Hillsdale Vacation Packages
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Top Hillsdale Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,447, price is now CA $948 per person
CA $948
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that
Reviewed on Jun 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,070, price is now CA $1,456 per person
CA $1,456
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
This is our second time staying at the sable and it was wonderful! The staff is amazing and friendly! The elevators were out and we got lost a couple times getting to our room, and every single staff member that we would run into each time was so helpful and kind in finding where we were supposed to go! One of the housekeepers even stopped what she was doing to walk us to our correct floor when she realized we were lost! She was so incredibly nice! The views are incredible, the location is incredible, and the staff is incredible! Will definitely be coming back on our next trip to Chicago/Navy Pier!
Reviewed on Jun 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,941, price is now CA $1,396 per person
CA $1,396
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.
Reviewed on Jun 12, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,346, price is now CA $981 per person
CA $981
per person
Aug 13 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 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 $92 per night from Jun 25 to Jun 26
CA $92
CA $103 total
Jun 25 - Jun 26
includes taxes & fees
7.2/10 Good! (1,016 reviews)
"It was a nice place but there was no toilet paper in the room and the blankets smelled like bleach. The beds were comfortable and slept well. The tv remote barely worked. Needed to be replaced. Normally it’s a nice place to stay but they need to do a better job at making sure everything works and ..."
Reviewed on Jun 13, 2026
Isle Casino Hotel - Bettendorf
1777 Isle Pkwy Bettendorf IA
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jun 21 to Jun 22
CA $112
CA $146 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
"N/A"
Reviewed on Jun 10, 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 Jun 21 to Jun 22
CA $136
CA $153 total
Jun 21 - Jun 22
includes taxes & fees
7.8/10 Good! (1,027 reviews)
"This is a very nice hotel. I though the breakfast should have been included."
Reviewed on Jun 13, 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.
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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.
