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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,001
per person
Sep 21 - Sep 23
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The service and rooms were excellent. Beds were comfortable and views were to die for. The food at Terra16 was a good but the wait times and food service took to long. Our fruit platter took over a half hour for breakfast. The spa was nice, but the lockers were hard to use or some worked and some did not lock. Front desk was exceptional and property was gorgeous. I would definitely stay again and was very happy with the staff who generally were attentive and kind.
Reviewed on Aug 13, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,424
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,398
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Rooms were decent. The view was the best part. Overall was alright, wouldn’t say the best experience.
Reviewed on Aug 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
CA $1,001
per person
Sep 21 - Sep 23
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The service and rooms were excellent. Beds were comfortable and views were to die for. The food at Terra16 was a good but the wait times and food service took to long. Our fruit platter took over a half hour for breakfast. The spa was nice, but the lockers were hard to use or some worked and some did not lock. Front desk was exceptional and property was gorgeous. I would definitely stay again and was very happy with the staff who generally were attentive and kind.
Reviewed on Aug 13, 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.
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View all trips4 Night Mountain holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
CA $809
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
The room was very clean for a less fancy city hotel. Staff was also super friendly. We arrived early and they were kind enough to hold our luggage while we explored.
Reviewed on Aug 13, 2026
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View all tripsThings 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.
