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Kingston

$141+ Cheap flights from Chicago (CHI) to Kingston (KIN)

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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Chicago to Kingston

Cheapest flights from Chicago to Kingston
Explore the most affordable flight options available from Chicago to Kingston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This CheapOair deal was found by Cheapflights users on 12/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:30 pmORD - KIN
1 stop16h 15mMultiple Airlines
Fri 1/95:01 amKIN - ORD
2 stops13h 42mMultiple Airlines
Deal found 12/28$699
This CheapOair deal was found by Cheapflights users on 12/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:01 pmORD - KIN
2 stops22h 44mMultiple Airlines
Mon 1/51:04 pmKIN - ORD
2 stops21h 52mMultiple Airlines
Deal found 12/26$762
This FlightHub deal was found by Cheapflights users on 12/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:30 pmORD - KIN
1 stop16h 15mAir Canada
Fri 1/92:55 pmKIN - ORD
1 stop23h 06mAir Canada
Deal found 12/26$774
This Air Canada deal was found by Cheapflights users on 12/28. 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.
Tue 12/306:16 pmORD - KIN
1 stop18h 29mAir Canada
Wed 1/72:55 pmKIN - ORD
1 stop29h 50mAir Canada
Deal found 12/28$776
This WestJet deal was found by Cheapflights users on 12/26. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/289:29 amMDW - KIN
2 stops29h 04mWestJet
Tue 1/64:30 pmKIN - MDW
2 stops17h 22mWestJet
Deal found 12/26$3,907

Find flight deals from Chicago to Kingston

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kingston (KIN). 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$347
(Kiwi.com)

One-way from

$141
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$758
Provider with most accurate pricing for Chicago (CHI)-Kingston Norman Manley flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kingston Norman Manley flights.
Search Deals
From Chicago (CHI) to Kingston Norman Manley
Search Deals
One-way flight from Chicago (CHI) to Kingston Norman Manley
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($198 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Kingston 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 December 28, 2025.
Use the filters below to find and compare flights from Chicago to Kingston that are best for you.

Fly from

Chicago

Fly to

Kingston

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 1/29

2:52 pm-12:12 pm

1 stop20h 20m

Kingston Norman Manley

Mon 2/2

1:17 pm-11:22 am

1 stop23h 05m

$363

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 1/17

5:32 pm-12:12 pm

1 stop17h 40m

Kingston Norman Manley

Fri 1/23

1:17 pm-9:03 pm

1 stop8h 46m

$388

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 2/26

8:16 pm-12:15 pm

1 stop14h 59m

Kingston Norman Manley

Sun 3/1

1:17 pm-9:11 am

2 stops20h 54m

$422

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 1/23

5:15 am-12:12 pm

1 stop5h 57m

Kingston Norman Manley

Sun 1/25

1:17 pm-11:46 pm

1 stop11h 29m

$430

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 1/27

11:51 pm-1:53 pm

1 stop13h 02m

Kingston Norman Manley

Thu 2/5

3:00 pm-12:04 am

1 stop10h 04m

$433

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 1/20

11:51 pm-1:53 pm

1 stop13h 02m

Kingston Norman Manley

Wed 1/28

3:00 pm-12:24 am

1 stop10h 24m

$433

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 1/19

10:46 am-8:00 pm

1 stop8h 14m

Kingston Norman Manley

Sat 1/24

9:00 am-3:38 pm

1 stop7h 38m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 1/22

10:48 am-8:00 pm

1 stop8h 12m

Kingston Norman Manley

Sat 1/24

9:00 am-3:38 pm

1 stop7h 38m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 3/13

6:25 am-8:00 pm

1 stop13h 35m

Kingston Norman Manley

Thu 3/19

9:00 am-4:55 pm

1 stop7h 55m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 3/13

6:25 am-8:00 pm

1 stop13h 35m

Kingston Norman Manley

Tue 3/17

9:00 am-10:31 pm

1 stop13h 31m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

Showing 1-10 of 38 results
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Compare providers for flights from Chicago to Kingston

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 Chicago to Kingston in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapTicketsDealPrice 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 Chicago-Kingston flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Kingston flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Kingston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Kingston 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 Chicago-Kingston 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 Chicago to Kingston

Have a flexible travel schedule? Discover the best time to fly to Kingston from Chicago 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 Chicago to Kingston

What is the cheapest month to book a flight from Chicago to Kingston?

Currently, January is the cheapest month in which you can book a flight from Chicago to Kingston (average of $193). Flying from Chicago to Kingston in March is currently the most expensive (average of $408). 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 CHI to KIN?

Find hourly flight availability from Chicago to Kingston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 28, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Kingston in the evening. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight at noon.

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

What’s the top layover airport for flights from Chicago to Kingston?

Share of 1-stop round-trip flights from Chicago to Kingston chosen by Cheapflights users in the past 12 months, using the same layover each way.

Miami (MIA) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Kingston on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Kingston?

Average round-trip fare for 1-stop flights from Chicago to Kingston, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $359.

What’s the fastest layover option from Chicago to Kingston?

Shortest average travel time for 1-stop one-way flights from Chicago to Kingston, 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: 5h 57m.

Which airport typically offers the quickest layover for flights from Chicago to Kingston?

Average layover duration for 1-stop one-way flights from Chicago to Kingston, 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 2h 54m.

Reviews of airlines servicing Kingston

Get insights into the airlines that provide service to Kingston. 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 Kingston. Reviews last updated December 28, 2025.
Read through reviews of airlines operating flights from Chicago to Kingston, such as Delta, American Airlines, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,013 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Comfort

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
8,013 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Comfort

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
11,071 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Comfort

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.
Spirit Airlines
6.3
Okay
8,221 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Comfort

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 Chicago to Kingston. 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 into for flights to Kingston from Chicago?

    Located just 5.1 mi from the city center, Kingston Norman Manley is the airport most travelers will use when flying to Kingston from Chicago. Booking flights from Chicago to Norman Manley (KIN) should be relatively easy as there are 0 daily inbound flights from Chicago from 3 different airlines.

  • How long is the flight from Chicago to Kingston?

    A quick flight from Chicago to Kingston can take about 8h 14m. Spirit Airlines provides one of the quickest options available for as low as $445. Chicago and Kingston are separated by a distance of 1769 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Spirit Airlines, at $304, was found to be the cheapest airline from Chicago to Kingston.Alternate airlines to your destination round-trip include Delta and American Airlines. Users have found that Spirit Airlines is 46% cheaper than the other options available to this destination.

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

    Yes. In addition to deals on Chicago to Kingston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kingston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kingston.

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

    Yes. Cheapflights offers flight deals from Chicago to Kingston 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 Chicago to Kingston?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Kingston (average of $193). Flying from Chicago to Kingston in March is currently the most expensive (average of $408). 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 Kingston?

Book flights to Kingston if you plan to visit one of these locations
Port Antonio

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Top 3 airlines flying from Chicago to Kingston

Discover the top 3 airlines that operate flights from Chicago to Kingston. 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$304Average$398FlexibilityNo cancel feeOn-time65%
DeltaCheapest$369Average$706FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$433Average$613FlexibilityNo cancel feeOn-time71%

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