Far Southeast Side Mountain Vacations
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Flight and Mountain hotel deals in Far Southeast 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 $1,395, price is now CA $997 per person
CA $997
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
To me the property is overrated! Front desk staff are not very approachable! I think that is what made my stay a little less enjoyable!
Reviewed on Nov 12, 2026
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View all trips5* Mountain holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was CA $2,945, price is now CA $1,976 per person
CA $1,976
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
i love it
Reviewed on Nov 10, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,256, price is now CA $2,339 per person
CA $2,339
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
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See all available trips from Columbus to Far Southeast Side
View all trips3 Night Mountain holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was CA $1,110, price is now CA $797 per person
CA $797
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
First time ever in Chicago and it was fabulous. The hotel was beautiful. Staff was friendly. We paid for the view and it was phenomenal. Definitely recommend.
Reviewed on Nov 12, 2026
Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all trips4 Night Mountain holidays in Far Southeast 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 $1,556, price is now CA $1,106 per person
CA $1,106
per person
Jan 29 - Feb 2
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
To me the property is overrated! Front desk staff are not very approachable! I think that is what made my stay a little less enjoyable!
Reviewed on Nov 12, 2026
Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all tripsThings to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
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.
