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Kingston

$166+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Jul 29 — Aug 51
Wed 7/29
Wed 8/5
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 June 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am
ORD
-
KIN
1 stop6h 09m
JetBlue
Fri 9/253:05 pm
KIN
-
ORD
1 stop8h 26m
JetBlue
Deal found 6/28$390
This American Airlines deal was found by Cheapflights users on 6/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am
ORD
-
KIN
1 stop10h 02m
American Airlines
Thu 9/171:08 pm
KIN
-
ORD
1 stop10h 24m
American Airlines
Deal found 6/24$398
This Cheapflightsfares deal was found by Cheapflights users on 6/27. 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.
Sun 9/206:00 am
ORD
-
KIN
1 stop6h 09m
JetBlue
Thu 9/241:50 pm
KIN
-
ORD
1 stop9h 41m
JetBlue
Deal found 6/27$417
This JetBlue deal was found by Cheapflights users on 6/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:35 pm
ORD
-
KIN
1 stop9h 06m
JetBlue
Thu 9/173:05 pm
KIN
-
ORD
1 stop8h 26m
JetBlue
Deal found 6/24$418
This Cheapflightsfares deal was found by Cheapflights users on 6/24. 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.
Tue 9/17:00 am
ORD
-
KIN
1 stop10h 18m
JetBlue
Wed 9/233:05 pm
KIN
-
ORD
1 stop8h 26m
JetBlue
Deal found 6/24$437
This American Airlines deal was found by Cheapflights users on 6/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:37 am
ORD
-
KIN
1 stop8h 05m
American Airlines
Sat 8/292:00 pm
KIN
-
ORD
1 stop8h 31m
American Airlines
Deal found 6/24$438
This JetBlue deal was found by Cheapflights users on 6/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am
ORD
-
KIN
1 stop10h 18m
JetBlue
Fri 9/183:05 pm
KIN
-
ORD
1 stop8h 26m
JetBlue
Deal found 6/24$441
This American Airlines deal was found by Cheapflights users on 6/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORD
-
KIN
1 stop10h 42m
American Airlines
Sun 8/236:05 am
KIN
-
ORD
1 stop17h 25m
American Airlines
Deal found 6/24$443
This JetBlue deal was found by Cheapflights users on 6/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:35 pm
ORD
-
KIN
1 stop9h 06m
JetBlue
Sat 9/193:05 pm
KIN
-
ORD
1 stop8h 26m
JetBlue
Deal found 6/24$445
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:00 am
ORD
-
KIN
2 stops11h 03m
American Airlines
Sun 7/196:20 am
KIN
-
ORD
1 stop18h 06m
American Airlines
Deal found 6/26$458
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:46 pm
MDW
-
KIN
1 stop7h 27m
Delta
Sun 8/239:13 am
KIN
-
MDW
1 stop7h 02m
Delta
Deal found 6/25$464
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:29 am
MDW
-
KIN
2 stops10h 41m
Delta
Fri 9/259:10 am
KIN
-
MDW
1 stop7h 06m
Delta
Deal found 6/28$469

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 June 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$390
(Cheapflightsfares)

One-way from

$166
(Cheapflightsfares)

Popular in

November

Cheapest in

August

Average price

$795
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. 5% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 29, 2026.
Use the filters below to find and compare flights from Chicago to Kingston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 8/24

2:35 pm-11:41 pm

1 stop9h 06m

Kingston Norman Manley

Wed 8/26

12:08 pm-11:44 pm

1 stop11h 36m

$438

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 9/22

10:48 am-8:10 pm

1 stop9h 22m

Kingston Norman Manley

Fri 9/25

9:10 am-10:45 pm

1 stop13h 35m

$464

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 7/16

6:35 am-8:04 pm

1 stop13h 29m

Kingston Norman Manley

Sat 7/25

9:00 am-5:12 pm

1 stop8h 12m

$476
Quickest round-trip

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 7/1

9:30 am-7:53 pm

2 stops10h 23m

Kingston Norman Manley

Tue 7/7

5:03 pm-12:26 am

1 stop7h 23m

$506

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 7/3

3:21 pm-1:54 pm

1 stop22h 33m

Kingston Norman Manley

Sun 7/5

2:56 pm-1:57 pm

1 stop23h 01m

$525

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 7/18

5:00 am-3:55 pm

2 stops10h 55m

Kingston Norman Manley

Tue 7/21

5:03 pm-12:26 am

1 stop7h 23m

$528

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 8/16

7:09 am-4:24 pm

2 stops9h 15m

Kingston Norman Manley

Tue 8/25

5:16 pm-9:00 am

2 stops15h 44m

$528

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 8/16

7:00 am-5:18 pm

1 stop10h 18m

Kingston Norman Manley

Wed 8/19

12:08 pm-11:44 pm

1 stop11h 36m

$538

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 7/7

5:00 am-8:12 pm

2 stops15h 12m

Kingston Norman Manley

Thu 7/9

12:40 pm-12:26 am

1 stop11h 46m

$539

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 9/4

6:05 am-8:13 pm

1 stop14h 08m

Kingston Norman Manley

Sun 9/13

9:10 am-10:45 pm

1 stop13h 35m

$550

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 33 resultsSorted by cheapest first
1
2
3
4

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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Kingston flight deals on Cheapflights vs. FlightHub >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 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 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, December is the cheapest month in which you can book a flight from Chicago to Kingston (average of $84). Flying from Chicago to Kingston in July is currently the most expensive (average of $471). 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.

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 80% 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.

Miami (MIA) is the most affordable 1-stop option, with an average round-trip price of $670.

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 Miami (MIA) have the shortest average one-way travel time for 1-stop routes: 7h 04m.

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 24m.

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 June 29, 2026.
Read through reviews of airlines operating flights from Chicago to Kingston, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,766 reviews

Crew

7.9

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,766 reviews
American Airlines
7.1
Good
11,766 reviews

Crew

7.9

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 2 different airlines.

  • How long is the flight from Chicago to Kingston?

    A quick flight from Chicago to Kingston can take about 9h 06m. JetBlue provides one of the quickest options available for as low as $438. Chicago and Kingston are separated by a distance of 1785 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?

    American Airlines, at $433, was found to be the cheapest airline from Chicago to Kingston. An alternate airline flying to your destination would be Delta. Users have found that American Airlines is 34% 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, December is the cheapest month in which you can book a flight from Chicago to Kingston (average of $84). Flying from Chicago to Kingston in July is currently the most expensive (average of $471). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Chicago to Kingston

Discover the top 2 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 June 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$433Average$660FlexibilityNo cancel feeOn-time71%
DeltaCheapest$445Average$646FlexibilityNo cancel feeOn-timeN/A

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