Chicago Scuba Diving Vacations
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Flight and Scuba Diving hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,584, price is now CA $1,066 per person
CA $1,066
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.
Reviewed on May 14, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $2,052, price is now CA $1,266 per person
CA $1,266
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
It’s my favorite hotel always clean smell good and river walk across the street and all the staff always very helpful
Reviewed on May 15, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,145, price is now CA $1,440 per person
CA $1,440
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
Amazing hotel. I would stay again.
Reviewed on May 15, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,809, price is now CA $1,239 per person
CA $1,239
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on May 12, 2026
5* Scuba Diving holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,772, price is now CA $1,991 per person
CA $1,991
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!
Reviewed on May 13, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,694, price is now CA $2,975 per person
CA $2,975
per person
Jun 27 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
3 Night Scuba Diving holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,349, price is now CA $913 per person
CA $913
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
It’s my favorite hotel always clean smell good and river walk across the street and all the staff always very helpful
Reviewed on May 15, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,584, price is now CA $1,066 per person
CA $1,066
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.
Reviewed on May 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,544, price is now CA $1,069 per person
CA $1,069
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
Amazing hotel. I would stay again.
Reviewed on May 15, 2026
4 Night Scuba Diving holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $2,052, price is now CA $1,266 per person
CA $1,266
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
It’s my favorite hotel always clean smell good and river walk across the street and all the staff always very helpful
Reviewed on May 15, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,145, price is now CA $1,440 per person
CA $1,440
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
Amazing hotel. I would stay again.
Reviewed on May 15, 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.
