Kingston Vacation Packages
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Top Kingston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,667, price is now CA $1,255 per person
CA $1,255
per person
Apr 28 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special!
Reviewed on Mar 16, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,263, price is now CA $1,452 per person
CA $1,452
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was in a perfect spot for us to visit Chicago and have a comfortable place to stay
Reviewed on Mar 21, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,331, price is now CA $1,504 per person
CA $1,504
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great location, views, & amenities.
Reviewed on Mar 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,717, price is now CA $1,289 per person
CA $1,289
per person
Jun 5 - Jun 8
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
Hilton Garden Inn Chicago Central Loop
Downtown Chicago
Price was CA $1,928, price is now CA $1,458 per person
CA $1,458
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,300 reviews)
It was a good place to spend a staycation weekend. Well located and friendly staff
Reviewed on Mar 16, 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 $103 per night from Apr 12 to Apr 13
CA $103
CA $117 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (1,549 reviews)
Room was clean, staff were friendly, breakfast was typical fare. An okay place to stay when traveling thru Rockford.
Reviewed on Mar 20, 2026
Holiday Inn Rockford by IHG
7550 E State Street Rockford IL
Fully refundable
The price is CA $154 per night from Apr 5 to Apr 6
CA $154
CA $175 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
I stay 2-3 nights every week for work I have stayed at a lot of the hotels in that area Great food at scoreboard bar and grill Great staff at the hotel
Reviewed on Mar 19, 2026
Hilton Garden Inn Rockford
7675 Walton St Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Mar 29 to Mar 30
CA $147
CA $168 total
Mar 29 - Mar 30
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Pool was cold.
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.
