
Historic Route 66 Scuba Diving Holidays
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Top flight + Scuba Diving hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.



Hotel Riu Plaza Chicago
Downtown Chicago
£1,111
per person
3 Nov - 10 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on 26 Aug 2026


Swissotel - Chicago
Downtown Chicago
£1,152
per person
3 Nov - 10 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on 26 Aug 2026
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Four Seasons Hotel Chicago
Downtown Chicago
£1,813
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on 23 Aug 2026

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View all trips3 Night Scuba Diving holidays in Historic Route 66
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Four Seasons Hotel Chicago
Downtown Chicago
£1,813
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on 23 Aug 2026

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View all trips4 Night Scuba Diving holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
£1,297
per person
21 Oct - 25 Oct
found 1 day ago
Return flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on 26 Aug 2026

Swissotel - Chicago
Downtown Chicago
£1,368
per person
21 Oct - 25 Oct
found 1 day ago
Return flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on 26 Aug 2026

Hotel Chicago Downtown, Autograph Collection by Marriott
Downtown Chicago
£2,207
per person
8 Oct - 12 Oct
found 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,016 reviews)
I always enjoy staying at this hotel. The staff are friendly, its right on the river, everything is very clean, hotel bar area is always a vibe, they offer freebies and discounts on food/drinks/entertainment, and there are so many restaurants within a few feet.
Reviewed on 27 Aug 2026
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View all trips* 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.










