Title: All inclusive Vacations in Historic Route 66 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Route 66 All inclusive Vacations ## 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 ## Flight and All inclusive hotel deals in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago CA $783 per person Jan 22 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,002 reviews) Amazing location. Love this historic hotel and the included room service breakfast is one of the best I’ve ever had. Reviewed on Dec 8, 2025 ![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 $1,242 per person Jan 22 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on Dec 2, 2025 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $833 per person Jan 22 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on Dec 3, 2025 ![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 $1,334 per person Feb 14 - Feb 21 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Albuquerque (ABQ) 8.8/10 Excellent! (1,001 reviews) This was our first time staying at this property. We were completely blown away. Our room was spacious, cozy and had an amazing bathroom. Breakfast was a very nice touch in the morning. Good food! We will be staying here again! Reviewed on Dec 7, 2025 ![The Hacienda & Spa at Hotel Santa Fe](https://images.trvl-media.com/lodging/1000000/810000/802700/802697/f0a24cfb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hacienda & Spa at Hotel Santa Fe Downtown Santa Fe CA $1,990 per person Feb 22 - Mar 1 found 11 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 9.4/10 Exceptional! (989 reviews) Best hotel ever! Gorgeous property. First-class from check in, to happy hour, to dinner, to rooms, to linens, to personnel and staff! Awesome experience all the way around! Highly recommend and will definitely return! Reviewed on Dec 4, 2025 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 $1,242 per person Jan 22 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on Dec 2, 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,660 per person Jan 29 - Feb 2 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 ![Four Seasons Resort Rancho Encantado Santa Fe](https://images.trvl-media.com/lodging/1000000/50000/40800/40731/eb9982cf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Resort Rancho Encantado Santa Fe CA $3,470 per person Jan 18 - Jan 25 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 9.4/10 Exceptional! (264 reviews) Would not recommend this property given the price - poorly managed, grounds are weedy and unkept, no sundry store, no service after 10pm and the pool deck is lackluster. Casitas are very nice and housekeeping was very responsive. Stay at the Bishop’s Lodge - beautiful property with excellent staff. Reviewed on Aug 11, 2025 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $513 per person Feb 20 - Feb 23 found 16 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,229 reviews) Wonderful staff. Very friendly and knowledgeable about local events and recommendations for entertainment. Property was clean at all times and walkable even during inclement weather conditions. I would definitely return. Reviewed on Dec 7, 2025 ![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 $875 per person Feb 13 - Feb 16 found 14 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on Dec 2, 2025 ![Sandia Resort And Casino](https://images.trvl-media.com/lodging/2000000/1550000/1540100/1540099/06593b7d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sandia Resort And Casino Northeast Heights CA $963 per person Feb 10 - Feb 13 found 10 hours ago Roundtrip flight included Vancouver (YVR) to Albuquerque (ABQ) 9.4/10 Exceptional! (1,304 reviews) Room was nice and comfy! Bathroom was really nice! Nice weekend getaway! Reviewed on Dec 4, 2025 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare CA $897 per person Jan 29 - Feb 2 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly. Reviewed on Dec 6, 2025 ![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 $1,385 per person Jan 27 - Jan 31 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on Dec 2, 2025 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $1,175 per person Jan 27 - Jan 31 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Embark on an unforgettable all-inclusive trip to Historic Route 66 including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Historic Route 66, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget. #### Can I book all-inclusive packages with airfare and meals? Yes, all-inclusive vacation packages are readily available for Historic Route 66, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 34\. #### Why should I book Historic Route 66 vacations that are all inclusive and adults only? Adults-only stays in Historic Route 66 are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find. #### Can I book all-inclusive packages? Yes, all-inclusive packages are fairly standard in Historic Route 66\. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive. #### Can I book cheap all-inclusive trips to Historic Route 66? If you're looking to save, you'll find a wide range of prices available, ranging from CA $513\. By booking your accommodations and flight together, you may be able to enjoy savings of up to 34\. Be sure to sort your search results by price to list the cheapest options first. #### What should I look for when booking a 5-star all-inclusive vacation in Historic Route 66? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Historic Route 66, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group. #### What should I consider when booking Historic Route 66 vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Historic Route 66 is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying Historic Route 66's nightlife. #### How can I find the best deals on all-inclusive vacations in Historic Route 66? You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters. #### Can I book an all-inclusive package that is fully refundable? Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify. #### Why should I book an all-inclusive vacation with Expedia? Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts. ## More vacations you might like ![](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) ### Top All inclusive Vacation Destinations > - 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[All inclusive vacations in the Dominican Republic ](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) ## More Vacations Ideas [Flights to Historic Route 66 ](https://expedia.ca/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[ Historic Route 66 Hotels ](https://expedia.ca/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[ Historic Route 66 Vacation Rentals ](https://expedia.ca/Historic-Route-66-Vacation-Rentals.d702654640613646336.Travel-Guide-VacationRentals)[ Historic Route 66 Car Rentals ](https://expedia.ca/Car-Rentals-In-Historic-Route-66.d702654640613646336.Car-Rental-Guide)[ Historic Route 66 Vacations ](https://expedia.ca/Historic-Route-66.d702654640613646336.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app