South Side Mountain Vacations
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Flight and Mountain hotel deals in South Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Price was CA $1,743, price is now CA $1,186 per person
CA $1,186
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,011 reviews)
Communication with staff/host 10/10 place clean felt safe would definitely stay again definitely worth it
Reviewed on Jun 6, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,306, price is now CA $1,594 per person
CA $1,594
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,498, price is now CA $2,522 per person
CA $2,522
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on Jun 6, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,936, price is now CA $1,401 per person
CA $1,401
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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 – Old Town
Downtown Chicago
Price was CA $1,876, price is now CA $1,378 per person
CA $1,378
per person
Aug 7 - Aug 10
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on Jun 3, 2026
5* Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,498, price is now CA $2,522 per person
CA $2,522
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on Jun 6, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,636, price is now CA $2,903 per person
CA $2,903
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,000 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
The Peninsula Chicago
Downtown Chicago
Price was CA $4,074, price is now CA $3,330 per person
CA $3,330
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everyone was so helpful and friendly
Great environment.
Cleaning, room service ,breakfast A+
Reviewed on May 29, 2026
3 Night Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Price was CA $1,743, price is now CA $1,186 per person
CA $1,186
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,011 reviews)
Communication with staff/host 10/10 place clean felt safe would definitely stay again definitely worth it
Reviewed on Jun 6, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,876, price is now CA $1,378 per person
CA $1,378
per person
Aug 7 - Aug 10
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on Jun 3, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,774, price is now CA $1,311 per person
CA $1,311
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
Really loved the gym facilities and brand new peloton equipment, room was very nice just small same with the lobby and cafe amenities but the staff was great
Reviewed on Jun 6, 2026
4 Night Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,773, price is now CA $1,299 per person
CA $1,299
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.
Reviewed on Jun 4, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,879, price is now CA $1,326 per person
CA $1,326
per person
Jul 11 - Jul 15
found 23 hours ago
Roundtrip flight included
Toronto (YTO) 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
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,026, price is now CA $1,452 per person
CA $1,452
per person
Jul 11 - Jul 15
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on Jun 3, 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.
