Paw Paw 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 Paw Paw Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,139, price is now CA $746 per person
CA $746
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on Apr 24, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,836, price is now CA $1,194 per person
CA $1,194
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
A unique experience, loved being on the pier! Stunning views of the lake!
Reviewed on May 2, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,509, price is now CA $1,012 per person
CA $1,012
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Paw Paw Hotel Deals
Comfort Inn & Suites Rochelle - DeKalb
1133 N 7th St Rochelle IL
Fully refundable
The price is CA $103 per night from May 31 to Jun 1
CA $103
CA $114 total
May 31 - Jun 1
includes taxes & fees
8/10 Very Good! (490 reviews)
The staff is always very ki
Reviewed on Apr 17, 2026
Super 8 by Wyndham Rochelle
601 E Highway 38 Rochelle IL
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from May 10 to May 11
CA $89
CA $99 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (987 reviews)
did not have breakfast, but looking at it, it was very small and either out of things or not enough stock. I passed on it. The bathroom appeared to have NO light switch that I could find. Used the entry light to see, and didn't use the shower.
Reviewed on Apr 28, 2026
Super 8 by Wyndham DeKalb IL
800 W Fairview Dr DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from May 4 to May 5
CA $93
CA $105 total
May 4 - May 5
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.
