Central Chicago Mountain Vacations
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Flight and Mountain hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $2,146
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Loved the location. Was able to park in the parking ramp, leave the car, and walk to many, many places! Room was clean, view was excellent, and choices of food/snacks was endless!
Reviewed on Aug 18, 2026
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View all trips5* Mountain holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
CA $2,072
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
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View all trips3 Night Mountain holidays in Central Chicago
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View all trips4 Night Mountain holidays in Central Chicago
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Freehand Chicago
Downtown Chicago
CA $2,345
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (3,256 reviews)
Employees were wonderful and helpful, but the place could use a serious upgrade. Only one lamp worked in my room which left it very dark, especially because my window opened to a parking garage which meant I got no natural light. The bathroom is tiny and dark, and there’s no fridge or kettle in the room. It was hard to get ready for my day there. Very minimal place, probably won’t stay there again.
Reviewed on Aug 18, 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.
