Far Southwest Side Mountain Vacations
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Flight and Mountain hotel deals in Far Southwest 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 $1,326, price is now CA $939 per person
CA $939
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Staff were awesome!! Room view was amazing . Only complaint if I had one would be we didn’t get our room turned over one of the days.
Reviewed on Mar 28, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,497, price is now CA $1,006 per person
CA $1,006
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
This is the best hotel I’ve been so far, their staffs were supper nice and their rooms are amazing, thanks
Reviewed on Mar 28, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,735, price is now CA $1,277 per person
CA $1,277
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
The Wade
Downtown Chicago
Price was CA $2,095, price is now CA $1,555 per person
CA $1,555
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Enjoyed our stay. Views were amazing and location convenient.
Reviewed on Mar 26, 2026
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View all trips5* Mountain holidays in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,456, price is now CA $1,939 per person
CA $1,939
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
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View all trips3 Night Mountain holidays in Far Southwest 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 $1,326, price is now CA $939 per person
CA $939
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Staff were awesome!! Room view was amazing . Only complaint if I had one would be we didn’t get our room turned over one of the days.
Reviewed on Mar 28, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,497, price is now CA $1,006 per person
CA $1,006
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
This is the best hotel I’ve been so far, their staffs were supper nice and their rooms are amazing, thanks
Reviewed on Mar 28, 2026
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,504, price is now CA $1,072 per person
CA $1,072
per person
Jun 19 - Jun 22
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (1,012 reviews)
Great views close to museums and great restaurants
Reviewed on Mar 27, 2026
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View all trips4 Night Mountain holidays in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,492, price is now CA $1,038 per person
CA $1,038
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
This is the best hotel I’ve been so far, their staffs were supper nice and their rooms are amazing, thanks
Reviewed on Mar 28, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,284, price is now CA $1,719 per person
CA $1,719
per person
Jun 18 - Jun 22
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing
Reviewed on Mar 27, 2026
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