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.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,526, price is now CA $1,069 per person
CA $1,069
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,916, price is now CA $1,246 per person
CA $1,246
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Hard to find the parking . Everything at navy pier closes at 8pm . Staff offered no extras even though it says we are vip Expedia and hiltons honors .
Reviewed on Apr 17, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $2,226, price is now CA $1,481 per person
CA $1,481
per person
May 26 - May 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (2,120 reviews)
The stay was pleasant.
Reviewed on Apr 19, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,293, price is now CA $1,570 per person
CA $1,570
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
The Langham is simply unparalleled! The staff, the amenities, the location, food and level of service are at such a high level, I find it unmatched anywhere else. Simply cannot wait to come back
I actually came to Chicago to see a concert, I had bought the tickets and the air travel and knew I was going to stay at the Langham but FORGOT to reserve the room! The staff worked with me for 1/2 an hour to shoehorn me into the almost capacity hotel for 2 nights! Amazong
Reviewed on Apr 18, 2026
Hillsdale Hotel Deals
La Quinta Inn by Wyndham Davenport & Conference Center
3330 E Kimberly Rd Davenport IA
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Apr 30 to May 1
CA $88
CA $98 total
Apr 30 - May 1
includes taxes & fees
7.2/10 Good! (1,004 reviews)
Room was pretty clean, top sheet over the comforter needs to be thrown out. It was very stained. Bathroom only offered shampoo and the shower faucet needed to come with instructions. Twist left, then jimmy and shake to the right while pulling out. 😉 It was a nice stay for a quick cheap hotel.
Reviewed on Apr 14, 2026
Wyndham Moline on John Deere Commons
1415 River Dr Moline IL
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Apr 30 to May 1
CA $133
CA $150 total
Apr 30 - May 1
includes taxes & fees
9/10 Wonderful! (1,234 reviews)
The staff was VERY accommodating. The hotel was very clean and welcoming. The ONLY downfall was a small parking lot that had overflow. There was a game one night and parking was tough. Loved that it was right on the river and you could walk it. Walking distance to many places to eat. Loved this ...
Reviewed on Apr 19, 2026
DoubleTree by Hilton Davenport
111 E 2nd St Davenport IA
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Apr 26 to Apr 27
CA $136
CA $152 total
Apr 26 - Apr 27
includes taxes & fees
7.8/10 Good! (1,004 reviews)
The rooms were specious and clean
Reviewed on Apr 19, 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.
