Hillsdale Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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 Hillsdale Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,667, price is now CA $1,255 per person
CA $1,255
per person
Apr 28 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special!
Reviewed on Mar 16, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,263, price is now CA $1,452 per person
CA $1,452
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.
Reviewed on Mar 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,331, price is now CA $1,504 per person
CA $1,504
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great location, views, & amenities.
Reviewed on Mar 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,717, price is now CA $1,289 per person
CA $1,289
per person
Jun 5 - Jun 8
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
Hilton Garden Inn Chicago Central Loop
Downtown Chicago
Price was CA $1,928, price is now CA $1,458 per person
CA $1,458
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,300 reviews)
It was a good place to spend a staycation weekend. Well located and friendly staff
Reviewed on Mar 16, 2026
Hillsdale Hotel Deals
Wyndham Moline on John Deere Commons
1415 River Dr Moline IL
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Apr 1 to Apr 2
CA $125
CA $141 total
Apr 1 - Apr 2
includes taxes & fees
9/10 Wonderful! (1,235 reviews)
Yes it’s a great location
Reviewed on Mar 20, 2026
DoubleTree by Hilton Davenport
111 E 2nd St Davenport IA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Mar 22 to Mar 23
CA $123
CA $137 total
Mar 22 - Mar 23
includes taxes & fees
7.6/10 Good! (1,003 reviews)
Rooms could be tidier especially shower
Reviewed on Mar 21, 2026
Hotel Blackhawk, Autograph Collection
200 E 3rd St Davenport IA
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Apr 2 to Apr 3
CA $209
CA $234 total
Apr 2 - Apr 3
includes taxes & fees
9.2/10 Wonderful! (923 reviews)
Just lovey
Reviewed on Mar 20, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
