
Western Suburbs 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 Western Suburbs
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,342, price is now CA $981 per person
CA $981
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too.
Reviewed on Jun 3, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,269, price is now CA $1,498 per person
CA $1,498
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026

Swissotel - Chicago
Downtown Chicago
Price was CA $1,690, price is now CA $1,156 per person
CA $1,156
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
Location is closer to
Navy pier. Not a lot of nice food options around.
Reviewed on Jun 3, 2026

The Emily Hotel
Downtown Chicago
Price was CA $1,843, price is now CA $1,268 per person
CA $1,268
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,739, price is now CA $1,236 per person
CA $1,236
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
The room itself was excellent — 9/10. The view was amazing, the bed was very comfortable, and the room was spacious and well-designed.
However, for the price and for a hotel that markets itself as a 4-star property, many amenities were disappointing.
First, the coffee machine in the room was very low quality, more comparable to what you would typically find at a Comfort Inn. There were also no bathrobes or hotel slippers provided, which I would expect at this price point.
The lobby was surprisingly small and not particularly inviting. It felt dark and lacked the atmosphere you would expect from a higher-end hotel.
The hotel only has one restaurant, and unfortunately the food quality was below average.
Another disappointment was the rooftop. The hotel advertises rooftop access, but the rooftop is not actually owned or operated by the hotel. During our stay, it was closed for a private event, making it unavailable to guests.
To make matters worse, on the day we checked out, the elevator was out of service, so we had to carry our luggage down the stairs ourselves.
Overall, I would rate the room 9/10, but the amenities, dining, and overall hotel experience only 2/10.
Because the room and view were truly outstanding, I would give the hotel an overall rating of 7/10. Without the exceptional room and view, my rating would have been significantly lower.
Reviewed on Jun 2, 2026
Don't see what you're looking for?
See all available trips from Columbus to Western Suburbs
View all trips5* Mountain holidays in Western Suburbs
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Price was CA $2,556, price is now CA $2,054 per person
CA $2,054
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
I truly enjoyed my 5 night stay at this hotel. Everyone was helpful, friendly, and accommodating. I love its location, near the Michael mile.
When I return to Chicago I will definitely stay at the Park Hyatt.
Reviewed on Apr 4, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,109, price is now CA $2,383 per person
CA $2,383
per person
Jul 12 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.
Reviewed on May 31, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,637, price is now CA $2,077 per person
CA $2,077
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Our third time at this hotel and still enjoying it.
Reviewed on May 30, 2026
Don't see what you're looking for?
See all available trips from Columbus to Western Suburbs
View all trips3 Night Mountain holidays in Western Suburbs
Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago
Downtown Chicago
Price was CA $1,285, price is now CA $929 per person
CA $929
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
Location is closer to
Navy pier. Not a lot of nice food options around.
Reviewed on Jun 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,650, price is now CA $1,185 per person
CA $1,185
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
The room itself was excellent — 9/10. The view was amazing, the bed was very comfortable, and the room was spacious and well-designed.
However, for the price and for a hotel that markets itself as a 4-star property, many amenities were disappointing.
First, the coffee machine in the room was very low quality, more comparable to what you would typically find at a Comfort Inn. There were also no bathrobes or hotel slippers provided, which I would expect at this price point.
The lobby was surprisingly small and not particularly inviting. It felt dark and lacked the atmosphere you would expect from a higher-end hotel.
The hotel only has one restaurant, and unfortunately the food quality was below average.
Another disappointment was the rooftop. The hotel advertises rooftop access, but the rooftop is not actually owned or operated by the hotel. During our stay, it was closed for a private event, making it unavailable to guests.
To make matters worse, on the day we checked out, the elevator was out of service, so we had to carry our luggage down the stairs ourselves.
Overall, I would rate the room 9/10, but the amenities, dining, and overall hotel experience only 2/10.
Because the room and view were truly outstanding, I would give the hotel an overall rating of 7/10. Without the exceptional room and view, my rating would have been significantly lower.
Reviewed on Jun 2, 2026

The Emily Hotel
Downtown Chicago
Price was CA $1,478, price is now CA $1,065 per person
CA $1,065
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026
Don't see what you're looking for?
See all available trips from Columbus to Western Suburbs
View all trips4 Night Mountain holidays in Western Suburbs
Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago
Downtown Chicago
Price was CA $1,690, price is now CA $1,156 per person
CA $1,156
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
Location is closer to
Navy pier. Not a lot of nice food options around.
Reviewed on Jun 3, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,269, price is now CA $1,498 per person
CA $1,498
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026

The Emily Hotel
Downtown Chicago
Price was CA $1,843, price is now CA $1,268 per person
CA $1,268
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026
Don't see what you're looking for?
See all available trips from Columbus to Western Suburbs
View all tripsMore 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.







