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Kingston

$196+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
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 May 11, 2026.

This Super.com deal was found by Cheapflights users on 5/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:00 am
ORD
-
KIN
1 stop5h 43m
JetBlue
Mon 10/124:05 pm
KIN
-
ORD
1 stop7h 39m
JetBlue
Deal found 5/10$424
This JetBlue deal was found by Cheapflights users on 5/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:00 am
ORD
-
KIN
1 stop10h 06m
JetBlue
Wed 8/196:00 am
KIN
-
ORD
1 stop7h 39m
JetBlue
Deal found 5/10$446
This Super.com deal was found by Cheapflights users on 5/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 am
ORD
-
KIN
1 stop5h 43m
JetBlue
Sat 9/264:05 pm
KIN
-
ORD
1 stop7h 39m
JetBlue
Deal found 5/9$454
This Cheapflightsfares deal was found by Cheapflights users on 5/10. 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 10/87:00 am
ORD
-
KIN
1 stop5h 43m
JetBlue
Mon 10/124:05 pm
KIN
-
ORD
1 stop7h 39m
JetBlue
Deal found 5/10$469
This JetBlue deal was found by Cheapflights users on 5/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:00 am
ORD
-
KIN
1 stop10h 06m
JetBlue
Fri 8/141:56 pm
KIN
-
ORD
1 stop9h 48m
JetBlue
Deal found 5/10$474
This Super.com deal was found by Cheapflights users on 5/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:00 am
ORD
-
KIN
1 stop5h 46m
JetBlue
Fri 9/111:53 pm
KIN
-
ORD
1 stop9h 51m
JetBlue
Deal found 5/9$493
This Cheapflightsfares deal was found by Cheapflights users on 5/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:00 am
ORD
-
KIN
1 stop10h 06m
JetBlue
Sun 9/134:05 pm
KIN
-
ORD
1 stop7h 39m
JetBlue
Deal found 5/11$497
This JetBlue deal was found by Cheapflights users on 5/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:35 pm
ORD
-
KIN
1 stop6h 45m
JetBlue
Fri 8/141:56 pm
KIN
-
ORD
1 stop9h 48m
JetBlue
Deal found 5/10$502
This FlightHub deal was found by Cheapflights users on 5/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:35 pm
ORD
-
KIN
1 stop6h 45m
Multiple Airlines
Tue 7/283:05 pm
KIN
-
ORD
1 stop17h 55m
Multiple Airlines
Deal found 5/10$511
This JetBlue deal was found by Cheapflights users on 5/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:00 am
ORD
-
KIN
1 stop10h 06m
JetBlue
Mon 8/176:00 am
KIN
-
ORD
1 stop7h 39m
JetBlue
Deal found 5/10$512
This Copa Airlines deal was found by Cheapflights users on 5/8. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:20 am
ORD
-
KIN
1 stop12h 34m
Copa Airlines
Tue 7/282:56 pm
KIN
-
ORD
1 stop13h 04m
Copa Airlines
Deal found 5/8$516
This Priceline deal was found by Cheapflights users on 5/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:51 pm
ORD
-
KIN
2 stops24h 04m
Multiple Airlines
Mon 10/124:05 pm
KIN
-
ORD
1 stop7h 39m
Multiple Airlines
Deal found 5/10$518

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 May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$424
(Super.com)

One-way from

$196
(Super.com)

Popular in

November

Cheapest in

August

Average price

$572
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. 10% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 11, 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 8/3

7:00 am-5:06 pm

1 stop10h 06m

Kingston Norman Manley

Fri 8/14

1:56 pm-11:44 pm

1 stop9h 48m

$474
Quickest round-trip

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 8/8

2:35 pm-9:20 pm

1 stop6h 45m

Kingston Norman Manley

Thu 8/13

6:00 am-1:39 pm

1 stop7h 39m

$502

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 7/21

1:20 am-1:54 pm

1 stop12h 34m

Kingston Norman Manley

Tue 7/28

2:56 pm-4:00 am

1 stop13h 04m

$516

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 8/7

7:00 am-5:06 pm

1 stop10h 06m

Kingston Norman Manley

Tue 8/18

6:00 am-1:39 pm

1 stop7h 39m

$580

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 9/19

9:30 am-7:30 pm

2 stops10h 00m

Kingston Norman Manley

Sat 9/26

9:00 am-6:31 pm

2 stops9h 31m

$581

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 5/29

8:00 am-4:08 pm

2 stops8h 08m

Kingston Norman Manley

Wed 6/3

7:50 am-11:00 pm

1 stop15h 10m

$581

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 6/1

5:30 am-8:00 pm

1 stop14h 30m

Kingston Norman Manley

Thu 6/4

9:00 am-1:01 pm

2 stops28h 01m

$581

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 7/22

10:41 am-10:25 am

2 stops23h 44m

Kingston Norman Manley

Tue 7/28

3:05 pm-10:16 am

2 stops19h 11m

$624

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 6/21

1:00 am-1:54 pm

1 stop12h 54m

Kingston Norman Manley

Sun 7/5

2:56 pm-4:00 am

1 stop13h 04m

$635

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 6/6

10:45 am-8:00 pm

1 stop9h 15m

Kingston Norman Manley

Sat 6/13

9:00 am-10:17 pm

1 stop13h 17m

$660

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 38 resultsSorted by cheapest first
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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 May.
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 April is currently the most expensive (average of $556). 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 67% 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 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 May 11, 2026.
Read through reviews of airlines operating flights from Chicago to Kingston, such as American Airlines and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,664 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.1

Comfort

7.2

Food

6.4

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,664 reviews
American Airlines
7.1
Good
11,664 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.1

Comfort

7.2

Food

6.4

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
Spirit Airlines
6.3
Okay
8,634 reviews
American Airlines
7.1
Good
11,664 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.1

Comfort

7.2

Food

6.4

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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 10h. JetBlue provides one of the quickest options available for as low as $581. 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 $100, was found to be the cheapest airline from Chicago to Kingston. An alternate airline flying to your destination would be American Airlines. Users have found that Spirit Airlines is 84% 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 April is currently the most expensive (average of $556). 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 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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$534FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$433Average$633FlexibilityNo cancel feeOn-time71%

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