Historic Route 66 Mountain Holidays
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Top flight + Mountain hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was £1,866, price is now £1,513 per person
£1,513
per person
3 Aug - 7 Aug
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on 16 May 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £2,034, price is now £1,543 per person
£1,543
per person
30 Jul - 3 Aug
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
Ordered a high floor room and it didn't really seemed like a high floor. Overall, stay did it's job and the front desk staff is amazing! Hate that Everytime I went to the bar no one was available though.
Reviewed on 17 May 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was £1,941, price is now £1,559 per person
£1,559
per person
30 Jul - 3 Aug
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on 12 May 2026
The Emily Hotel
Downtown Chicago
Price was £1,918, price is now £1,566 per person
£1,566
per person
30 Jul - 3 Aug
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Staff was friendly, very nice property in a good walkable location
Reviewed on 1 May 2026
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was £1,963, price is now £1,603 per person
£1,603
per person
30 Jul - 3 Aug
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,091 reviews)
I would have really appreciated if there were a microwave available in our room.
Reviewed on 4 May 2026
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View all trips5* Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,710, price is now £1,389 per person
£1,389
per person
29 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Great hospitality!!! Will be back!
Thank you
Reviewed on 17 May 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was £1,973, price is now £1,704 per person
£1,704
per person
30 Jun - 5 Jul
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Este hotel están bastante bien situado cerca de tiendas sobre todo Bloomingdale que están en el mismo edificio es una buena opción
Reviewed on 18 May 2026
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See all available trips from London to Historic Route 66
View all trips3 Night Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was £1,149, price is now £993 per person
£993
per person
29 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (114 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on 17 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,710, price is now £1,389 per person
£1,389
per person
29 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Great hospitality!!! Will be back!
Thank you
Reviewed on 17 May 2026
Don't see what you're looking for?
See all available trips from London to Historic Route 66
View all trips4 Night Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was £1,928, price is now £1,387 per person
£1,387
per person
13 Jul - 17 Jul
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on 16 May 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £2,034, price is now £1,543 per person
£1,543
per person
30 Jul - 3 Aug
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
Ordered a high floor room and it didn't really seemed like a high floor. Overall, stay did it's job and the front desk staff is amazing! Hate that Everytime I went to the bar no one was available though.
Reviewed on 17 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £2,041, price is now £1,590 per person
£1,590
per person
13 Jul - 17 Jul
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Great hospitality!!! Will be back!
Thank you
Reviewed on 17 May 2026
Don't see what you're looking for?
See all available trips from Manchester to Historic Route 66
View all tripsMore holidays you might like
* 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.
