - [Flights from Minneapolis - St. Paul to Quad Cities](https://www.expedia.ca/lp/flights/178287/603001/minneapolis-st-paul-to-quad-cities) - [Flights from Minneapolis - St. Paul to Ohio River Valley](https://www.expedia.ca/lp/flights/178287/6233674/minneapolis-st-paul-to-ohio-river-valley) - [Flights from Orlando to Ohio River Valley](https://www.expedia.ca/lp/flights/178294/6233674/orlando-to-ohio-river-valley) - [Flights from Seattle to Quad Cities](https://www.expedia.ca/lp/flights/178307/603001/seattle-to-quad-cities) - [Flights from Toronto to Quad Cities](https://www.expedia.ca/lp/flights/178314/603001/toronto-to-quad-cities) - [Flights from Toronto to Ohio River Valley](https://www.expedia.ca/lp/flights/178314/6233674/toronto-to-ohio-river-valley) - [Flights from Vancouver to Ohio River Valley](https://www.expedia.ca/lp/flights/178315/6233674/vancouver-to-ohio-river-valley) - [Flights from Edmonton to Quad Cities](https://www.expedia.ca/lp/flights/180002/603001/edmonton-to-quad-cities) - [Flights from Edmonton to Ohio River Valley](https://www.expedia.ca/lp/flights/180002/6233674/edmonton-to-ohio-river-valley) - [Flights from Québec City to Ohio River Valley](https://www.expedia.ca/lp/flights/180017/6233674/quebec-city-to-ohio-river-valley) - [Flights from Amarillo to Quad Cities](https://www.expedia.ca/lp/flights/371/603001/amarillo-to-quad-cities) - [Flights from Hamilton to Quad Cities](https://www.expedia.ca/lp/flights/3963/603001/hamilton-to-quad-cities) - [Flights from Fort Lauderdale to Ohio River Valley](https://www.expedia.ca/lp/flights/601750/6233674/fort-lauderdale-to-ohio-river-valley) - [Flights from Newark to Ohio River Valley](https://www.expedia.ca/lp/flights/601760/6233674/newark-to-ohio-river-valley) - [Flights from Buffalo to Quad Cities](https://www.expedia.ca/lp/flights/602674/603001/buffalo-to-quad-cities) - [Flights from Buffalo to Ohio River Valley](https://www.expedia.ca/lp/flights/602674/6233674/buffalo-to-ohio-river-valley) - [Flights from Birmingham to Ohio River Valley](https://www.expedia.ca/lp/flights/602981/6233674/birmingham-to-ohio-river-valley) - [Flights from Quad Cities](https://www.expedia.ca/lp/flights/603001/flights-from-quad-cities) - [Flights from Winnipeg to Quad Cities](https://www.expedia.ca/lp/flights/6141041/603001/winnipeg-to-quad-cities) - [Flights from Ohio River Valley](https://www.expedia.ca/lp/flights/6233674/flights-from-ohio-river-valley) ### Packages - [Lake Michigan](https://www.expedia.ca/Lake-Michigan-United-States-of-America.d6338716.Vacation-Attraction) - [Visit Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley.dx6233674) - [Quad Cities Vacations](https://www.expedia.ca/Quad-Cities.d603001.Destination-Travel-Guides) - [Visit Quad Cities](https://www.expedia.ca/Quad-Cities.dx603001) - [Visit Southeast Iowa](https://www.expedia.ca/Southeast-Iowa.dx6234151) ### Cars - [Ace Rental Cars in Quad Cities](https://www.expedia.ca/Ace-Car-Rentals-In-Quad-Cities.d603001-c2.Car-Rental-Guide-Suppliers) - [Advantage Rent-A-Car Rental Cars in Ohio River Valley](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-Ohio-River-Valley.d6233674-c3.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Quad Cities](https://www.expedia.ca/Avis-Car-Rentals-In-Quad-Cities.d603001-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Quad Cities](https://www.expedia.ca/Car-Rentals-In-Quad-Cities.d603001.Car-Rental-Guide) - [Pickup Car Rentals in Ohio River Valley](https://www.expedia.ca/Pickup-Car-Rentals-In-Ohio-River-Valley.d6233674-tPickup.Car-Rental-Guide-Class) - [Thrifty Car Rental Rental Cars in Ohio River Valley](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Ohio-River-Valley.d6233674-c45.Car-Rental-Guide-Suppliers) ### Other - [Things to do in Quad Cities](https://www.expedia.ca/Things-To-Do-In-Quad-Cities.d603001.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)