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.
Swissotel - Chicago
Downtown Chicago
CA $844
per person
Oct 30 - Nov 1
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on Aug 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,950
per person
Nov 5 - Nov 8
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on Aug 23, 2026
5* Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,950
per person
Nov 5 - Nov 8
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on Aug 23, 2026
3 Night Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,950
per person
Nov 5 - Nov 8
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on Aug 23, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,800
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on Aug 26, 2026
4 Night Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,548
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on Aug 26, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,784
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on Aug 26, 2026
Things 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
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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.
