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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) 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
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,855, price is now CA $1,161 per person
CA $1,161
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Clean room, gray lobby and nice bar with excellent bartender, breakfast was very good !
Reviewed on Mar 27, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,939, price is now CA $1,428 per person
CA $1,428
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) 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
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
Hotel Arista
Price was CA $1,425, price is now CA $1,058 per person
CA $1,058
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Our room was spacious, clean and well appointed. I love a bathroom with good lighting and the tv in the vanity mirror was fantastic to catch the morning news as we got ready!!
The staff was exceptional. From check in, to drinks at the bar, to room service, everyone was incredibly friendly and professional. I highly recommend Hotel Arista.
Reviewed on Mar 24, 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.
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 Southeast Side
Price found within the past 48 hours. Click for updated prices.
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 6 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
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,855, price is now CA $1,161 per person
CA $1,161
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Clean room, gray lobby and nice bar with excellent bartender, breakfast was very good !
Reviewed on Mar 27, 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
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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) 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
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)
Clean room, gray lobby and nice bar with excellent bartender, breakfast was very good !
Reviewed on Mar 27, 2026
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