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$268+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
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 June 24, 2026.

This American Airlines deal was found by Cheapflights users on 6/24. 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.
Tue 7/78:00 am
KIN
-
ORD
1 stop11h 53m
American Airlines
Thu 8/66:45 am
ORD
-
KIN
2 stops9h 39m
American Airlines
Deal found 6/24$425
This American Airlines deal was found by Cheapflights users on 6/23. 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.
Sat 7/44:55 pm
KIN
-
ORD
1 stop7h 31m
American Airlines
Tue 8/186:59 am
ORD
-
KIN
1 stop6h 00m
American Airlines
Deal found 6/23$430
This Cheapflightsfares deal was found by Cheapflights users on 6/24. 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 7/1512:08 pm
KIN
-
ORD
1 stop11h 36m
JetBlue
Sat 7/252:35 pm
ORD
-
KIN
1 stop6h 42m
JetBlue
Deal found 6/24$467
This American Airlines deal was found by Cheapflights users on 6/24. 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 7/1512:40 pm
KIN
-
ORD
2 stops11h 21m
American Airlines
Sat 7/255:00 am
ORD
-
KIN
2 stops10h 55m
American Airlines
Deal found 6/24$491
This American Airlines deal was found by Cheapflights users on 6/22. 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.
Thu 7/26:21 am
KIN
-
ORD
1 stop17h 09m
American Airlines
Sat 7/112:19 pm
ORD
-
KIN
1 stop5h 53m
American Airlines
Deal found 6/22$497
This JetBlue deal was found by Cheapflights users on 6/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:55 pm
KIN
-
ORD
1 stop9h 49m
JetBlue
Tue 8/186:00 am
ORD
-
KIN
1 stop14h 17m
JetBlue
Deal found 6/23$504
This Delta deal was found by Cheapflights users on 6/21. 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 8/49:13 am
KIN
-
ORD
2 stops11h 17m
Delta
Tue 8/117:00 am
ORD
-
KIN
2 stops13h 13m
Delta
Deal found 6/21$506

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 June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$421
(American Airlines)

One-way from

$268
(American Airlines)
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)
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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 June 24, 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 7/7

8:00 am-7:26 pm

2 stops11h 26m

Chicago O'Hare Intl

Thu 8/6

6:45 am-4:24 pm

2 stops9h 39m

$491

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 7/15

12:40 pm-10:01 pm

1 stop9h 21m

Chicago O'Hare Intl

Sat 7/25

5:00 am-3:55 pm

2 stops10h 55m

$491

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 8/4

9:13 am-8:30 pm

2 stops11h 17m

Chicago O'Hare Intl

Tue 8/11

7:00 am-8:13 pm

2 stops13h 13m

$506

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 8/4

2:56 pm-1:59 pm

1 stop23h 03m

Chicago O'Hare Intl

Sat 10/24

3:20 pm-1:58 pm

1 stop22h 38m

$535

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 9/1

6:00 am-1:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Tue 9/1

6:27 pm-11:47 pm

1 stop29h 20m

$539

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 7/24

12:40 pm-12:29 am

2 stops11h 49m

Chicago O'Hare Intl

Sun 8/2

5:00 am-4:03 pm

2 stops11h 03m

$540
Quickest round-trip

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 7/9

1:55 pm-11:44 pm

1 stop9h 49m

Chicago O'Hare Intl

Mon 8/17

7:00 am-12:45 pm

1 stop5h 45m

$548

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 7/11

1:55 pm-11:44 pm

1 stop9h 49m

Chicago O'Hare Intl

Sat 8/15

9:40 am-11:21 pm

1 stop13h 41m

$552
Cheapest one-way
Quickest one-way

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 8/28

9:13 am-6:29 pm

2 stops9h 16m

$277

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 7/19

6:20 am-12:26 am

1 stop18h 06m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 13 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 June.
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
No data available for this route at this time. Please check back soon.

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. 0 airlines have flights to Chicago from Kingston Norman Manley on a regular basis.

  • How long is the flight from Kingston to Chicago?

    American Airlines and Delta can get you from Kingston to Chicago in just under 11h 17m. Your travel time can differ by up to 09m. There are 1785 mi between Kingston and Chicago. This flight may include one or multiple stops.

  • 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.

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.
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