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Lowest round trip fares by airline from Chicago and Kingston

Cheapest prices ($116 One Way, $323 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Kingston

The Jamaica Pegasus Hotel

The Jamaica Pegasus Hotel

3.5 out of 5
81 Knutsford Boulevard, Kingston
The price is $204 per night from Apr 20 to Apr 21
$204
per night
Apr 20 - Apr 21
Stay at this 3.5-star spa hotel in Kingston. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff in our ...
8/10 Very Good! (611 reviews)
"Everything was well put together"

Reviewed on Apr 18, 2024

The Jamaica Pegasus Hotel
Eden Gardens Wellness Resort & Spa

Eden Gardens Wellness Resort & Spa

3.5 out of 5
39 Lady Musgrave Road, New Kingston, Kingston, Saint Andrew
Stay at this 3.5-star spa resort in Kingston. Enjoy free breakfast, free WiFi, and 2 restaurants. Popular attractions Bob Marley Museum and Independence Park ...
7.4/10 Good! (481 reviews)
"I love that there are restaurants on the property. It was very nice staying here. I felt safe with the security and the staff was very nice."

Reviewed on Mar 12, 2020

Eden Gardens Wellness Resort & Spa
Spanish Court Hotel - A Small Luxury Hotel

Spanish Court Hotel - A Small Luxury Hotel

4.5 out of 5
1 St Lucia Avenue, Kingston, Saint Andrew
The price is $170 per night from May 10 to May 11
$170
per night
May 10 - May 11
Stay at this 4.5-star luxury hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9.4/10 Exceptional! (1,059 reviews)
"Would definitely stay again!"

Reviewed on Apr 15, 2024

Spanish Court Hotel - A Small Luxury Hotel
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.

Fly From Chicago to Kingston

Origin
Chicago
Destination
Kingston
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Cheap flights from Chicago to Kingston

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

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Save Even More Time and Money With a Kingston Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Kingston vacation that you can't get when you book flights and hotel separately.

Relax in Kingston With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.