
Hillsdale Vacation Packages
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Top Hillsdale Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,554, price is now CA $1,181 per person
CA $1,181
per person
May 16 - May 19
found 9 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,919, price is now CA $1,272 per person
CA $1,272
per person
Jun 5 - Jun 8
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
We only stayed for 1 night but the room was exceptionally clean, smelled fresh, and we had an amazing view! Would highly recommend
Reviewed on Mar 22, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,973, price is now CA $1,312 per person
CA $1,312
per person
May 16 - May 19
found 9 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with a fantastic shower and amazing shampoo, conditioner and lotion! I’ve even looked into buying it for my home. The breakfast buffet was unbelievable! The food was plentiful with more options than I thought possible. Even more impressive was the breakfast staff who kept the tables clean and the food available, hot and fresh. The hosts took a special interest in knowing the guests, and I know this first hand. My birthday fell during our stay, and the breakfast staff had a table waiting for my family and presented a birthday brownie with the words “Happy Birthday” written in chocolate sauce! Unfortunately, I had unexpectedly been hospitalized for emergency surgery so I missed the opportunity to experience their grand gesture, but the first morning I walked into breakfast after being discharged from the hospital, the host having never see me, asked if my family had given me the brownie. l was blown away! Will I stay again? Without any hesitation!!! Excellent choice!!
Reviewed on Mar 22, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,116, price is now CA $1,572 per person
CA $1,572
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.
Reviewed on Mar 14, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,701, price is now CA $1,284 per person
CA $1,284
per person
Jun 5 - Jun 8
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
Hillsdale Hotel Deals

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 29 to Mar 30
CA $123
CA $137 total
Mar 29 - Mar 30
includes taxes & fees
7.6/10 Good! (1,005 reviews)
Great place to stay in downtown Davenport!
Reviewed on Mar 22, 2026

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 2 to Apr 3
CA $125
CA $141 total
Apr 2 - Apr 3
includes taxes & fees
9/10 Wonderful! (1,237 reviews)
Excellent location for the vibrant areana. Friendly, clean, and will be back.
Reviewed on Mar 22, 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! (924 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.
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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.







