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$332+ Cheap flights from Kingston (KIN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheap flight deals from Kingston to Chicago

Cheapest flights from Kingston to Chicago
Explore the most affordable flight options available from Kingston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 10, 2026.

This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/79:00 am
KIN
-
ORD
1 stop14h 59m
Delta
Sat 6/139:00 am
ORD
-
KIN
1 stop11h 00m
Delta
Deal found 5/8$531
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:00 am
KIN
-
ORD
2 stops23h 45m
Delta
Fri 6/57:07 am
ORD
-
KIN
1 stop12h 53m
Delta
Deal found 5/8$538
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:06 pm
KIN
-
ORD
1 stop16h 04m
American Airlines
Wed 6/37:00 am
ORD
-
KIN
1 stop12h 54m
American Airlines
Deal found 5/6$540
This Cheapflightsfares deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2711:59 pm
KIN
-
ORD
1 stop9h 55m
JetBlue
Wed 6/36:15 am
ORD
-
KIN
1 stop16h 33m
JetBlue
Deal found 5/9$549
This FlightHub deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
KIN
-
ORD
1 stop7h 39m
JetBlue
Tue 9/16:27 pm
ORD
-
KIN
1 stop29h 20m
JetBlue
Deal found 5/10$568
This Cheapflightsfares deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:15 pm
KIN
-
ORD
1 stop18h 01m
JetBlue
Fri 5/2910:45 am
ORD
-
KIN
1 stop12h 03m
JetBlue
Deal found 5/7$573
This Air Canada deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:05 pm
KIN
-
ORD
1 stop17h 55m
Air Canada
Tue 5/268:35 pm
ORD
-
KIN
1 stop17h 20m
Air Canada
Deal found 5/7$576
This Cheapflightsfares deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:59 pm
KIN
-
ORD
1 stop14h 17m
JetBlue
Fri 9/42:35 pm
ORD
-
KIN
1 stop6h 45m
JetBlue
Deal found 5/9$581
This Expedia deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:05 pm
KIN
-
ORD
1 stop23h 50m
Air Canada
Tue 9/88:40 pm
ORD
-
KIN
1 stop17h 15m
Air Canada
Deal found 5/7$582

Find flight deals from Kingston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Kingston (KIN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$531
(Delta)

One-way from

$332
(Delta)

Popular in

April

Cheapest in

January

Average price

$767
Provider with most accurate pricing for Kingston Norman Manley-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Kingston Norman Manley-Chicago (CHI) flights.
Search Deals
From Kingston Norman Manley to Chicago (CHI)
Search Deals
One-way flight from Kingston Norman Manley to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($199 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kingston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 10, 2026.
Use the filters below to find and compare flights from Kingston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 6/2

9:00 am-8:26 pm

1 stop11h 26m

Chicago O'Hare Intl

Fri 6/5

5:30 am-8:00 pm

1 stop14h 30m

$531

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 6/7

9:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Sun 6/14

6:35 am-8:00 pm

1 stop13h 25m

$531

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 6/7

9:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Sat 6/13

9:00 am-8:00 pm

1 stop11h 00m

$531
Quickest round-trip

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/27

12:41 pm-12:42 am

2 stops12h 01m

Chicago O'Hare Intl

Wed 6/3

10:00 am-7:54 pm

2 stops9h 54m

$544

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/22

11:59 pm-2:16 pm

1 stop14h 17m

Chicago O'Hare Intl

Fri 5/29

10:45 am-10:48 pm

1 stop12h 03m

$595

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 5/25

9:00 am-8:14 pm

2 stops11h 14m

Chicago O'Hare Intl

Tue 9/1

7:10 am-8:04 pm

1 stop12h 54m

$615

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 6/11

9:00 am-6:29 pm

2 stops9h 29m

Chicago O'Hare Intl

Tue 6/16

6:35 am-8:00 pm

1 stop13h 25m

$615

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/22

9:00 am-8:14 pm

2 stops11h 14m

Chicago O'Hare Intl

Fri 5/29

7:07 am-8:00 pm

1 stop12h 53m

$615

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/29

3:05 pm-9:00 am

1 stop17h 55m

Chicago O'Hare Intl

Mon 6/1

6:04 pm-1:55 pm

2 stops19h 51m

$630
Cheapest one-way

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/27

9:00 am-8:26 pm

1 stop11h 26m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Compare providers for flights from Kingston to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Kingston to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Kingston-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kingston-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Kingston-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kingston-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Kingston-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Kingston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kingston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Kingston to Chicago?

Currently, May is the cheapest month in which you can book a flight from Kingston to Chicago (average of $343). Flying from Kingston to Chicago in April is currently the most expensive (average of $728). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What’s the top layover airport for flights from Kingston to Chicago?

Share of 1-stop round-trip flights from Kingston to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Fort Lauderdale (FLL) – chosen by Cheapflights users on 75% of 1-stop itineraries from Kingston to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Kingston to Chicago?

Average round-trip fare for 1-stop flights from Kingston to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Miami (MIA) is the most affordable 1-stop option, with an average round-trip price of $448.

What’s the fastest layover option from Kingston to Chicago?

Shortest average travel time for 1-stop one-way flights from Kingston to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 7h 19m.

Which airport typically offers the quickest layover for flights from Kingston to Chicago?

Average layover duration for 1-stop one-way flights from Kingston to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Miami (MIA) offer the fastest connection on this route, with an average layover time of 3h 04m.

Related info for your journey

Find useful and relevant information for your journey from Kingston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Kingston to Chicago?

    For a flight from Kingston to Chicago, you will be flying from Norman Manley. Kingston Norman Manley (KIN) is just 5.1 mi from the center of the city. Norman Manley is the only Kingston airport and it handles 0 outbound flights to Chicago per day. 1 airline has flights to Chicago from Kingston Norman Manley on a regular basis.

  • How long is the flight from Kingston to Chicago?

    Delta and American Airlines can get you from Kingston to Chicago in just under 11h 26m. Your travel time can differ by up to 35m. There are 1785 mi between Kingston and Chicago. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Kingston to Chicago round-trip?

    Cheapflights users have booked flights from Kingston to Chicago round-trip from $415. American Airlines is priced at 29% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Kingston to Chicago one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $241. Users have also found prices from $259 and $268 on American Airlines and Delta, respectively.

  • Can I find deals for flights from Kingston to Chicago that include hotel bookings?

    Yes. In addition to deals on Kingston to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kingston to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kingston to Chicago.

  • Can I find deals for business class flights from Kingston to Chicago?

    Yes. Cheapflights offers flight deals from Kingston to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kingston to Chicago?

    Currently, May is the cheapest month in which you can book a flight from Kingston to Chicago (average of $343). Flying from Kingston to Chicago in April is currently the most expensive (average of $728). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Kingston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Montego Bay to O'Hare Intl flights
Kingston to O'Hare Intl flights

Top airline flying from Kingston to Chicago

Discover the top airline that operate flights from Kingston to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$415Average$543FlexibilityNo cancel feeOn-time71%

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