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Kingston

$139+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$334
(Cheapflightsfares)

One-way from

$139
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$414
From Chicago (CHI) to Kingston Norman Manley
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One-way flight from Chicago (CHI) to Kingston Norman Manley
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Highest demand for flights based on searches. 17% potential increase in price ($120 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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 11/145:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Mon 11/171:28 pmKIN - ORD
1 stop11h 14mSpirit Airlines
Deal found 9/8$334
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Mon 11/175:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Mon 12/81:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/10$342
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 11/115:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Wed 12/31:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/9$344
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 11/65:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Tue 11/111:28 pmKIN - ORD
1 stop11h 14mSpirit Airlines
Deal found 9/10$347
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 10/116:00 pmORD - KIN
2 stops17h 09mSpirit Airlines
Sun 10/1912:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
Deal found 9/9$364
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/187:43 pmORD - KIN
1 stop15h 26mSpirit Airlines
Sun 10/2612:14 pmKIN - ORD
1 stop22h 36mSpirit Airlines
Deal found 9/9$366
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/236:18 pmORD - KIN
2 stops16h 51mSpirit Airlines
Mon 10/2712:14 pmKIN - ORD
1 stop12h 49mSpirit Airlines
Deal found 9/10$369
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 9/245:46 pmORD - KIN
2 stops17h 16mSpirit Airlines
Fri 10/312:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Deal found 9/9$371
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/25:46 pmORD - KIN
2 stops17h 16mSpirit Airlines
Thu 10/912:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
Deal found 9/10$373
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amMDW - KIN
1 stop13h 00mDelta
Mon 12/89:00 amKIN - MDW
1 stop8h 36mDelta
Deal found 9/10$433
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:35 amMDW - KIN
1 stop9h 25mDelta
Wed 10/159:00 amKIN - MDW
1 stop7h 09mDelta
Deal found 9/11$517
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:35 amMDW - KIN
2 stops10h 25mDelta
Wed 10/89:00 amKIN - MDW
2 stops9h 25mDelta
Deal found 9/10$522

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 September 11, 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

Fri 11/14

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Mon 11/17

1:28 pm-11:42 pm

1 stop11h 14m

$334

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 11/6

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Tue 11/11

1:28 pm-11:42 pm

1 stop11h 14m

$347

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/11

6:00 pm-11:09 am

2 stops17h 09m

Kingston Norman Manley

Sun 10/19

12:14 pm-11:45 pm

1 stop11h 31m

$364

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/25

6:00 pm-11:09 am

2 stops17h 09m

Kingston Norman Manley

Mon 10/27

12:14 pm-1:03 am

1 stop12h 49m

$371

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 9/24

6:44 pm-11:02 am

1 stop16h 18m

Kingston Norman Manley

Fri 10/3

12:08 pm-10:48 pm

1 stop10h 40m

$376

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 11/10

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Thu 12/4

1:28 pm-9:00 pm

1 stop8h 32m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 11/8

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Fri 12/5

1:28 pm-9:00 pm

1 stop8h 32m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 11/14

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Fri 12/5

1:28 pm-9:00 pm

1 stop8h 32m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/18

6:00 pm-11:09 am

2 stops17h 09m

Kingston Norman Manley

Sun 10/26

12:14 pm-10:50 am

1 stop22h 36m

$395

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 9/19

5:46 pm-11:02 am

2 stops17h 16m

Kingston Norman Manley

Mon 9/22

12:08 pm-10:48 pm

1 stop10h 40m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 22 results
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2
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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, September is the cheapest month in which you can book a flight from Chicago to Kingston (average of $425). Flying from Chicago to Kingston in December is currently the most expensive (average of $613). 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 September 11, 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 44% on your trip compared to booking a flight in the afternoon.

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.

Fort Lauderdale (FLL) – 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 Fort Lauderdale (FLL) offer the fastest connection on this route, with an average layover time of 3h 16m.

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 September 11, 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
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 13h. Spirit Airlines provides one of the quickest options available for as low as $433. 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?

    Delta, at $295, was found to be the cheapest airline from Chicago to Kingston.Alternate airlines to your destination round-trip include Spirit Airlines and American Airlines. Users have found that Delta is 47% cheaper than the other options available to this destination.

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

    $139 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $178 and $178, respectively.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Kingston (average of $425). Flying from Chicago to Kingston in December is currently the most expensive (average of $613). 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

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.

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$295Average$784FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$310Average$395FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$450Average$610FlexibilityNo cancel feeOn-time71%

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