Title: Golf Vacations in Historic Route 66 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 Golf 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 Golf hotel deals in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 $842 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago CA $1,223 per person Apr 2 - Apr 7 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) Staff was super friendly and rooms were clean. Definitely will come back Reviewed on Jan 20, 2026 ![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 $969 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) Hotel was very clean. Concierge was great with advice. Sports bar pepperoni pizza was great and the french fries were just as freshly cooked. Room was clean. Bed was great. Shower pressure great. Toilet correct height for a man of my age. Pillows…..pillows with a firmness of that of a 48 year old mother who breast fed all her 7 children until 9 months old. Glad the kids are good but those pillows need work Hilton. God Bless and safe travels to all. See you next time. Reviewed on Jan 20, 2026 ![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 $1,154 per person Apr 7 - Apr 14 found 2 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 8.8/10 Excellent! (1,001 reviews) Always fun to stay in a different room at The Vanessie. The staff is super friendly and rooms are nicely finished. The breakfast menu is always delicious and the cook is cheerful with a nice smile. We love staying there on our way to AZ. Highly recommend!! Reviewed on Jan 12, 2026 ![Hotel Santa Fe](https://images.trvl-media.com/lodging/1000000/20000/19400/19360/1968861c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Santa Fe Downtown Santa Fe CA $1,360 per person Apr 7 - Apr 14 found 2 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 9.2/10 Wonderful! (1,055 reviews) My husband ordered a breakfast but the muffin wasn’t Reviewed on Jan 20, 2026 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/2026-02-21/2026-02-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Golf holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $878 per person Feb 25 - Feb 27 found 1 day ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on Jan 4, 2026 ![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 $2,211 per person Mar 25 - Apr 1 found 16 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 2026 ![Bishop's Lodge, Auberge Collection](https://images.trvl-media.com/lodging/1000000/50000/40800/40737/dc73db0b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bishop's Lodge, Auberge Collection Tesuque CA $4,708 per person Apr 7 - Apr 14 found 2 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 9.4/10 Exceptional! (87 reviews) Everyone was so kind and attentive and the rooms and grounds were so beautiful and clean. Reviewed on Jan 9, 2026 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/2026-02-21/2026-02-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Golf holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 $752 per person Apr 17 - Apr 20 found 18 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 ![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 $1,521 per person Mar 12 - Mar 15 found 1 day ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 2026 ![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 $1,173 per person Apr 17 - Apr 20 found 18 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on Jan 20, 2026 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/2026-02-21/2026-02-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Golf holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 $842 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $1,069 per person Apr 2 - Apr 6 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all. Reviewed on Jan 20, 2026 ![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/800a6847_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wildwood Hotel CA $1,002 per person Mar 18 - Mar 22 found 1 hour ago Roundtrip flight included Toronto (YYZ) to St. Louis (STL) 9.2/10 Wonderful! (1,600 reviews) Room was clean and big with a separate sitting area. We would definitely stay there again . Reviewed on Jan 21, 2026 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/2026-02-21/2026-02-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Discover the ultimate golf vacation from Historic Route 66 with Expedia #### What are some benefits when booking golf vacations from Historic Route 66? Booking a golf vacation means putting golf at the centre of your entire experience. Not only will you be able to enjoy easy access to the greens, but you'll often have access to all the equipment you need as well. Plus, golf stays tend to be on the more luxurious end of the spectrum, so you're likely to have some other high-end amenities as well. #### How can I find the best golf vacations in Historic Route 66? The best way to find golf vacations in Historic Route 66 is to take advantage of numerous search filters. You can look for golf stays specifically, with additional filters available for certain courses in some destinations. Plus, if you travel during the off-season in , you may even be able to get high-end stays at a discount. #### Are there cheap golf packages available? Yes, you'll find prices as low as CA $752, but the overall price depends on several factors. The time of year you travel to Historic Route 66 and the amenities you opt for can play a role in the cost of your package. Some package deals offer discounts of up to 25, but that's just a general trend rather than a guarantee. #### Can I book golf and spa vacation packages? Golf is often considered a luxury activity, so it's only natural that it be paired with other high-end experiences. You can implement the spa filter to sort for properties that have spa facilities, which can be especially useful for resting and rejuvenating in between games. #### How can I find luxury golf vacations in Historic Route 66? A lot of golf vacations are already luxurious given the nature of the game, but there are a few things you can do to push it as far as it can go. Use search filters to highlight only 5-star properties to ensure you're getting the best of the best. Business-class flights are available as well in most cases. #### Can I book an all-inclusive golf vacation in Historic Route 66? In many cases, yes. There's even a search filter for all-inclusivity, so you can sort for all-inclusive stays specifically. Even when an all-inclusive experience that matches your needs isn't available, you may be able to find some half-board options. This is also one of the best ways to find luxury golf vacations. #### Why should I book golf packages including flights? When you book your flight and your accommodations together, you can enjoy some serious savings compared to what you'd find booking separately. We're your one-stop shop for all your travel needs, and convenience is just the beginning when booking golf vacations from Historic Route 66 with us. #### Should I book a last-minute golf vacation? Booking last-minute to Historic Route 66 shouldn't be your first choice, but if you like to travel spontaneously, there are a few benefits to enjoy. Occasionally, you may be able to save money by booking last-minute, as accommodations are interested in filling their last few vacancies as fast as they can. The deals aren't guaranteed, however, so keep that in mind when planning. Sometimes, accommodations will simply be sold out. #### Can I book a golf vacation that is fully refundable? Yes, you'll find several options that are fully refundable among our packages in Historic Route 66\. You can even filter for fully refundable stays specifically. Just remember to check out each accommodation's policy specifically to make sure your booking qualifies. #### Why should I book my golf trip with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel needs. You can search through a massive collection of packages and potentially unlock discounts by booking your flight and accommodations together. Even more discounts may be available for Expedia Rewards members, such as special deals and the ability to earn points to put toward discounts on future bookings. ## 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 Golf Vacation Destinations > - [Golf vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/117/Mexico) > - [Golf vacations Myrtle Beach ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/601685/Myrtle-Beach) > - [Golf vacations in Portugal ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/147/Portugal) > - [Golf vacations in Thailand ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/178/Thailand) > - [Golf vacations in Belek ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6034717/Belek) > - [Golf vacations in Las Vegas ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/178276/Las-Vegas) > - [Golf vacations in Scotland ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/11219/Scotland) > - [Golf vacations in Tenerife ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6047194/Tenerife) > - [Golf vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6022969/Caribbean) > - [Golf vacations in Lanzarote ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/282/Lanzarote) > - [Golf vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/86/Italy) > - [Golf vacations in Turkey ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/183/Turkey) > - [Golf vacations in Vilamoura ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/11395/Vilamoura) > - [Golf vacations in Ireland ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/84/Ireland) > - [Golf vacations in the Dominican Republic ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/50/Dominican-Republic) > - [Golf vacations in the United Kingdom ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/190/United-Kingdom) > - [Golf vacations in Hawaii ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/213/Hawaii) > - [Golf vacations in Algarve ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/182215/Algarve) > - [Golf vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/45/Cyprus) ## 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