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CHI - KIN

$165 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 6/6. 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
0 bags
Thu 6/13
Thu 6/20

Search 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
In the last 7 days travelers have searched 42,566,405 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Chicago to Kingston (CHI-KIN)

 
These are the cheapest deals for flights from Chicago to Kingston currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Kingston

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Kingston.

Recent one-way flight deals from Chicago to Kingston

Only flying one-way? Below are some of the best one-way flight deals from Chicago to Kingston found on KAYAK recently.

Recent last minute flight deals from Chicago to Kingston

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to Kingston.

Recent direct flight deals from Chicago to Kingston

The latest deals for direct flights from Chicago to Kingston so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to Kingston

Find recent round-trip train or bus tickets from Chicago to Kingston.

All round-trip flight deals to Kingston

The cheapest plane tickets to Kingston found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:40 pm - 11:25 amORD-KIN
16h 45m1 stop
12:26 pm - 12:55 amKIN-ORD
12h 29m1 stop
$341Spirit Airlines
Find Deal
Mon, Jun 3 - Thu, Jun 6
6:40 pm - 11:18 amORD-KIN
16h 38m1 stop
12:26 pm - 12:55 amKIN-ORD
12h 29m1 stop
$354Spirit Airlines
Find Deal
Tue, Jun 25 - Fri, Jul 5
6:00 am - 7:56 pmMDW-KIN
13h 56m1 stop
9:10 am - 5:59 pmKIN-MDW
8h 49m1 stop
$468Delta
Find Deal
Thu, Jun 6 - Sun, Jun 16
7:12 pm - 7:56 pmORD-KIN
24h 44m2 stops
9:10 am - 9:21 amKIN-ORD
24h 11m2 stops
$479Delta
Find Deal
Mon, Jun 3 - Fri, Jun 7
9:55 am - 6:21 pmORD-KIN
8h 26m2 stops
6:00 am - 5:40 pmKIN-ORD
11h 40m2 stops
$483American Airlines
Find Deal
Wed, Oct 23 - Wed, Oct 30
6:40 pm - 11:18 amORD-KIN
16h 38m1 stop
7:00 pm - 4:28 pmKIN-ORD
21h 28m2 stops
Tue, Jun 4 - Fri, Jun 7
2:35 pm - 11:18 amMDW-KIN
20h 43m2 stops
7:00 pm - 4:17 pmKIN-MDW
21h 17m1 stop
Mon, Jun 10 - Mon, Jun 17
8:21 am - 11:25 pmORD-KIN
15h 04m2 stops
7:00 am - 4:04 pmKIN-ORD
10h 04m2 stops
$592American Airlines
Find Deal
Fri, Nov 1 - Tue, Nov 5
9:05 am - 6:04 pmORD-KIN
8h 59m1 stop
2:59 am - 5:26 pmKIN-ORD
14h 27m1 stop
$627JetBlue
Find Deal
Wed, Oct 23 - Tue, Oct 29
10:35 am - 6:28 pmORD-KIN
7h 53m1 stop
7:48 pm - 9:50 amKIN-ORD
14h 02m1 stop
$863JetBlue
Find Deal
Mon, Jun 24 - Sat, Jun 29
6:40 pm - 11:18 amORD-KIN
16h 38m1 stop
$165Spirit Airlines
Find Deal
Thu, Jun 6
6:40 pm - 11:18 amORD-KIN
16h 38m1 stop
$170Spirit Airlines
Find Deal
Thu, Jun 6
9:37 pm - 11:18 amORD-KIN
37h 41m2 stops
$180Spirit Airlines
Find Deal
Thu, Jun 6
5:00 am - 11:10 amORD-KIN
6h 10m1 stop
$184Spirit Airlines
Find Deal
Thu, Aug 1
9:37 pm - 11:18 amORD-KIN
13h 41m2 stops
$187Spirit Airlines
Find Deal
Thu, Jun 6
6:00 am - 7:56 pmMDW-KIN
13h 56m1 stop
$202Delta
Find Deal
Thu, Jun 6
9:37 pm - 11:10 amORD-KIN
13h 33m2 stops
$282Spirit Airlines
Find Deal
Thu, Aug 1
9:32 am - 7:56 pmMDW-KIN
10h 24m2 stops
$291Delta
Find Deal
Thu, Jun 6
11:13 am - 11:10 amORD-KIN
23h 57m3 stops
$342Spirit Airlines
Find Deal
Thu, Aug 1
8:09 am - 7:40 pmORD-KIN
11h 31m2 stops
7:30 am - 9:54 pmKIN-ORD
14h 24m2 stops
$643American Airlines
Find Deal
Sat, May 18 - Tue, May 21
12:40 pm - 7:40 pmORD-KIN
7h 00m1 stop
7:30 am - 4:10 pmKIN-ORD
8h 40m1 stop
$688American Airlines
Find Deal
Sat, May 18 - Tue, May 21
6:40 pm - 11:25 amORD-KIN
16h 45m1 stop
12:26 pm - 11:29 pmKIN-ORD
11h 03m1 stop
$746Spirit Airlines
Find Deal
Sat, May 18 - Tue, May 21
6:38 am - 7:40 pmORD-KIN
13h 02m2 stops
7:30 am - 7:21 amKIN-ORD
23h 51m2 stops
$803American Airlines
Find Deal
Sat, May 18 - Tue, May 21
5:00 am - 11:25 amORD-KIN
6h 25m1 stop
12:26 pm - 11:29 pmKIN-ORD
11h 03m1 stop
$858Spirit Airlines
Find Deal
Sat, May 18 - Tue, May 21
3:45 pm - 7:56 pmMDW-KIN
28h 11m1 stop
9:00 am - 5:06 pmKIN-MDW
32h 06m2 stops
$966Delta
Find Deal
Sat, May 18 - Tue, May 21
5:47 pm - 7:56 pmMDW-KIN
26h 09m2 stops
9:00 am - 9:06 amKIN-MDW
48h 06m2 stops
$971Delta
Find Deal
Sat, May 18 - Tue, May 21
11:01 am - 7:56 pmMDW-KIN
8h 55m1 stop
9:00 am - 7:55 amKIN-MDW
22h 55m1 stop
$1,093Delta
Find Deal
Sat, May 18 - Tue, May 21
6:00 am - 7:56 pmMDW-KIN
13h 56m1 stop
9:00 am - 10:01 pmKIN-MDW
13h 01m1 stop
$1,795Delta
Find Deal
Sat, May 18 - Tue, May 21
9:32 am - 7:56 pmMDW-KIN
10h 24m2 stops
9:00 am - 3:50 pmKIN-MDW
6h 50m1 stop
$1,800Delta
Find Deal
Sat, May 18 - Tue, May 21

