Historic Route 66 Scuba Diving Vacations
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Flight and Scuba Diving hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,775, price is now CA $1,201 per person
CA $1,201
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $3,272, price is now CA $2,122 per person
CA $2,122
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago
Reviewed on Apr 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,647, price is now CA $1,868 per person
CA $1,868
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay
Reviewed on Apr 7, 2026
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $2,134, price is now CA $1,509 per person
CA $1,509
per person
Jun 19 - Jun 23
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,202, price is now CA $2,322 per person
CA $2,322
per person
May 31 - Jun 3
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
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View all trips5* Scuba Diving 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 CA $2,437, price is now CA $1,887 per person
CA $1,887
per person
May 31 - Jun 3
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,202, price is now CA $2,322 per person
CA $2,322
per person
May 31 - Jun 3
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $2,847, price is now CA $2,069 per person
CA $2,069
per person
May 31 - Jun 3
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
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View all trips3 Night Scuba Diving holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,397, price is now CA $992 per person
CA $992
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,863, price is now CA $1,907 per person
CA $1,907
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay
Reviewed on Apr 7, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,775, price is now CA $1,201 per person
CA $1,201
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
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See all available trips from Columbus to Historic Route 66
View all trips4 Night Scuba Diving holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,735, price is now CA $1,101 per person
CA $1,101
per person
Jun 18 - Jun 22
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago
Reviewed on Apr 10, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $3,304, price is now CA $2,126 per person
CA $2,126
per person
Jun 19 - Jun 23
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
Clean nice view enjoyed my stay
Reviewed on Apr 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,143, price is now CA $1,392 per person
CA $1,392
per person
Jun 18 - Jun 22
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay
Reviewed on Apr 7, 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.
