CHI - KIN

$211 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 5/15. 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
$500
Typical prices: $792-$556
Spirit Airlines, Air Canada
Wed 5/20Mon 5/25
ORD - KIN • 1 stop
Cheapest one-way
$211
Typical prices: $240-$258
Spirit Airlines
Fri 5/15
ORD - KIN • 1 stop
Top airlines
Cheapest • from $508 (round-trip)
Best reviews • 7.1 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 $447 (round-trip)
Shortest trip • 6h 18m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 76% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, May 20 - Mon, May 25
Multiple Airlines Logo
5:05 am - 11:07 am
ORD
-
KIN
6h 02m
1 stop
Multiple Airlines Logo
3:05 pm - 9:00 am
KIN
-
ORD
17h 55m
1 stop
$500Multiple Airlines
Wed, May 20 - Mon, May 25
Multiple Airlines Logo
5:05 am - 11:07 am
ORD
-
KIN
6h 02m
1 stop
Multiple Airlines Logo
3:05 pm - 7:45 am
KIN
-
ORD
16h 40m
2 stops
$505Multiple Airlines
Mon, Jun 1 - Wed, Jun 10
Multiple Airlines Logo
10:00 am - 1:55 pm
ORD
-
KIN
27h 55m
1 stop
Multiple Airlines Logo
12:12 pm - 11:15 pm
KIN
-
ORD
11h 03m
1 stop
$507Multiple Airlines
Mon, Jun 8 - Wed, Jun 17
Air Canada Logo
8:20 pm - 1:55 pm
ORD
-
KIN
17h 35m
1 stop
Air Canada Logo
3:05 pm - 2:55 pm
KIN
-
ORD
23h 50m
1 stop
$508Air Canada
Mon, May 11 - Fri, May 15
Air Canada Logo
3:50 pm - 1:55 pm
ORD
-
KIN
22h 05m
1 stop
Air Canada Logo
3:05 pm - 2:55 pm
KIN
-
ORD
23h 50m
1 stop
$509Air Canada
Fri, Jun 19 - Fri, Jun 26
Spirit Airlines Logo
5:10 am - 11:55 am
ORD
-
KIN
6h 45m
1 stop
Spirit Airlines Logo
1:00 pm - 11:59 pm
KIN
-
ORD
10h 59m
1 stop
$512Spirit Airlines
Thu, Jun 4 - Mon, Jun 8
Spirit Airlines Logo
7:33 pm - 11:07 am
ORD
-
KIN
15h 34m
1 stop
Spirit Airlines Logo
12:12 pm - 11:15 pm
KIN
-
ORD
11h 03m
1 stop
$522Spirit Airlines
Sat, Sep 19 - Sat, Sep 26
Delta Logo
10:35 am - 7:30 pm
MDW
-
KIN
8h 55m
1 stop
Delta Logo
9:00 am - 9:46 pm
KIN
-
MDW
12h 46m
1 stop
$576Delta
Sat, Sep 19 - Sat, Sep 26
Delta Logo
10:35 am - 7:30 pm
MDW
-
KIN
8h 55m
1 stop
Delta Logo
9:00 am - 6:31 pm
KIN
-
MDW
9h 31m
2 stops
$581Delta
Thu, May 14 - Thu, May 21
KLM Logo
6:23 am - 8:00 pm
MDW
-
KIN
13h 37m
1 stop
KLM Logo
9:00 am - 9:09 pm
KIN
-
MDW
12h 09m
1 stop
$648KLM
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 May.

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 April and July, where the average cost of round-trip tickets is $556 and $471 respectively.

Good to know

Low seasonNovember
Cheapest flight$211
Best time to beat the crowds but there is an average 58% increase in price.
Most popular time to fly and prices are also 26% 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 $211 for a one-way ticket and $500 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, American Airlines or Spirit Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Kingston are American Airlines and Spirit Airlines. With an average price for the route of $656 and an overall rating of 7.1, American Airlines is the most popular choice. Spirit Airlines is also a great choice for the route, with an average price of $467 and an overall rating of 6.3.

  • 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.

Reviews of the top airlines 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 11676 reviews
6.9Entertainment
7.2Comfort
7.5Boarding
6.4Food
7.9Crew
Airline reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

2.0 MediocreStella, Apr 2026
ORD - DCA
Read more American Airlines reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

The flight was delayed for over an hour. No one at the gate said anything about the flight being delayed. I had to rely on my phone for updates. Absolutely no communication at the gate.

The AC broke and we were onboard for 2 hrs waiting for them to fix it. It was so hot and we could not get any water or anything to drink. They finally let us off the plane after the second attempt and we boarded a new plane. We didn't land till 12:15am!

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

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.

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

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

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

Information on your arrival and departure airports