CHI - KIN

$145 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 3/24. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$445
Overall average: $537
Spirit Airlines
Tue 3/24Thu 3/26
ORD - KIN • 1 stop
Cheapest one-way
$145
Typical prices: $183-$352
Spirit Airlines
Tue 3/24
ORD - KIN • 1 stop
Top airlines
Cheapest • from $445 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Kingston. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $431 (round-trip)
Shortest trip • 6h 14m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 27% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
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, Mar 24 - Thu, Mar 26
Spirit Airlines Logo
5:05 am - 11:35 am
ORD
-
KIN
6h 30m
1 stop
Spirit Airlines Logo
12:32 pm - 7:51 pm
KIN
-
ORD
7h 19m
1 stop
$445Spirit Airlines
Tue, Mar 17 - Tue, Mar 24
Spirit Airlines Logo
5:05 am - 11:35 am
ORD
-
KIN
6h 30m
1 stop
Spirit Airlines Logo
12:32 pm - 7:51 pm
KIN
-
ORD
7h 19m
1 stop
$454Spirit Airlines
Tue, Mar 17 - Wed, Mar 25
Spirit Airlines Logo
5:05 am - 11:35 am
ORD
-
KIN
6h 30m
1 stop
Spirit Airlines Logo
12:32 pm - 7:51 pm
KIN
-
ORD
7h 19m
1 stop
$457Spirit Airlines
Sun, Apr 5 - Wed, Apr 8
Spirit Airlines Logo
5:05 am - 11:35 am
ORD
-
KIN
6h 30m
1 stop
Spirit Airlines Logo
12:32 pm - 7:51 pm
KIN
-
ORD
7h 19m
1 stop
$464Spirit Airlines
Mon, Apr 13 - Mon, Apr 27
Spirit Airlines Logo
7:17 am - 11:35 am
ORD
-
KIN
28h 18m
1 stop
Spirit Airlines Logo
3:18 pm - 9:36 am
KIN
-
ORD
18h 18m
1 stop
$471Spirit Airlines
Wed, Mar 18 - Tue, Mar 24
Multiple Airlines Logo
6:36 pm - 11:35 am
ORD
-
KIN
16h 59m
1 stop
Multiple Airlines Logo
12:32 pm - 8:23 am
KIN
-
ORD
19h 51m
2 stops
$483Multiple Airlines
Sun, Apr 19 - Sun, Apr 26
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
14h 00m
1 stop
Delta Logo
9:00 am - 4:26 pm
KIN
-
MDW
7h 26m
1 stop
$516Delta
Tue, Sep 1 - Mon, Sep 7
Delta Logo
1:05 pm - 8:04 pm
MDW
-
KIN
6h 59m
1 stop
Delta Logo
9:00 am - 9:46 pm
KIN
-
MDW
12h 46m
1 stop
$536Delta
Wed, Sep 2 - Sun, Sep 6
Delta Logo
1:05 pm - 8:04 pm
MDW
-
KIN
6h 59m
1 stop
Delta Logo
9:00 am - 8:42 am
KIN
-
MDW
23h 42m
2 stops
$541Delta
Mon, Apr 20 - Sat, Apr 25
Delta Logo
12:52 pm - 8:00 pm
MDW
-
KIN
7h 08m
1 stop
Delta Logo
9:00 am - 10:28 pm
KIN
-
MDW
13h 28m
1 stop
$586Delta
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.

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 April, where tickets cost $440 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $1,007 and $982 respectively.

Good to know

Low seasonNovember
Cheapest flight$145
Best time to beat the crowds but there is an average 66% increase in price.
Most popular time to fly and prices are also 12% lower on average.
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 $145 for a one-way ticket and $445 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 $537 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 $596 and an overall rating of 7.1.

  • 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 8278 reviews
7.8Entertainment
7.9Comfort
8.5Crew
8.1Boarding
7.2Food
Airline reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

8.0 ExcellentMary, Mar 2026
LGA - MKE
Read more Delta reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

My flight was delayed by over an hour and the turbulance was horrible.

Everything is an additional fee. No one said anything when I checking in and got my boarding pass about my small carry on suitcase. Charged me $100 at the gate for that little bag that I still had to take with me. Delays for both flights for no reason and then when I asked everyone said something different. Never flying spirit again. If it was just one thing maybe. This was a show from the minute I got to the airport.

I had a great experience from booking to boarding to landing. This was the best experience from all the flights I’ve had with Spirit so far! The price and times were affordable and perfect. I will fly with them again soon!

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

First off, I had a conversation with a flight attendant that was working this flight. I overheard her telling another flight attendant while we were in line for Chic-Fil-A that the flight was not going to land until 12:47 pm. I found this odd since the flight was to take off at 1:03. I commented to the flight attendant that was going to mess up the on-time take-off She said. if you fly alot you will notice that it's a good thing if the flight even arrives at all. I said that was a low bar. I think that flight attendants represent their airlines whether on board or in the airport ordering food. I was surprised to hear such negativity. However, I have noticed that Spirit flight attendants are usually in a sour mood.. Eventually the flight arrived and I boarded and the flight took off an hour late. There was no direction about the on-board wi-fi. Nor was there any info in the seat back pocket. I don't know if there was wi-fi or not, There were no complimentary snacks or drinks for my row 36 as there was turbulence and the captain asked the flight attendants to stop serving just as they were close to my row. When the turbulence stopped, they did have time to serve us but they did not. Upon arriving, the flight attendant asked anyone not having to catch a flight to Ft. Laudersle which was a tight connection to sit down and let those people pass. I complied but I could not help thinking that if Spirit would have took off on time that they would not have to inconvenience their passengers. All in all, I think Spirit is a mediocre airline at best. There are so many things they could do to improve. Yet, since I only fly Spirit infrequently preferring Southwest and Delta, I like to see if they are improving and sadly no, they are not. One good thing - nice modern seats and interiors.

I have to wait for the flight for 3 hours. The gate was switching for 5 times. Made feel frustrated. Delays took all my sleep. I went to work without any sleep.

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

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

Information on your arrival and departure airports