Kingston Vacation Packages
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Top Kingston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,118, price is now CA $768 per person
CA $768
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,871, price is now CA $1,241 per person
CA $1,241
per person
May 24 - May 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The room was clean, spacious, with good views.
Reviewed on Apr 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,895, price is now CA $1,259 per person
CA $1,259
per person
Jun 18 - Jun 21
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included
Reviewed on Apr 12, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,419, price is now CA $1,018 per person
CA $1,018
per person
May 24 - May 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
I would highly recommend this hotel. The only issue we had was that there was not daily cleaning. I actually never saw hotel cleaning staff in the halls, but the room and hotel were very clean so I am not sure where they were. The hotel is near so many attractions and restaurants. On the second floor is a room with a pool table, air hockey, and other games which was a nice break.
Reviewed on Apr 13, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,075, price is now CA $1,522 per person
CA $1,522
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 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 Apr 15 to Apr 16
CA $87
CA $99 total
Apr 15 - Apr 16
includes taxes & fees
9/10 Wonderful! (1,586 reviews)
Small breakfast thought it would have some eggs
Reviewed on Apr 13, 2026
Holiday Inn Rockford by IHG
7550 E State Street Rockford IL
Fully refundable
The price is CA $163 per night from Apr 28 to Apr 29
CA $163
CA $185 total
Apr 28 - Apr 29
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
When booking this room I had specifically asked if there was a hot tub and they had said yes but there is not one. Also had asked if they do rides to the casino also said yes but they don’t. Waited in line for a long time on checking into hotel, need more then one person during “peak hours” otherwise ...
Reviewed on Mar 27, 2026
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from May 13 to May 14
CA $170
CA $193 total
May 13 - May 14
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
Always a great stay
Reviewed on Apr 5, 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.
