How long is the flight from Kingston to Chicago?

Air Canada, Copa Airlines, and American Airlines can get you from Kingston to Chicago in just under 10h 13m. Your travel time can differ by up to 13h 39m. 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 $400. Another airline that can offer you cheap pricing is JetBlue. American Airlines is priced at 30% 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 American Airlines. According to our data, you can fly for as low as $259. Users have also found prices from $266 and $268 on JetBlue and Delta, respectively.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest time of day to fly from KIN to CHI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kingston to Chicago as you normally would.

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.

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.

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.

$251+ Cheap Flights from Kingston to Chicago

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Cheap flight deals from Kingston to Chicago

Cheapest

Best

Last-minute

One-way

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 September 22, 2026.

Thu 10/13:05 pm -

2 stops19h 07m

Mon 10/58:40 pm -

1 stop17h 15m

Deal found 9/22

$404

Wed 9/233:05 pm -

1 stop17h 55m

Sun 9/278:40 pm -

1 stop17h 15m

Deal found 9/19

$421

Thu 9/2411:35 am -

1 stop25h 53m

Sat 9/263:40 pm -

2 stops46h 15m

Deal found 9/20

$423

Mon 9/213:05 pm -

2 stops19h 10m

Wed 9/235:53 pm -

1 stop16h 32m

Deal found 9/20

$425

Best flights from Kingston to Chicago
Discover carefully curated flight deals from Kingston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.

Thu 11/124:00 pm -

1 stop29h 48m

Thu 11/268:40 pm -

1 stop13h 55m

Deal found 9/20

$447

Thu 11/127:08 am -

2 stops10h 04m

Thu 11/267:00 am -

2 stops11h 42m

Deal found 9/20

$454

Thu 11/52:58 pm -

1 stop10h 13m

Thu 11/122:13 pm -

1 stop22h 39m

Deal found 9/21

$478

Fri 10/163:05 pm -

1 stop17h 55m

Thu 10/228:40 pm -

1 stop17h 50m

Deal found 9/18

$637

Tue 10/135:03 pm -

1 stop14h 44m

Thu 11/125:00 am -

1 stop16h 26m

Deal found 9/18

$506

Tue 10/133:05 pm -

1 stop22h 18m

Thu 11/1212:50 pm -

1 stop21h 45m

Deal found 9/18

$523

Sat 10/38:06 pm -

1 stop26h 04m

Tue 10/68:40 pm -

1 stop17h 15m

Deal found 9/21

$644

Fri 10/163:05 pm -

1 stop17h 55m

Thu 10/221:55 pm -

2 stops24h 00m

Deal found 9/18

$609

Last-minute flights from Kingston to Chicago
Discover last-minute flight deals from Kingston to Chicago. Data last updated September 22, 2026 and is based on user searches.

Wed 9/233:05 pm -

1 stop17h 55m

Sun 9/278:40 pm -

1 stop17h 15m

Deal found 9/19

$421

Thu 9/2411:35 am -

1 stop25h 53m

Sat 9/263:40 pm -

2 stops46h 15m

Deal found 9/20

$423

Thu 10/13:05 pm -

2 stops19h 07m

Mon 10/58:40 pm -

1 stop17h 15m

Deal found 9/22

$404

Tue 10/135:03 pm -

1 stop14h 44m

Thu 11/125:00 am -

1 stop16h 26m

Deal found 9/18

$506

Tue 10/133:05 pm -

1 stop22h 18m

Thu 11/1212:50 pm -

1 stop21h 45m

Deal found 9/18

$523

One-way flights from Kingston to Chicago
Search for one-way flight options from Kingston to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.

Mon 10/123:05 pm -

1 stop22h 18m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/19

$251

Thu 11/54:00 pm -

1 stop26h 43m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/19

$261

Thu 10/83:05 pm -

2 stops53h 07m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/22

$266

Fri 10/163:05 pm -

1 stop17h 55m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/18

$283

Thu 11/510:01 am -

3 stops37h 42m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/19

$312

Sun 11/297:55 pm -

1 stop16h 45m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/20

$408

Fri 11/612:45 pm -

3 stops27h 52m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/19

$428

Sun 12/206:35 am -

1 stop10h 04m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/18

$440

Find flight deals from Kingston to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$444 (Travelocity)
One-way from	$251 (Trip.com)
Popular in	April
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. 26% potential increase in price ($211 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Mon 10/12

