CHI - KIN

$151 Find Cheap Flights from Chicago to Kingston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kingston departing on 11/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Kingston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kingston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kingston, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Chicago to Kingston (CHI-KIN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kingston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Kingston

Tue, Dec 2 - Tue, Dec 9
Spirit Airlines Logo
5:00 am - 1:21 pmORD-KIN
7h 21m1 stop
Spirit Airlines Logo
1:19 pm - 8:01 pmKIN-ORD
7h 42m1 stop
$346Spirit Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Spirit Airlines Logo
3:43 pm - 12:14 pmORD-KIN
19h 31m1 stop
Spirit Airlines Logo
1:19 pm - 8:01 pmKIN-ORD
7h 42m1 stop
$353Spirit Airlines
Find Deal
Sun, Dec 7 - Sat, Dec 13
Multiple Airlines Logo
3:20 pm - 12:14 pmORD-KIN
19h 54m1 stop
Multiple Airlines Logo
1:19 pm - 8:01 pmKIN-ORD
7h 42m1 stop
$357Multiple Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Multiple Airlines Logo
4:22 pm - 12:14 pmORD-KIN
42h 52m2 stops
Multiple Airlines Logo
1:19 pm - 8:01 pmKIN-ORD
7h 42m1 stop
$378Multiple Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11
American Airlines Logo
2:40 pm - 10:34 pmORD-KIN
6h 54m1 stop
American Airlines Logo
7:00 am - 6:07 pmKIN-ORD
12h 07m1 stop
$434American Airlines
Find Deal
Tue, Nov 25 - Tue, Dec 2
American Airlines Logo
8:10 am - 10:13 pmORD-KIN
13h 03m1 stop
American Airlines Logo
7:30 am - 3:56 pmKIN-ORD
9h 26m2 stops
$438American Airlines
Find Deal
Sat, Jan 31 - Sat, Feb 7
Delta Logo
6:00 am - 8:00 pmMDW-KIN
13h 00m1 stop
Delta Logo
9:00 am - 3:40 pmKIN-MDW
7h 40m1 stop
$445Delta
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Mon, Feb 16 - Fri, Feb 20
Delta Logo
9:48 am - 8:00 pmORD-KIN
9h 12m1 stop
Delta Logo
9:00 am - 11:49 pmKIN-ORD
15h 49m1 stop
$445Delta
Find Deal
Thu, Dec 4 - Tue, Dec 9
WestJet Logo
9:59 am - 3:33 pmMDW-KIN
28h 34m2 stops
WestJet Logo
4:30 pm - 6:18 pmKIN-MDW
26h 48m2 stops
$815WestJet
Find Deal
Thu, Dec 4 - Wed, Dec 10
WestJet Logo
9:59 am - 3:33 pmMDW-KIN
28h 34m2 stops
WestJet Logo
4:30 pm - 1:10 pmKIN-MDW
21h 40m2 stops
$912WestJet
Find Deal

Everything you should know

Top airlines
Spirit Airlines
Cheapest • from $346 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 29% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$346
Overall average: $883
Spirit Airlines
Tue 12/2Tue 12/9
ORD - KIN • 1 stop
Cheapest one-way
$151
Typical prices: $175-$260
Spirit Airlines
Wed 11/19
ORD - KIN • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Kingston!
Booking Insights

KAYAK's insights & trends for Chicago to Kingston flights

Get data-powered insights and trends into flights from Chicago to Kingston to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Kingston?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Kingston departing in December.

What’s the cheapest day of the week to fly from Chicago to Kingston?

The average price of all round-trip flights from Chicago to Kingston clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Kingston, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Kingston, Saturday is the cheapest day to fly and Tuesday is the most expensive.

What is the cheapest month to fly from Chicago to Kingston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Kingston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Kingston is February, where tickets cost $380 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $781 and $614 respectively.

Good to know

Low seasonJuly
Cheapest flight$151
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to Kingston

When to book flights from Chicago to Kingston

Are your dates flexible? Find out the best times to travel from Chicago to Kingston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Kingston

  • What is the cheapest flight from Chicago to Kingston?

    In the last 3 days, the lowest price for a flight from Chicago to Kingston was $151 for a one-way ticket and $346 for a round-trip.

  • Do I need a passport to fly between Chicago and Kingston?

    A passport is required to fly from Chicago to Kingston.

  • Which airports will I be using when flying from Chicago to Kingston?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Kingston Norman Manley is the only airport in Kingston. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which aircraft models fly most regularly from Chicago to Kingston?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Kingston?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Kingston, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Kingston, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Kingston are Delta and American Airlines. With an average price for the route of $572 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $563 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Kingston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Kingston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Kingston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kingston from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Kingston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kingston with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Kingston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kingston from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Chicago to Kingston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kingston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Kingston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8004 reviews
8.2Boarding
7.9Entertainment
8.5Crew
7.9Comfort
7.3Food
Airline reviews

I truly love flying with Delta. They have always treated me with the upmost respect

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

The Hawaiian lady that boarded me was rude and the one help me a the ticket counter was rude

My experience was terrible. They cancelled my flight twice. They kept delaying it and leading me on, acting like the flight was going to go when it never had a chance. I missed out on valuable family time because of spirit and I won’t be flying with them again.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

The flight was cancelled at the last minute. Will never fly Spirit again. Without a doubt the worst airline around.

My flight was delayed several times and eventually cancelled. Then the re-booked flight for 8pm was delayed multiple times over, and eventually it would have forced me to be at the airport for 9 hours. I accepted a rebook for the following day, fortunately I was able to stay with my friend again in New York, but if I didn’t have him as a resource it would have been much more upsetting.

Horrible, delay after delay due to our plane needing fuel.

Rough landings but comfortable and affordable if you can pack light

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

Everything you need to know for your flight from Chicago to Kingston

Information on your arrival and departure airports

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