HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$245+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kingston to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 27, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 4/223:18 pm
KIN
-
ORD
1 stop9h 06m
Spirit Airlines
Wed 4/295:05 am
ORD
-
KIN
1 stop9h 07m
Spirit Airlines
Deal found 3/25$348
This Expedia deal was found by Cheapflights users on 3/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:18 pm
KIN
-
ORD
1 stop9h 09m
Spirit Airlines
Wed 5/135:05 am
ORD
-
KIN
1 stop9h 07m
Spirit Airlines
Deal found 3/22$367
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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.
Fri 5/83:18 pm
KIN
-
ORD
1 stop18h 13m
Spirit Airlines
Mon 5/115:05 am
ORD
-
KIN
1 stop9h 07m
Spirit Airlines
Deal found 3/24$378
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Wed 4/223:18 pm
KIN
-
ORD
2 stops20h 14m
Multiple Airlines
Wed 4/295:05 am
ORD
-
KIN
1 stop9h 07m
Multiple Airlines
Deal found 3/25$419
This Air Canada deal was found by Cheapflights users on 3/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:35 am
KIN
-
ORD
2 stops24h 42m
Air Canada
Mon 5/118:20 pm
ORD
-
KIN
1 stop17h 35m
Air Canada
Deal found 3/22$429
This Air Canada deal was found by Cheapflights users on 3/22. 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 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 stop18h 00m
Air Canada
Wed 5/278:20 pm
ORD
-
KIN
1 stop14h 05m
Air Canada
Deal found 3/22$435
This Air Canada deal was found by Cheapflights users on 3/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/253:05 pm
KIN
-
ORD
1 stop18h 00m
Air Canada
Tue 9/18:40 pm
ORD
-
KIN
1 stop17h 15m
Air Canada
Deal found 3/22$436
This Air Canada deal was found by Cheapflights users on 3/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:05 pm
KIN
-
ORD
2 stops19h 13m
Air Canada
Wed 5/138:20 pm
ORD
-
KIN
1 stop14h 05m
Air Canada
Deal found 3/22$438
This Justfly.com deal was found by Cheapflights users on 3/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:18 pm
KIN
-
ORD
1 stop9h 09m
Spirit Airlines
Wed 5/275:05 am
ORD
-
KIN
1 stop9h 07m
Spirit Airlines
Deal found 3/24$439
This Air Canada deal was found by Cheapflights users on 3/22. 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 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
Tue 5/268:20 pm
ORD
-
KIN
1 stop17h 35m
Air Canada
Deal found 3/22$440

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 March 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$348
(Cheapflightsfares)

One-way from

$245
(FlightHub)

Popular in

December

Cheapest in

January
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. 0% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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 March 27, 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
Quickest round-trip

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/15

3:18 pm-12:27 am

1 stop9h 09m

Chicago O'Hare Intl

Fri 5/29

5:05 am-2:12 pm

1 stop9h 07m

$444

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/13

3:05 pm-10:18 am

2 stops19h 13m

Chicago O'Hare Intl

Wed 5/27

8:20 pm-10:25 am

1 stop14h 05m

$450

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/15

3:05 pm-7:58 am

2 stops16h 53m

Chicago O'Hare Intl

Tue 5/19

6:21 pm-1:55 pm

2 stops19h 34m

$503

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 5/16

9:00 am-8:24 pm

1 stop11h 24m

Chicago O'Hare Intl

Sat 5/30

7:00 am-8:00 pm

2 stops13h 00m

$511

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 5/14

9:00 am-8:14 pm

2 stops11h 14m

Chicago O'Hare Intl

Mon 5/18

5:30 am-8:00 pm

1 stop14h 30m

$511
Cheapest one-way

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/15

12:12 pm-11:59 pm

1 stop11h 47m

$251

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 5/5

3:05 pm-9:05 am

1 stop18h 00m

$276

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/6

3:05 pm-9:05 am

1 stop18h 00m

$288

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/27

3:05 pm-9:05 am

1 stop18h 00m

$288

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 5/12

3:05 pm-10:18 am

2 stops19h 13m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 12 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 March.
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, April is the cheapest month in which you can book a flight from Kingston to Chicago (average of $184). Flying from Kingston to Chicago in January is currently the most expensive (average of $448). 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.

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 March 27, 2026.
See what other customers who have flown with 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.
American Airlines
7.1
Good
11,507 reviews

Entertainment

6.9

Comfort

7.2

Overall

7.1

Crew

7.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,507 reviews
American Airlines
7.1
Good
11,507 reviews

Entertainment

6.9

Comfort

7.2

Overall

7.1

Crew

7.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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, Air Canada, and Delta can get you from Kingston to Chicago in just under 9h 09m. Your travel time can differ by up to 10h 04m. There are 1785 mi between Kingston and Chicago. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Kingston to Chicago round-trip from $380. Another airline that can offer you cheap pricing is American Airlines. Spirit Airlines is priced at 29% 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, April is the cheapest month in which you can book a flight from Kingston to Chicago (average of $184). Flying from Kingston to Chicago in January is currently the most expensive (average of $448). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 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 March 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$380Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$391Average$536FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.