Northwest Side Scuba Diving Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Flight and Scuba Diving hotel deals in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,008
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,192
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
This place was 10/10. The room was extremely clean. Had everything you needed. Even a washer and dryer. The staff were very helpful and friendly. They have a cute children’s area. The amenities floor was amazing and comfortable. Great area to walk to dinning and shopping and the oak st beach. We are walkers so while nothing was right around the corner we could walk to many sights like the river walk, the bean, chicago 360, all the stores.

Reviewed on Sep 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,032
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,224
per person
Nov 18 - Nov 21
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
CA $1,982
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
Amazing

Reviewed on Sep 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips

5* Scuba Diving holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,224
per person
Nov 18 - Nov 21
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
CA $1,982
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
Amazing

Reviewed on Sep 8, 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
CA $1,785
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Staff was excellent.

Reviewed on Sep 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips

3 Night Scuba Diving holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $788
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,224
per person
Nov 18 - Nov 21
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $891
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
This place was 10/10. The room was extremely clean. Had everything you needed. Even a washer and dryer. The staff were very helpful and friendly. They have a cute children’s area. The amenities floor was amazing and comfortable. Great area to walk to dinning and shopping and the oak st beach. We are walkers so while nothing was right around the corner we could walk to many sights like the river walk, the bean, chicago 360, all the stores.

Reviewed on Sep 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips

4 Night Scuba Diving holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
CA $752
per person
Nov 21 - Nov 25
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,321
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Had to request towels three times throughout the day before brought up. Thermostat stopped working, maintenance came and “fixed”, it stopped again in the middle of night spent a stuffy, hot night’s sleep. Shower drain clogged, informed front desk, maintenance never came that day. Glad we checked out the next day before anything else went wrong. Spend your $ somewhere else!

Reviewed on Sep 18, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

Downtown Chicago
Save 100% on your flight
CA $1,604
per person
Oct 18 - Oct 22
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,451 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

CA $39
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in Northwest Side

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.