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.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,069
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
👍

Reviewed on Sep 28, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,089
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
It was great great great !

Reviewed on Sep 28, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,083
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Wonderful rooms and great views

Reviewed on Sep 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,344
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go. There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable. We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles. Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult. The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.

Reviewed on Sep 28, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,130
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
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5* Golf holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,089
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
It was great great great !

Reviewed on Sep 28, 2026

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 $1,361
per person
Nov 12 - Nov 15
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Albuquerque (ABQ)
8.2/10 Very good! (1,001 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
CA $2,032
per person
Oct 29 - Nov 1
found 17 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
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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 $964
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,344
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go. There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable. We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles. Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult. The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.

Reviewed on Sep 28, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,130
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Historic Route 66
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4 Night Golf holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $991
per person
Dec 10 - Dec 14
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
👍

Reviewed on Sep 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,077
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go. There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable. We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles. Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult. The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.

Reviewed on Sep 28, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,889
per person
Dec 23 - Dec 27
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
It was great great great !

Reviewed on Sep 28, 2026

Don't see what you're looking for?
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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 $964, 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 27, 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.