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$203+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$346
(oojo)

One-way from

$203
(Mytrip)

Popular in

April

Cheapest in

March

Average price

$460
Provider with most accurate pricing for Kingston Norman Manley-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Kingston Norman Manley-Chicago (CHI) flights.
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From Kingston Norman Manley to Chicago (CHI)
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One-way flight from Kingston Norman Manley to Chicago (CHI)
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:19 pmKIN - ORD
2 stops34h 26mMultiple Airlines
Fri 1/27:30 amORD - KIN
1 stop27h 44mMultiple Airlines
Deal found 11/11$371
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:19 pmKIN - ORD
1 stop12h 11mSpirit Airlines
Fri 1/25:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Deal found 11/11$380
This oojo deal was found by Cheapflights users on 11/12. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/271:19 pmKIN - ORD
1 stop12h 11mSpirit Airlines
Sat 1/35:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Deal found 11/12$397
This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/252:24 pmKIN - ORD
1 stop7h 03mSpirit Airlines
Thu 11/275:00 amORD - KIN
1 stop7h 21mSpirit Airlines
Deal found 11/12$421
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/214:30 pmKIN - ORD
2 stops30h 27mMultiple Airlines
Wed 12/33:43 pmORD - KIN
1 stop19h 31mMultiple Airlines
Deal found 11/11$442
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:19 pmKIN - ORD
1 stop12h 11mSpirit Airlines
Sat 12/279:09 pmORD - KIN
2 stops14h 05mSpirit Airlines
Deal found 11/10$452
This Mytrip deal was found by Cheapflights users on 11/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/254:30 pmKIN - ORD
2 stops19h 48mMultiple Airlines
Thu 11/275:00 amORD - KIN
1 stop7h 21mMultiple Airlines
Deal found 11/12$478
This Expedia deal was found by Cheapflights users on 11/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:30 pmKIN - ORD
1 stop28h 22mJetBlue
Sat 3/76:04 amORD - KIN
1 stop12h 50mJetBlue
Deal found 11/12$485
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Thu 12/181:19 pmKIN - ORD
1 stop12h 11mMultiple Airlines
Mon 12/2212:39 pmORD - KIN
2 stops46h 35mMultiple Airlines
Deal found 11/12$513

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 November 13, 2025.
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

Sat 12/27

1:19 pm-12:30 am

1 stop12h 11m

Chicago O'Hare Intl

Sat 1/3

5:00 am-12:14 pm

1 stop6h 14m

$397

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 2/23

1:19 pm-12:18 am

1 stop11h 59m

Chicago O'Hare Intl

Mon 3/2

5:15 am-12:15 pm

1 stop6h 00m

$405

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 3/2

3:47 am-11:48 am

1 stop9h 01m

Chicago O'Hare Intl

Wed 3/4

6:04 am-7:53 pm

1 stop12h 49m

$409

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 3/3

3:00 pm-12:04 am

1 stop10h 04m

Chicago O'Hare Intl

Wed 3/4

7:34 am-1:51 pm

1 stop29h 17m

$445

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 2/23

1:19 pm-12:18 am

1 stop11h 59m

Chicago O'Hare Intl

Mon 3/2

7:25 am-1:45 pm

2 stops29h 20m

$449

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 12/20

1:19 pm-12:30 am

1 stop12h 11m

Chicago O'Hare Intl

Sat 12/27

9:09 pm-12:14 pm

2 stops14h 05m

$452

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 3/3

7:40 am-6:13 pm

2 stops11h 33m

Chicago O'Hare Intl

Wed 3/4

6:47 pm-2:22 pm

2 stops18h 35m

$485

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 12/16

1:19 pm-12:09 am

1 stop11h 50m

$203

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 12/16

1:19 pm-2:31 pm

2 stops26h 12m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Kingston-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, December is the cheapest month in which you can book a flight from Kingston to Chicago (average of $251). Flying from Kingston to Chicago in March is currently the most expensive (average of $477). 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 is the cheapest time of day to fly from KIN to CHI?

Find hourly flight availability from Kingston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Kingston to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 45% on your trip compared to booking a flight in the evening.

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 November 13, 2025.
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
8,007 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Overall

7.9

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
8,007 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Overall

7.9

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
11,051 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Overall

7.9

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 and JetBlue can get you from Kingston to Chicago in just under 9h 01m. Your travel time can differ by up to 3h 10m. 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 $310. Another airline that can offer you cheap pricing is American Airlines. Spirit Airlines is priced at 41% 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, December is the cheapest month in which you can book a flight from Kingston to Chicago (average of $251). Flying from Kingston to Chicago in March is currently the most expensive (average of $477). 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
Hammond
Porter
Benton Harbor
Merrillville

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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
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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$310Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$415Average$536FlexibilityNo cancel feeOn-time71%

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