
Central Chicago Scuba Diving Vacations
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Flight and Scuba Diving hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,602, price is now CA $1,142 per person
CA $1,142
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Great place to stay. Amazing hotel at reasonable price.
Reviewed on Jul 11, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,737, price is now CA $1,169 per person
CA $1,169
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The free breakfast was non-existent. Every time I went downstairs at 8am to get breakfast, there was only apples in a basket and coffee. No one comes to clean your room during the entire stay so trash is overflowing. The property is near everything so it’s walkable to nearby attractions which was nice.
Reviewed on Jul 10, 2026


Level Chicago – Old Town
Downtown Chicago
Price was CA $2,287, price is now CA $1,612 per person
CA $1,612
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,861, price is now CA $1,332 per person
CA $1,332
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
There were stains on the carpet and where the thermostat was an awful smell coming from that area-like musty smelling. We stayed and paid premium rate for a firework view and while I know they can’t control the weather, I reached out to see if they would be willing to credit something toward a future stay so we could enjoy the experience. Not even an acknowledgment of our disappointment or receipt of our email. Disappointed in the whole situation.
Reviewed on Jul 10, 2026
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View all trips5* Scuba Diving holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,535, price is now CA $1,968 per person
CA $1,968
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST
Reviewed on Jul 10, 2026

The Langham, Chicago
Downtown Chicago
Price was CA $3,181, price is now CA $2,523 per person
CA $2,523
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Fantastic staff, beautiful property. Highly recommend the club lounge
Reviewed on Jul 10, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,569, price is now CA $2,080 per person
CA $2,080
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026
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View all trips3 Night Scuba Diving holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,101, price is now CA $777 per person
CA $777
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The free breakfast was non-existent. Every time I went downstairs at 8am to get breakfast, there was only apples in a basket and coffee. No one comes to clean your room during the entire stay so trash is overflowing. The property is near everything so it’s walkable to nearby attractions which was nice.
Reviewed on Jul 10, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,822, price is now CA $1,326 per person
CA $1,326
per person
Oct 6 - Oct 9
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips4 Night Scuba Diving holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,602, price is now CA $1,142 per person
CA $1,142
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Great place to stay. Amazing hotel at reasonable price.
Reviewed on Jul 11, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,737, price is now CA $1,169 per person
CA $1,169
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The free breakfast was non-existent. Every time I went downstairs at 8am to get breakfast, there was only apples in a basket and coffee. No one comes to clean your room during the entire stay so trash is overflowing. The property is near everything so it’s walkable to nearby attractions which was nice.
Reviewed on Jul 10, 2026

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See all available trips from Columbus to Central Chicago
View all tripsThings to do

Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend

Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
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