Flights from Chicago to Kingston - Travel Insights & Trends

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 flights from Chicago to Kingston clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Kingston on a Tuesday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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 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 January, where tickets cost $477 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $1,113 and $638 respectively.

How far in advance should I book a flight from Chicago to Kingston?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Kingston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Kingston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 20 days before departure.

Which airlines provide the cheapest flights from Chicago to Kingston?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Spirit Airlines offered the best one-way deal for that route, at $165. KAYAK users also found Chicago to Kingston round-trip flights on Spirit Airlines from $341 and on Delta from $468.

Good to know

Low season

September

High season

March

Cheapest flight

$165
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 8% 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 $165 for a one-way ticket and $341 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 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $634 and an overall rating of 7.3.

  • 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.

See more FAQs

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 10706 reviews
8.2Boarding
8.6Crew
7.4Food
7.9Comfort
8.0Entertainment
Airline reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

2.0 MediocreDevan, May 2024AUS - BOS
Read more about Delta reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The plane was FREEZING SEATS UNCOMFORTABLE Otherwise smooth Thank you

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Arrived 3 hours early and never made it past baggage drop

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

Book cheap flights from Chicago to Kingston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Kingston found on KAYAK in the last 72 hours.
6/6Thu
1 stopSpirit Airlines
16h 38mORD-KIN
$165
6/6Thu
1 stopSpirit Airlines
16h 38mORD-KIN
$170
6/6Thu
2 stopsSpirit Airlines
37h 41mORD-KIN
$180
8/1Thu
1 stopSpirit Airlines
6h 10mORD-KIN
$184
6/6Thu
2 stopsSpirit Airlines
13h 41mORD-KIN
$187
6/6Thu
1 stopDelta
13h 56mMDW-KIN
$202
8/1Thu
2 stopsSpirit Airlines
13h 33mORD-KIN
$282
6/6Thu
2 stopsDelta
10h 24mMDW-KIN
$291
8/1Thu
3 stopsSpirit Airlines
23h 57mORD-KIN
$342

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Last minute flights from Chicago to Kingston

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Kingston that are departing in the next 10 days.
5/18Sat
multi-stopAmerican Airlines
11h 31mORD-KIN
5/21Tue
multi-stopAmerican Airlines
14h 24mKIN-ORD
$643
5/18Sat
multi-stopAmerican Airlines
7h 00mORD-KIN
5/21Tue
multi-stopAmerican Airlines
8h 40mKIN-ORD
$688
5/18Sat
multi-stopSpirit Airlines
16h 45mORD-KIN
5/21Tue
multi-stopSpirit Airlines
11h 03mKIN-ORD
$746
5/18Sat
multi-stopAmerican Airlines
13h 02mORD-KIN
5/21Tue
multi-stopAmerican Airlines
23h 51mKIN-ORD
$803
5/18Sat
multi-stopSpirit Airlines
6h 25mORD-KIN
5/21Tue
multi-stopSpirit Airlines
11h 03mKIN-ORD
$858
5/18Sat
multi-stopDelta
28h 11mMDW-KIN
5/21Tue
multi-stopDelta
32h 06mKIN-MDW
$966
5/18Sat
multi-stopDelta
26h 09mMDW-KIN
5/21Tue
multi-stopDelta
48h 06mKIN-MDW
$971
5/18Sat
multi-stopDelta
8h 55mMDW-KIN
5/21Tue
multi-stopDelta
22h 55mKIN-MDW
$1,093
5/18Sat
multi-stopDelta
13h 56mMDW-KIN
5/21Tue
multi-stopDelta
13h 01mKIN-MDW
$1,795
5/18Sat
multi-stopDelta
10h 24mMDW-KIN
5/21Tue
multi-stopDelta
6h 50mKIN-MDW
$1,800

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Flights to Kingston

Destination:

Kingston (KIN)Jamaica

Cabin classes:

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