Rush Street Mountain Vacations
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Flight and Mountain hotel deals in Rush Street
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Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!
Reviewed on Aug. 18, 2025
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View all trips5* Mountain holidays in Rush Street
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View all trips3 Night Mountain holidays in Rush Street
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Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on Aug. 17, 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.
Reviewed on Aug. 17, 2025
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