CHI - KIN

$154 Find Cheap Flights from Chicago to Kingston - Compare and Save

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 9/12. 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

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Everything you should know

Cheapest round-trip
$390
Typical prices: $501-$654
JetBlue
Tue 9/22Fri 9/25
ORD - KIN • 1 stop
Cheapest one-way
$154
Typical prices: $178-$277
American Airlines
Sat 9/12
ORD - KIN • 1 stop
Top airlines
Cheapest • from $390 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Chicago and Kingston. You'll need at least 1 connection.
Insights
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Insights
Top layover airports
Cheapest • Avg $563 (round-trip)
Shortest trip • 5h 44m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 74% price drop
Most popular
Good to know
Good to know
+1
+1
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Good to know
+1
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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, Sep 22 - Fri, Sep 25
JetBlue Logo
6:00 am - 12:09 pm
ORD
-
KIN
6h 09m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
KIN
-
ORD
8h 26m
1 stop
$390JetBlue
Wed, Oct 7 - Sat, Oct 17
American Airlines Logo
6:59 am - 3:58 pm
ORD
-
KIN
8h 59m
1 stop
American Airlines Logo
5:03 pm - 7:42 am
KIN
-
ORD
14h 39m
1 stop
$398American Airlines
Wed, Oct 7 - Sat, Oct 17
American Airlines Logo
6:59 am - 3:58 pm
ORD
-
KIN
8h 59m
1 stop
American Airlines Logo
11:58 am - 10:30 pm
KIN
-
ORD
10h 32m
2 stops
$403American Airlines
Wed, Sep 2 - Wed, Sep 16
JetBlue Logo
7:00 am - 12:45 pm
ORD
-
KIN
5h 45m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
KIN
-
ORD
8h 26m
1 stop
$410JetBlue
Sun, Sep 20 - Thu, Sep 24
JetBlue Logo
6:00 am - 12:09 pm
ORD
-
KIN
6h 09m
1 stop
JetBlue Logo
1:50 pm - 11:31 pm
KIN
-
ORD
9h 41m
1 stop
$417JetBlue
Sun, Sep 20 - Fri, Sep 25
JetBlue Logo
6:00 am - 12:09 pm
ORD
-
KIN
6h 09m
1 stop
JetBlue Logo
1:50 pm - 11:31 pm
KIN
-
ORD
9h 41m
1 stop
$425JetBlue
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
8:37 am - 4:24 pm
ORD
-
KIN
7h 47m
1 stop
American Airlines Logo
2:00 pm - 11:52 pm
KIN
-
ORD
9h 52m
2 stops
$430American Airlines
Fri, Aug 14 - Fri, Aug 21
Delta Logo
12:46 pm - 8:13 pm
MDW
-
KIN
7h 27m
1 stop
Delta Logo
9:13 am - 10:36 pm
KIN
-
MDW
13h 23m
1 stop
$464Delta
Tue, Sep 22 - Fri, Sep 25
Delta Logo
9:29 am - 8:10 pm
MDW
-
KIN
10h 41m
2 stops
Delta Logo
9:10 am - 4:16 pm
KIN
-
MDW
7h 06m
1 stop
$469Delta
Sat, Aug 15 - Sat, Aug 22
Delta Logo
10:56 am - 8:13 pm
MDW
-
KIN
9h 17m
1 stop
Delta Logo
9:13 am - 10:36 pm
KIN
-
MDW
13h 23m
1 stop
$550Delta
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.

How much is a round-trip flight from Chicago to Kingston?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Kingston departing in September.

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 December, where tickets cost $84 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is $471 and $433 respectively.

Good to know

Low seasonJanuary
Cheapest flight$154
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 3% 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 5 days, the lowest price for a flight from Chicago to Kingston was $154 for a one-way ticket and $390 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.

  • 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 airline flying 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.
7.1
American AirlinesOverall score based on 11769 reviews
7.5Boarding
6.8Entertainment
6.4Food
7.2Comfort
7.9Crew
Airline reviews

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

2.0 MediocreOnkar Pravin, Jul 2026
ORD - DFW
Read more American Airlines reviews

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

Nothing exceptional. No drink of any type, even in first class was provided for the hour and half trip.

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

Information on your arrival and departure airports