CHI - KIN

$157 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 5/11. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$409
Overall average: $573
Spirit Airlines
Mon 4/13Mon 4/27
ORD - KIN • 1 stop
Cheapest one-way
$157
Typical prices: $240-$258
Spirit Airlines
Mon 5/11
ORD - KIN • 1 stop
Top airlines
Cheapest • from $409 (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

Mon, Apr 13 - Mon, Apr 27
Spirit Airlines Logo
4:36 pm - 11:35 am
ORD
-
KIN
18h 59m
1 stop
Spirit Airlines Logo
3:18 pm - 9:36 am
KIN
-
ORD
18h 18m
1 stop
$409Spirit Airlines
Mon, Apr 13 - Mon, Apr 27
Spirit Airlines Logo
11:25 am - 11:35 am
ORD
-
KIN
24h 10m
2 stops
Spirit Airlines Logo
3:18 pm - 9:36 am
KIN
-
ORD
18h 18m
1 stop
$426Spirit Airlines
Mon, Apr 13 - Mon, Apr 27
Spirit Airlines Logo
11:25 am - 11:35 am
ORD
-
KIN
24h 10m
2 stops
Spirit Airlines Logo
3:18 pm - 10:23 am
KIN
-
ORD
19h 05m
2 stops
$451Spirit Airlines
Mon, Apr 27 - Mon, May 4
Multiple Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
Multiple Airlines Logo
3:18 pm - 7:55 am
KIN
-
ORD
40h 37m
2 stops
$461Multiple Airlines
Mon, Apr 27 - Mon, May 4
Spirit Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
Spirit Airlines Logo
3:18 pm - 9:31 am
KIN
-
ORD
18h 13m
1 stop
$476Spirit Airlines
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
8:45 am - 1:55 pm
ORD
-
KIN
29h 10m
2 stops
Multiple Airlines Logo
3:18 pm - 12:27 am
KIN
-
ORD
9h 09m
1 stop
$480Multiple Airlines
Wed, Apr 15 - Mon, Apr 20
Multiple Airlines Logo
1:55 pm - 12:35 pm
ORD
-
KIN
22h 40m
2 stops
Multiple Airlines Logo
3:18 pm - 12:24 am
KIN
-
ORD
9h 06m
1 stop
$483Multiple Airlines
Sun, Sep 6 - Thu, Sep 10
Delta Logo
6:00 am - 8:04 pm
MDW
-
KIN
14h 04m
1 stop
Delta Logo
9:00 am - 3:27 pm
KIN
-
MDW
6h 27m
1 stop
$606Delta
Thu, Jun 11 - Wed, Jun 17
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
14h 00m
1 stop
Delta Logo
9:00 am - 6:31 pm
KIN
-
MDW
9h 31m
2 stops
$611Delta
Thu, May 14 - Thu, May 21
Delta Logo
10:59 am - 8:00 pm
MDW
-
KIN
9h 01m
1 stop
Delta Logo
9:00 am - 9:09 pm
KIN
-
MDW
12h 09m
1 stop
$626Delta
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$157
Best time to beat the crowds but there is an average 66% increase in price.
Most popular time to fly and prices are also 13% 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 $157 for a one-way ticket and $409 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?

    oneworld is the only airline alliance operating flights between Chicago and Kingston.

  • 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 $613 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 8292 reviews
7.2Food
7.9Comfort
8.5Crew
8.1Boarding
7.8Entertainment
Airline reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

10.0 ExcellentAnonymous, Mar 2026
ATL - DTW
Read more Delta reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

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.

The gate got changed several times and the flight was delayed over an hour. Awful experience

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.

Not enough crew members so we had to wait for more to arrive and they could never give us updates timing. Not even water for free on board. Bare bones airplane- there wasn’t even a seat back pocket to put things into. Spirit is cheap for a reason but this was dismal

The plane was clean and crew was nice. Can’t speak on food as I did not have any

Flight was delayed, then undelayed, then delayed again. Gate was changed to the other side of the airport. Horrible seats with no screens. Spirit os truly awful, even for a budget option.

flight delayed because of poor staffing and organization - confusion from gate agents and flight attendant supervisors scheduling a missing flight attendant. flight delay 1 hr 30 min

I liked the quickness of the boarding process. Things were run smoothly and the staff was very professional. The overall experience was great.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

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

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.

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

Information on your arrival and departure airports