Historic Route 66 Golf Vacations

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Flight and Golf hotel deals in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $837
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
Save 100% on your flight
CA $1,444
per person
Dec 13 - Dec 19
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,156 reviews)
Awesome stay and great location!

Reviewed on Oct 4, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,403
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
CA $1,078
per person
Dec 13 - Dec 19
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,703 reviews)
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago
CA $953
per person
Dec 13 - Dec 19
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8/10 Very good! (2,300 reviews)
they over booked the hotel for my night that I was staying, so they did not have a room for me when I got to the hotel

Reviewed on Oct 4, 2026

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5* Golf holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
CA $1,258
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (936 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,403
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa by Marriott

La Posada de Santa Fe, A Tribute Portfolio Resort & Spa by Marriott

Historic Eastside
CA $2,494
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albuquerque (ABQ)
8.2/10 Very good! (1,001 reviews)
Historic building in a great location close to town. Amazing staff who went out of their way to accommodate us. Restaurant food was excellent. Weekly complimentary happy hours were unexpected. Unfortunately the pool and hot tub were not available for several days due to a water malfunction. There are several types of rooms. Make sure you know what you are booking. We were not satisfied with the first room we had but the staff found us a much better room and graciously moved us as soon as they could.

Reviewed on Oct 1, 2026

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3 Night Golf holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $837
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,403
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,093
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,156 reviews)
Awesome stay and great location!

Reviewed on Oct 4, 2026

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4 Night Golf holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,067
per person
Dec 23 - Dec 27
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
It's our second time staying at the RIU and it's always an amazing experience. The staff is amazing, the cleanliness, the food, the overall experience of staying at the RIU is amazing. Thank you all for the wonderful experience!

Reviewed on Oct 4, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
CA $1,299
per person
Nov 12 - Nov 16
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $2,107
per person
Nov 10 - Nov 14
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
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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 $837, 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.