3:05 pm-1:23 pm

1 stop22h 18m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$251

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Fri 10/16

3:05 pm-9:00 am

1 stop17h 55m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$283

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Thu 11/5

10:01 am-10:43 pm

3 stops37h 42m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$312

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Thu 11/12

4:00 pm-8:48 pm

1 stop29h 48m

Chicago O'Hare Intl

Thu 11/26

8:40 pm-11:35 am

1 stop13h 55m

$447

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Fri 10/16

3:05 pm-7:07 pm

3 stops28h 02m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$452

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Thu 11/12

7:08 am-4:12 pm

2 stops10h 04m

Chicago O'Hare Intl

Thu 11/26

7:00 am-7:42 pm

2 stops11h 42m

$454

Quickest round-trip

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Sun 10/11

9:15 am-8:38 pm

1 stop11h 23m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$466

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Thu 11/5

2:58 pm-12:11 am

1 stop10h 13m

Chicago O'Hare Intl

Thu 11/12

2:13 pm-1:52 pm

1 stop22h 39m

$478

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Tue 10/13

5:03 pm-7:47 am

1 stop14h 44m

Chicago O'Hare Intl

Thu 11/12

5:00 am-10:26 pm

1 stop16h 26m

$506

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Tue 10/13

3:05 pm-1:23 pm

1 stop22h 18m

Chicago O'Hare Intl

Thu 11/12

12:50 pm-11:35 am

1 stop21h 45m

$523

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/19

Showing 1-10 of 17 resultsSorted by cheapest first

Compare providers for flights from Kingston to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Kingston to Chicago in September.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust 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.

KIN-CHI

KIN-ORD

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

KIN-CHI

KIN-ORD

No data available for this route at this time. Please check back soon.

Related info for your journey

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?
Air Canada, Copa Airlines, and American Airlines can get you from Kingston to Chicago in just under 10h 13m. Your travel time can differ by up to 13h 39m. 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 $400. Another airline that can offer you cheap pricing is JetBlue. American Airlines is priced at 30% 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 American Airlines. According to our data, you can fly for as low as $259. Users have also found prices from $266 and $268 on JetBlue 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.

See more FAQs

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Valparaiso

Hammond

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Porter

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Montego Bay to O'Hare Intl flights

Kingston to O'Hare Intl flights

Top 2 airlines flying from Kingston to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$400	Average$757	FlexibilityNo cancel fee	On-time71%
JetBlue	Cheapest$446	Average$589	FlexibilityNo cancel fee	On-time62%

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$251+ Cheap flights from Kingston (KIN) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Kingston to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Kingston to Chicago

Cheapest flights from Kingston to ChicagoExplore 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 September 22, 2026.

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 September 22, 2026.

Best flights from Kingston to ChicagoDiscover carefully curated flight deals from Kingston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.

Discover carefully curated flight deals from Kingston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.

Last-minute flights from Kingston to ChicagoDiscover last-minute flight deals from Kingston to Chicago. Data last updated September 22, 2026 and is based on user searches.

Discover last-minute flight deals from Kingston to Chicago. Data last updated September 22, 2026 and is based on user searches.

One-way flights from Kingston to ChicagoSearch for one-way flight options from Kingston to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.

Search for one-way flight options from Kingston to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.

Find flight deals from Kingston to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Cheapflights Fare Finder

Use the filters below to find and compare flights from Kingston to Chicago that are best for you.

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 September.

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.

Cheapflights Insights

Related info for your journey

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

How long is the flight from Kingston to Chicago?

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

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

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

How can I find direct flights from Kingston to Chicago?

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

Traveling to a place near Chicago?

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.

Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.

Complete your trip

Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Kingston to Chicago by cabin class

Find flights from Kingston to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Kingston and Chicago flights

Browse other Kingston and Chicago flight options. Last updated on September 22, 2026.

Other flights from Kingston

Browse through other flights departing from Kingston. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Top 2 airlines flying from Kingston to Chicago

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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 September 22, 2026.

Best flights from Kingston to Chicago
Discover carefully curated flight deals from Kingston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.

Last-minute flights from Kingston to Chicago
Discover last-minute flight deals from Kingston to Chicago. Data last updated September 22, 2026 and is based on user searches.

One-way flights from Kingston to Chicago
Search for one-way flight options from Kingston to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.