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CHI - KIN

$137 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
sex 6/7
sex 6/14

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 43,968,530 times on KAYAK, and here is why:

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

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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Cheap flight deals 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 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
$321Spirit Airlines
Find Deal
seg, jun 3 - qui, jun 6
9:25 pm - 11:25 amORD-KIN
14h 00m2 stops
12:26 pm - 12:55 amKIN-ORD
12h 29m1 stop
$342Spirit Airlines
Find Deal
seg, jun 3 - qui, jun 6
6:40 pm - 11:18 amORD-KIN
16h 38m1 stop
12:26 pm - 12:55 amKIN-ORD
12h 29m1 stop
$347Spirit Airlines
Find Deal
qui, jun 6 - qui, jun 13
6:00 am - 7:56 pmMDW-KIN
13h 56m1 stop
9:00 am - 10:01 pmKIN-MDW
13h 01m1 stop
$480Delta
Find Deal
seg, jun 3 - qui, jun 6
9:30 am - 7:47 pmORD-KIN
10h 17m1 stop
9:00 am - 9:04 pmKIN-ORD
12h 04m1 stop
$480Delta
Find Deal
sáb, out 12 - seg, out 14
6:40 pm - 11:25 amORD-KIN
16h 45m1 stop
12:30 pm - 10:01 amKIN-ORD
21h 31m2 stops
ter, mai 21 - ter, mai 28
8:20 am - 6:21 pmORD-KIN
10h 01m2 stops
7:32 am - 6:00 pmKIN-ORD
10h 28m2 stops
$483American Airlines
Find Deal
qua, out 23 - qua, out 30
5:00 am - 11:25 amORD-KIN
6h 25m1 stop
7:00 pm - 9:55 amKIN-ORD
38h 55m2 stops
ter, mai 21 - seg, mai 27
6:00 am - 11:25 amORD-KIN
29h 25m1 stop
12:30 pm - 7:58 amKIN-ORD
19h 28m2 stops
$597Air Canada
Find Deal
qui, mai 23 - seg, mai 27
7:25 am - 7:46 pmORD-KIN
12h 21m2 stops
7:44 am - 9:24 pmKIN-ORD
13h 40m2 stops
$660American Airlines
Find Deal
dom, ago 25 - dom, set 1

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 $137. KAYAK users also found Chicago to Kingston round-trip flights on Spirit Airlines from $321 and on Delta from $480.

Good to know

Low season

May

High season

March

Cheapest flight

$137
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 9% 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 $137 for a one-way ticket and $321 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 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 $529 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 10789 reviews
8.6Crew
7.9Comfort
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

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

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

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.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

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.

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!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

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.
6/6qui
1 stopSpirit Airlines
16h 38mORD-KIN
$137
6/6qui
2 stopsSpirit Airlines
29h 58mORD-KIN
$166
6/6qui
1 stopDelta
13h 56mMDW-KIN
$232
5/21ter
1 stopAir Canada
29h 25mORD-KIN
$668
5/21ter
2 stopsAir Canada
26h 40mORD-KIN
$843

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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.
5/12dom
multi-stop
26h 40mORD-KIN
5/18sáb
multi-stop
19h 47mKIN-ORD
$567
5/12dom
multi-stopSpirit Airlines
16h 45mORD-KIN
5/18sáb
multi-stopSpirit Airlines
20h 29mKIN-ORD
$597
5/12dom
multi-stop
26h 40mORD-KIN
5/18sáb
multi-stop
23h 08mKIN-ORD
$627
5/11sáb
multi-stopSpirit Airlines
6h 25mORD-KIN
5/14ter
multi-stopSpirit Airlines
11h 03mKIN-ORD
$643
5/11sáb
multi-stopSpirit Airlines
16h 45mORD-KIN
5/14ter
multi-stopSpirit Airlines
32h 09mKIN-ORD
$681
5/11sáb
multi-stopSpirit Airlines
16h 18mORD-KIN
5/14ter
multi-stopSpirit Airlines
32h 09mKIN-ORD
$745
5/11sáb
multi-stopDelta
8h 55mMDW-KIN
5/14ter
multi-stopDelta
13h 01mKIN-MDW
$801
5/11sáb
multi-stopDelta
10h 24mMDW-KIN
5/14ter
multi-stopDelta
13h 01mKIN-MDW
$911
5/12dom
multi-stopDelta
13h 56mMDW-KIN
5/18sáb
multi-stopDelta
22h 55mKIN-MDW
$925
5/12dom
multi-stopDelta
10h 24mMDW-KIN
5/18sáb
multi-stopDelta
22h 55mKIN-MDW
$930

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Flights to Kingston

Destination:

Kingston (KIN)Jamaica

Cabin classes:

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