Kingston Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Kingston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,030, price is now CA $741 per person
CA $741
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,010 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,790, price is now CA $1,272 per person
CA $1,272
per person
Sep 5 - Sep 8
found 16 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Big rooms, nice lobby, and great breakfast. Good location and easy check in.

Reviewed on Jul 20, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,178, price is now CA $854 per person
CA $854
per person
Sep 5 - Sep 8
found 16 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The hotel location is excellent, the room was per expectations, and the staff were super helpful and friendly.

Reviewed on Jul 20, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,027, price is now CA $755 per person
CA $755
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,484 reviews)
Good and easy service

Reviewed on Jul 20, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,737, price is now CA $1,296 per person
CA $1,296
per person
Sep 5 - Sep 8
found 16 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)
The Navy Pier where this out standing property is a wonderful location in a wonderful city. The view is fantastic and the room perfect. The amenities around could not be better. Highly suggested on our side

Reviewed on Jul 20, 2026

Ready to book your vacation to Kingston?

 

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Kingston Hotel Deals

Baymont by Wyndham Rockford

Baymont by Wyndham Rockford

3 out of 5
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Jul 27 to Jul 28
CA $113
CA $129 total
Jul 27 - Jul 28
includes taxes & fees
Baymont by Wyndham Rockford
Econo Lodge Rockford Casino Area

Econo Lodge Rockford Casino Area

2 out of 5
7712 Potawatomi Trail Rockford IL
Fully refundable
The price is CA $87 per night from Jul 27 to Jul 28
CA $87
CA $99 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,097 reviews)
"This hotel was not bad but not exceptional. The staff was really friendly and welcoming. We check in early without fee.The beds were small and the room smelled of a mixture of dampness and cigarette smoke. The shower is small and hot water was not quickly available. Overall if you are looking for ..."

Reviewed on Jul 19, 2026

Econo Lodge Rockford Casino Area
La Quinta Inn & Suites by Wyndham Rockford

La Quinta Inn & Suites by Wyndham Rockford

3 out of 5
7401 Walton St Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jul 27 to Jul 28
CA $112
CA $128 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Just make sure they honor what you paid for, since sometimes they claim an update was made and your plan got changed because there were no notes on file."

Reviewed on Jul 19, 2026

La Quinta Inn & Suites by Wyndham Rockford
See all 136 properties in Kingston
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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Frequently asked questions

How much does a Kingston vacation package cost?
Offering great value package deals from CA $741 on Expedia, you'll be pleasantly surprised at how much a vacation to Kingston costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Kingston?
If you're hoping to score a cheap Kingston vacation package, consider planning a trip in January, February and April. You're likely to find better rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Kingston?
The ideal length for your Kingston vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to check out all the leading attractions and discover some hidden treasures along the way.
How to find the best Kingston package deals?
Start your search for a Kingston package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Kingston package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Kingston escape underway.
Is it cheaper to book a Kingston vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can customize your Kingston escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Kingston?
If you're considering a spur-of-the-moment Kingston adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Kingston?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to vacation in Kingston.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to flights and experiences. Your hotel will likely be the largest expense during your trip to Kingston.
  3. Work out your trip length: Think about how long you'd like to spend discovering Kingston. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the ideal Kingston vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.