Kingston Vacation Packages

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Top Kingston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,315, price is now CA $788 per person
CA $788
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on Aug. 25, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,838, price is now CA $1,118 per person
CA $1,118
per person
Nov 21 - Nov 24
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,928, price is now CA $1,182 per person
CA $1,182
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was CA $1,699, price is now CA $1,070 per person
CA $1,070
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
We loved the experience! We shall come back again😊

Reviewed on Aug. 24, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was CA $2,075, price is now CA $1,322 per person
CA $1,322
per person
Nov 3 - Nov 6
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
10/10 Exceptional! (2 reviews)

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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 $100 per night from Sep 2 to Sep 3
CA $100
CA $114 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (1,285 reviews)
"Good service."

Reviewed on Aug. 25, 2025

Baymont by Wyndham Rockford
Econo Lodge

Econo Lodge

2 out of 5
7712 Potawatomi Trail, Rockford, IL
Fully refundableReserve now, pay when you stay
The price is CA $86 per night from Aug 27 to Aug 28
CA $86
CA $98 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very Good! (943 reviews)
"It was a decent room. Clean bed but I swear something bite me at least a dozen times while I was sleeping last night. Also the water drainage in the shower needs to be checked."

Reviewed on Aug. 25, 2025

Econo Lodge
Country Inn & Suites by Radisson, Sycamore, IL

Country Inn & Suites by Radisson, Sycamore, IL

2.5 out of 5
1450 South Peace Road, Sycamore, IL
Fully refundable
The price is CA $129 per night from Aug 31 to Sep 1
CA $129
CA $143 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (871 reviews)
"Expedia I was disappointed that you did not let Radison know I had asked two times for a room for a disabled person. They were unaware that I had requested a disabled room."

Reviewed on Aug. 19, 2025

Country Inn & Suites by Radisson, Sycamore, IL
See all 131 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Kingston vacation package cost?
Offering great value package deals from CA $788 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.