
Historic Route 66 Waterpark Vacations
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Flight and Waterpark hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,069, price is now CA $664 per person
CA $664
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Modern comfortable hotel in a good location close to downtown parks and museums Friendly helpful staff
Many good restaurants nearby
Reviewed on Aug. 19, 2025

Park Hyatt Chicago
Downtown Chicago
Price was CA $3,871, price is now CA $2,284 per person
CA $2,284
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,354, price is now CA $817 per person
CA $817
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on Aug. 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,851, price is now CA $1,121 per person
CA $1,121
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025

The Inn at Vanessie
Downtown Santa Fe
Price was CA $1,600, price is now CA $998 per person
CA $998
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Albuquerque (ABQ)
8.8/10 Excellent! (1,000 reviews)
Just a note that the stained glass-look contact paper on the windows is peeling off! Otherwise the room was quite clean and very comfortable.
Reviewed on Aug. 19, 2025
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View all trips5* Waterpark holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.


Park Hyatt Chicago
Downtown Chicago
Price was CA $3,871, price is now CA $2,284 per person
CA $2,284
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,851, price is now CA $1,121 per person
CA $1,121
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025
Don't see what you're looking for?
See all available trips from Columbus to Historic Route 66
View all trips3 Night Waterpark holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,354, price is now CA $817 per person
CA $817
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on Aug. 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,851, price is now CA $1,121 per person
CA $1,121
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025

Park Hyatt Chicago
Downtown Chicago
Price was CA $1,656, price is now CA $1,018 per person
CA $1,018
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025
Don't see what you're looking for?
See all available trips from Columbus to Historic Route 66
View all trips4 Night Waterpark holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Price was CA $2,804, price is now CA $1,634 per person
CA $1,634
per person
Oct 20 - Oct 24
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $2,865, price is now CA $1,748 per person
CA $1,748
per person
Oct 9 - Oct 13
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!
Reviewed on Aug. 18, 2025

The Langham, Chicago
Downtown Chicago
Price was CA $3,125, price is now CA $1,932 per person
CA $1,932
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
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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.