Kingston Vacation Packages
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Top Kingston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $831, price is now CA $645 per person
CA $645
per person
Apr 24 - Apr 27
found 23 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Staff was great. The hotel is quirky and cool with an unbeatable location right in the middle of shopping, theater and restaurants. Easily walkable to the Art Institute and Millennium Park. The rooms are not large, and could use some new furniture, but very clean.
Will definitely be back.
Reviewed on Feb 14, 2026
Holiday Inn Chicago North-Evanston by IHG
Downtown Evanston
Price was CA $1,010, price is now CA $769 per person
CA $769
per person
Apr 24 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,652 reviews)
Comfortable bed, clean room, nice hotel
Reviewed on Feb 12, 2026
The Wade
Downtown Chicago
Price was CA $992, price is now CA $757 per person
CA $757
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
I had a great stay at the Wade Hotel in Chicago! The room was very clean and comfortable, and the staff was friendly, professional, and welcoming from check-in to check-out. The amenities were convenient, and the location made it easy to get around the city. I would definitely stay here again and recommend it to anyone visiting Chicago.
Reviewed on Feb 9, 2026
Kingston Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Feb 26 to Feb 27
CA $87
CA $99 total
Feb 26 - Feb 27
includes taxes & fees
9/10 Wonderful! (1,503 reviews)
BEAUTIFUL
Reviewed on Feb 10, 2026
Holiday Inn Rockford by IHG
7550 E State Street Rockford IL
Fully refundable
The price is CA $127 per night from Mar 17 to Mar 18
CA $127
CA $144 total
Mar 17 - Mar 18
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Clean, friendly staff.
Reviewed on Feb 7, 2026
Hilton Garden Inn Rockford
7675 Walton St Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Feb 26 to Feb 27
CA $157
CA $179 total
Feb 26 - Feb 27
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Very friendly. Great stay!
Reviewed on Feb 11, 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.
