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 8/2. 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

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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Flights 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, Aug 19 - Mon, Aug 25
Spirit Airlines Logo
6:50 pm - 11:27 amORD-KIN
16h 37m1 stop
Spirit Airlines Logo
9:33 am - 11:59 pmKIN-ORD
14h 26m1 stop
$335Spirit Airlines
Find Deal
Fri, Aug 8 - Thu, Aug 21
Spirit Airlines Logo
5:40 pm - 7:47 amORD-KIN
14h 07m1 stop
Spirit Airlines Logo
9:33 am - 5:45 pmKIN-ORD
8h 12m1 stop
$342Spirit Airlines
Find Deal
Sun, Oct 26 - Wed, Nov 5
Delta Logo
6:00 am - 8:00 pmORD-KIN
14h 00m1 stop
Delta Logo
9:00 am - 6:56 pmKIN-ORD
10h 56m1 stop
$383Delta
Find Deal
Mon, Oct 27 - Fri, Nov 7
Delta Logo
10:35 am - 8:00 pmORD-KIN
9h 25m2 stops
Delta Logo
9:00 am - 6:56 pmKIN-ORD
10h 56m1 stop
$388Delta
Find Deal
Tue, Aug 12 - Sat, Aug 23
 Logo
10:00 am - 11:27 amORD-KIN
25h 27m3 stops
 Logo
6:25 pm - 9:52 amKIN-ORD
15h 27m2 stops
Wed, Aug 6 - Thu, Aug 14
 Logo
1:07 am - 1:53 pmORD-KIN
12h 46m1 stop
 Logo
9:33 am - 11:59 pmKIN-ORD
14h 26m1 stop
Thu, Aug 7 - Wed, Aug 13
JetBlue Logo
6:15 am - 6:09 pmORD-KIN
11h 54m1 stop
JetBlue Logo
1:06 am - 10:47 amKIN-ORD
9h 41m1 stop
$501JetBlue
Find Deal
Sun, Nov 16 - Sat, Nov 22
American Airlines Logo
8:10 am - 9:30 pmORD-KIN
12h 20m1 stop
American Airlines Logo
8:30 am - 4:05 pmKIN-ORD
8h 35m1 stop
$532American Airlines
Find Deal
Sun, Nov 16 - Thu, Dec 4
American Airlines Logo
7:00 am - 1:55 pmORD-KIN
5h 55m1 stop
American Airlines Logo
6:20 am - 4:15 pmKIN-ORD
10h 55m2 stops
$537American Airlines
Find Deal
Tue, Sep 16 - Thu, Sep 25
JetBlue Logo
6:45 am - 7:06 pmORD-KIN
12h 21m1 stop
JetBlue Logo
2:10 am - 12:10 pmKIN-ORD
10h 00m1 stop
$539JetBlue
Find Deal
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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.

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 March, where the average cost of round-trip tickets is $1,041 and $761 respectively.

Good to know

Low seasonJuly
High seasonMarch
Cheapest flight$151
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly with an average 31% 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 $335 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, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Kingston, with Star Alliance 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 $638 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $596 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.
8.0
DeltaOverall score based on 7967 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

10.0 ExcellentDena, Jun 2025ONT - ATL
Read more Delta reviews

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

The crew was very nice. I would like to see them offer basic refreshments just like a soda and pretzels, etc. for free.

Unprepared for the very expensive carry-on cost. Still was our best option since it was a direct flight and the best times.

Onboarding was an easy process. Staff waa friendly and courteous. Should have a complimentary snack and drink. We paid $900 round trip for two to myrtle from New York, which is an expensive fare. Going to the seats were not in good shape but our return home, the air plane seemed to be new with comfortable seating with slightly more space. If traveling again, we will still consider flying SpIrit.

I missed my flight because I was not informed that I had to check in 45 minutes before my flight and I was not allowed to check in any time after that. I was there at boarding time and their customer service was poor and they told me since I didn't check in 45 minutes prior, I couldn't get my boarding pass. I received an email containing my "e ticket" which I Thought was going to get me boarded.But but they said that was just an Itinerary and it was no good to help me get on the plane. I had already missed one flight earlier that afternoon and had to pay for this flight.And then when I missed it they told me it was gonna cost me another $99 to reschedule my flight

Great experience overall. Early boarding, no delays. Drinks and snacks are not included in price and very expensive. Seats are not very comfortable. Not as much space or padding as other airlines. Good for a quick cheap flight.

My flight got cancelled by Spirit airlines, it was bad experience to me

Crew from Columbus to Atlanta excellent. Flight overall was good. Flight crew from Atlanta to Newark were average probably because they had to deal with overbooked flight and obnoxious people on the flight. Ground crew in terminal needed to do a better job limiting luggage boarding the plane.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

It was absolutely awesome. The crew was welcoming to all, not just the first class. They were full of energy. The in-cabin music was an excellent choice, not boring like most airlines. We were ready for takeoff ahead of time. Pilots were great. Smooth takeoff and landing. The plane was beautiful and nicely cleaned. This was truly a fantastic flight. I fly Delta and American all the time. I was apprehensive about Spirit. I will definitely be looking for Spirit first. Thanks for a great experience.

Didn't like size of seats. Found charges for checked luggage and carry on too high

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

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