Historic Route 66 Adults Only Holidays

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Top flight + Adults Only 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 17 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 17 hours ago
Return direct flight included
London (LON) 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
£1,057
per person
22 Nov - 29 Nov
found 1 day 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 1 day 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 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
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5* Adults Only 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 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
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)
Our room was exceptionally clean with all the amenities. And we were especially impressed by the staff - everyone was friendly and anxious to help. A most enjoyable stay. We look forward to the next! 46676

Reviewed on 3 Oct 2026

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3 Night Adults Only 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 22 hours ago
Return direct flight included
London (LHR) to St. Louis (STL)
9/10 Wonderful! (2,026 reviews)
The room could use a few more usb charging ports. But very nice

Reviewed on 2 Oct 2026

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)
The Cheshire

The Cheshire

£942
per person
19 Nov - 22 Nov
found 22 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 Adults Only 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)
Everything was awesome but there was no microwave and we needed one

Reviewed on 3 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)
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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.