Hooppole Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Hooppole Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,416, price is now CA $928 per person
CA $928
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on Apr 25, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,780, price is now CA $1,054 per person
CA $1,054
per person
Jul 17 - Jul 21
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,882 reviews)
The HVAC was annoying AF. It would go on and blow cold air for 10 minutes, then be off for 15-20 minutes repeatedly. It is so loud, it kept waking me up through out the night. As a short person, I did not like the fact the bed was a challenge to get on top. Not everyone is five feet tall.
Reviewed on Apr 26, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,447, price is now CA $941 per person
CA $941
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.
Reviewed on Apr 27, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,140, price is now CA $1,398 per person
CA $1,398
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
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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.
