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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,100, price is now £2,408 per person
£2,408
per person
5 Jun - 12 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on 7 Apr 2026
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View all trips5* Adults Only holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,100, price is now £2,408 per person
£2,408
per person
5 Jun - 12 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on 7 Apr 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was £2,388, price is now £1,997 per person
£1,997
per person
28 Jun - 5 Jul
found 2 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on 6 Apr 2026
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View all trips3 Night Adults Only holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was £1,546, price is now £1,315 per person
£1,315
per person
28 May - 31 May
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Overall we enjoyed our stay. A few things that we didn’t care for. One is that the parking was inconvenient due to you having to call to get in every time you leave. Next would be the closet with the furnace was extremely noisy and almost kinda sounding. It came off and on very frequently. Lastly, the bed was as hard as a rock. If you are used a nice bed you can forget it. For the price no thx.
Reviewed on 12 Apr 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was £2,107, price is now £1,821 per person
£1,821
per person
28 May - 31 May
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
This is the best hotel on Michigan Avenue. Access to Nordstrom without leaving the building. Great views, food, very clean and smells amazing!
Reviewed on 11 Apr 2026
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View all trips4 Night Adults Only holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was £1,406, price is now £1,100 per person
£1,100
per person
27 Jun - 1 Jul
found 13 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Overall we enjoyed our stay. A few things that we didn’t care for. One is that the parking was inconvenient due to you having to call to get in every time you leave. Next would be the closet with the furnace was extremely noisy and almost kinda sounding. It came off and on very frequently. Lastly, the bed was as hard as a rock. If you are used a nice bed you can forget it. For the price no thx.
Reviewed on 12 Apr 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,709, price is now £1,293 per person
£1,293
per person
27 Jun - 1 Jul
found 13 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included
Reviewed on 12 Apr 2026
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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.
