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$225+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
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 February 13, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:00 pm
KIN
-
ORD
1 stop7h 48m
Spirit Airlines
Wed 5/275:32 pm
ORD
-
KIN
1 stop17h 33m
Spirit Airlines
Deal found 2/10$355
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:00 pm
KIN
-
ORD
1 stop7h 48m
Spirit Airlines
Mon 5/185:32 pm
ORD
-
KIN
1 stop17h 33m
Spirit Airlines
Deal found 2/10$370
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:00 pm
KIN
-
ORD
1 stop7h 48m
Spirit Airlines
Sat 5/305:32 pm
ORD
-
KIN
1 stop17h 33m
Spirit Airlines
Deal found 2/10$377
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:00 pm
KIN
-
ORD
1 stop7h 48m
Spirit Airlines
Tue 5/261:35 pm
ORD
-
KIN
2 stops21h 30m
Spirit Airlines
Deal found 2/10$382
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:00 pm
KIN
-
ORD
2 stops19h 59m
Spirit Airlines
Mon 8/315:32 pm
ORD
-
KIN
1 stop17h 33m
Spirit Airlines
Deal found 2/10$410
This Air Canada deal was found by Cheapflights users on 2/12. 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
2 stops21h 12m
Air Canada
Wed 5/276:23 pm
ORD
-
KIN
2 stops19h 32m
Air Canada
Deal found 2/12$424
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Thu 2/191:17 pm
KIN
-
ORD
1 stop11h 30m
Spirit Airlines
Sat 2/288:16 pm
ORD
-
KIN
1 stop14h 59m
Spirit Airlines
Deal found 2/11$444
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:11 pm
KIN
-
ORD
1 stop10h 46m
Multiple Airlines
Mon 8/3111:26 am
ORD
-
KIN
2 stops23h 34m
Multiple Airlines
Deal found 2/12$449

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 February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$355
(Cheapflightsfares)

One-way from

$225
(OneTravel)

Popular in

December

Cheapest in

March

Average price

$504
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. 2% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 13, 2026.
Use the filters below to find and compare flights from Kingston to Chicago that are best for you.

Fly from

Kingston

Fly to

Chicago

Route

Depart

Return

Price

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/13

12:00 pm-7:48 pm

1 stop7h 48m

Chicago O'Hare Intl

Wed 5/27

5:32 pm-11:05 am

1 stop17h 33m

$355

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/13

12:00 pm-7:48 pm

1 stop7h 48m

Chicago O'Hare Intl

Tue 5/26

5:32 pm-11:05 am

1 stop17h 33m

$355

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 5/14

12:00 pm-7:48 pm

1 stop7h 48m

Chicago O'Hare Intl

Mon 5/18

5:32 pm-11:05 am

1 stop17h 33m

$370

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 5/19

12:00 pm-7:48 pm

1 stop7h 48m

Chicago O'Hare Intl

Mon 8/31

5:32 pm-11:05 am

1 stop17h 33m

$370

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 5/16

12:00 pm-7:48 pm

1 stop7h 48m

Chicago O'Hare Intl

Sat 5/30

5:32 pm-11:05 am

1 stop17h 33m

$377

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/6

12:11 pm-7:47 pm

1 stop7h 36m

$225

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 5/9

12:11 pm-7:47 pm

1 stop7h 36m

$243

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 5/5

12:11 pm-8:03 am

2 stops19h 52m

$255

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 5/11

12:11 pm-12:14 am

1 stop12h 03m

$259

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 5/4

12:11 pm-8:03 am

2 stops19h 52m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 11 results
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 February.
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, October is the cheapest month in which you can book a flight from Kingston to Chicago (average of $289). Flying from Kingston to Chicago in April is currently the most expensive (average of $483). 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.

How much does it cost to fly round-trip from Kingston to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 13, 2026.
See what other customers who have flown with Delta and American Airlines from Kingston to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,193 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,193 reviews
Delta
7.9
Good
8,193 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,278 reviews
Delta
7.9
Good
8,193 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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

  • How long is the flight from Kingston to Chicago?

    Spirit Airlines can get you from Kingston to Chicago in just under 7h 48m. Your travel time can differ by up to . There are 1785 mi between Kingston and Chicago.

  • What are the cheapest airlines flying from Kingston to Chicago round-trip?

    Cheapflights users have booked flights from Kingston to Chicago round-trip from $316. Another airline that can offer you cheap pricing is American Airlines. Spirit Airlines is priced at 40% lower than the current average price of a flight leaving 3 months from now.

  • 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, October is the cheapest month in which you can book a flight from Kingston to Chicago (average of $289). Flying from Kingston to Chicago in April is currently the most expensive (average of $483). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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.
Kingston to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Montego Bay to Midway flights

Top 2 airlines flying from Kingston to Chicago

Discover the top 2 airlines 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 February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$415Average$518FlexibilityNo cancel feeOn-time71%

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