Historic Route 66 Golf Holidays

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Top flight + 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
£834
per person
26 Dec - 31 Dec
found 10 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,305
per person
26 Dec - 31 Dec
found 10 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff Centrally located on North River north bank. The room is big and spacious overlooking the river. We loved our stay. The concierge gave us a great tips and services Recommend by all means.

Reviewed on 2 Oct 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,057
per person
22 Nov - 29 Nov
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,703 reviews)
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,018
per person
22 Nov - 29 Nov
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (2,172 reviews)
Great location

Reviewed on 2 Oct 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
£1,068
per person
22 Nov - 29 Nov
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (3,324 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
£1,305
per person
26 Dec - 31 Dec
found 10 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff Centrally located on North River north bank. The room is big and spacious overlooking the river. We loved our stay. The concierge gave us a great tips and services Recommend by all means.

Reviewed on 2 Oct 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£1,742
per person
11 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
It was such a joy to stay at the Park Hyatt for our wedding! The staff at the Hyatt went above and beyond to make our stay memorable. It was all fabulous from the staff, to the food, to the beautiful views.

Reviewed on 1 Oct 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£2,092
per person
11 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Location, location, location.

Reviewed on 2 Oct 2026

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3 Night Golf holidays in Historic Route 66

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

Moonrise Hotel

Delmar Loop
£912
per person
19 Nov - 22 Nov
found 14 hours ago
Return direct flight included
London (LHR) to St. Louis (STL)
9/10 Wonderful! (2,026 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£2,008
per person
18 Nov - 21 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff Centrally located on North River north bank. The room is big and spacious overlooking the river. We loved our stay. The concierge gave us a great tips and services Recommend by all means.

Reviewed on 2 Oct 2026

The Cheshire

The Cheshire

£942
per person
19 Nov - 22 Nov
found 14 hours ago
Return direct flight included
London (LHR) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
It was one of the worst experiences I’ve ever had at a hotel, and I’ve wanted to stay at the Cheshire for years. Highly disappointed would not recommend the place was filthy.

Reviewed on 2 Oct 2026

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4 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
£1,083
per person
11 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,101
per person
11 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
great location, room and breakfast is very good and various

Reviewed on 2 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,376
per person
11 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff Centrally located on North River north bank. The room is big and spacious overlooking the river. We loved our stay. The concierge gave us a great tips and services Recommend by all means.

Reviewed on 2 Oct 2026

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Find amazing golf holidays in Historic Route 66

How can I find the best golf holidays in Historic Route 66?

Tee off your top golfing holiday in Historic Route 66 by searching for the perfect accommodation on Expedia. Pop in your dates and start looking at your options. You can even check and book flights, too – just don’t forget to include your golf bag as luggage!

Are there cheap golf packages available in Historic Route 66?

Bundling your accommodation, flights and car hire together is a great way to save money and ensure everything is easily organised. We have stacks of very tempting luxury and cheap golf packages, with those in Historic Route 66 starting from £834. Prices and availability are subject to change. Additional terms may apply.

Can I book Historic Route 66 golf and spa packages?

There’s no better way to unwind after a step-heavy day on the course than with a few hours in the spa. Or, for golf-widowed husbands or wives, a golf and spa package holiday could be a winning way to spend some quality time together, with activities to keep everyone happy. Use the spa filter to find golf holidays in Historic Route 66 with that added level of bliss.

How can I find luxury golf holidays in Historic Route 66?

Score under par on the course and go overboard on everything else with a luxury golf holiday to Historic Route 66. To find the most special spots, use the 5-star properties filter, and – go on – treat yourself to business class flights.

Can I book all-inclusive golf holidays in Historic Route 66?

Use the all-inclusive filter to hunt out those glorious all-inclusive golf holidays in Historic Route 66. If there are none available, consider half board – you’ll likely be out on the golf course at lunchtime anyway.

Why should I book Historic Route 66 golf holidays including flights?

Save money, save time and save paperwork by booking your accommodation, flights and even car hire all with Expedia. It takes just a few clicks to see all the options and book in one fell swoop.

Should I book a last-minute golf holiday in Historic Route 66?

If you have free time on your side or annual leave to use up, a spontaneous last-minute golf trip in Historic Route 66 is a wonderful idea. Pop in a few dates to see what’s available – you might even save money with last-minute deals.

Can I book a golf holiday in Historic Route 66 with free cancellation and/or flexible dates?

Flexibility is the spice of life, so use our dedicated filter to find accommodation and flights with free cancellation options. Remember, though, always check the small print before booking!

Why should I book my golf trip to Historic Route 66 with Expedia?

Booking a golf trip to Historic Route 66 with Expedia feels like getting a hole-in-one on your first shot on the course. It’s smooth, easy and, with so many options to choose from, you’ll feel giddy with excitement.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.