Central Chicago Adventure Vacations
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Flight and Adventure hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,043, price is now CA $655 per person
CA $655
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
This hotel was lovely. The room was large and smelled divine. Everything was spotless, beds were comfy, location was excellent, staff were friendly and accommodating. Would definitely stay here again. :)
Reviewed on Sep. 4, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,667, price is now CA $1,008 per person
CA $1,008
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $3,378, price is now CA $2,120 per person
CA $2,120
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
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View all trips5* Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,667, price is now CA $1,008 per person
CA $1,008
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
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See all available trips from Columbus to Central Chicago
View all trips3 Night Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $770, price is now CA $485 per person
CA $485
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
loved our stay, great hotel and friendly staff
Reviewed on Sep. 3, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,667, price is now CA $1,008 per person
CA $1,008
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
Pendry Chicago
Downtown Chicago
Price was CA $1,043, price is now CA $655 per person
CA $655
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
This hotel was lovely. The room was large and smelled divine. Everything was spotless, beds were comfy, location was excellent, staff were friendly and accommodating. Would definitely stay here again. :)
Reviewed on Sep. 4, 2025
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See all available trips from Columbus to Central Chicago
View all trips4 Night Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston
Downtown Evanston
Price was CA $1,727, price is now CA $1,068 per person
CA $1,068
per person
Oct 10 - Oct 14
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!
Reviewed on Aug. 18, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,347, price is now CA $1,437 per person
CA $1,437
per person
Oct 6 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,772, price is now CA $1,112 per person
CA $1,112
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025
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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.