Northwest Side Adventure Vacations
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Flight and Adventure hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,453, price is now CA $1,031 per person
CA $1,031
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.
Reviewed on Oct 26, 2026
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View all trips5* Adventure holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
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View all trips3 Night Adventure holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,453, price is now CA $1,031 per person
CA $1,031
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.
Reviewed on Oct 26, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips4 Night Adventure holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was CA $3,096, price is now CA $978 per person
CA $978
per person
Dec 20 - Dec 24
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
My experience at the Sheraton was terrible. I was assigned a room right next to the elevator, where there was also a shared microwave for guests on the floor. A large group of young people was placed in the same hallway. They appeared to be intoxicated and made excessive noise from around 11 p.m. until nearly 4 a.m., making it impossible to sleep.
I called the front desk three times asking for help, but the noise continued and nothing was resolved. I felt very unsafe and completely let down by the hotel staff.
Guests should be able to expect a restful stay and a response when they ask for help. I left exhausted and deeply disappointed. I expected much better from the Sheraton.
Reviewed on Oct 28, 2026
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View all tripsThings to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
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.
