Northwest Side Mountain Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Mountain hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
CA $1,405
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful stay along the riverwalk. Pretty easy to get to public transportation as well as much to do within walking distance. The hotel was clean and well taken care of. We enjoyed to larger gym hotel with plenty of equipment.
Reviewed on Aug 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,370
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Overall the views were wonderful. The proximity was great. The room wasn’t clean. Bedding had stains on it. No one cleaned our room. No towels. Front desk was definitely not friendly. The elevator stopped working.
Reviewed on Aug 11, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips5* Mountain holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips3 Night Mountain holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,945
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Overall the views were wonderful. The proximity was great. The room wasn’t clean. Bedding had stains on it. No one cleaned our room. No towels. Front desk was definitely not friendly. The elevator stopped working.
Reviewed on Aug 11, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips4 Night Mountain holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
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.
