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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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$360
(Expedia)

One-way from

$203
(Cheapflightsfares)

Popular in

July

Cheapest in

October

Average price

$585
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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Highest demand for flights based on searches. 30% potential increase in price ($253 potential increase over avg. RT price).
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Cheapest flight prices on average. 20% potential price decrease ($99 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 2/261:26 pmKIN - ORD
1 stop9h 37mSpirit Airlines
Wed 3/55:10 amORD - KIN
1 stop7h 18mSpirit Airlines
Deal found 2/19$346
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 3/125:00 amKIN - ORD
2 stops9h 24mAmerican Airlines
Sun 3/168:05 amORD - KIN
2 stops11h 30mAmerican Airlines
Deal found 2/18$404
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Wed 3/121:36 pmKIN - ORD
2 stops18h 08mMultiple Airlines
Sun 3/165:55 amORD - KIN
3 stops38h 40mMultiple Airlines
Deal found 2/18$512
This JetBlue deal was found by Cheapflights users on 2/19. 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.
Fri 7/189:09 amKIN - ORD
1 stop14h 16mJetBlue
Tue 7/2211:35 amORD - KIN
1 stop12h 18mJetBlue
Deal found 2/19$560
This Air Canada deal was found by Cheapflights users on 2/19. 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.
Fri 7/183:05 pmKIN - ORD
2 stops18h 49mAir Canada
Tue 7/225:55 pmORD - KIN
1 stop20h 10mAir Canada
Deal found 2/19$663

Find flights from Kingston to Chicago within your budget

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 February 20, 2025.

Fly from

Kingston

Fly to

Chicago

Route

Depart

Return

Price

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 4/5

1:36 pm-8:44 am

2 stops19h 08m

Chicago O'Hare Intl

Sat 4/12

7:49 pm-12:31 pm

1 stop16h 42m

$360

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 3/12

5:00 am-2:24 pm

2 stops9h 24m

Chicago O'Hare Intl

Sun 3/16

8:05 am-7:35 pm

2 stops11h 30m

$404

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 3/12

1:36 pm-7:44 am

2 stops18h 08m

Chicago O'Hare Intl

Sun 3/16

5:55 am-8:35 pm

3 stops38h 40m

$512

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 7/18

9:09 am-11:25 pm

1 stop14h 16m

Chicago O'Hare Intl

Tue 7/22

11:35 am-11:53 pm

1 stop12h 18m

$560

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 7/18

3:05 pm-9:54 am

2 stops18h 49m

Chicago O'Hare Intl

Tue 7/22

5:55 pm-2:05 pm

1 stop20h 10m

$663

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 4/16

1:39 pm-12:41 am

1 stop11h 02m

$203

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 4/15

2:47 am-12:27 pm

1 stop9h 40m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
OneTravelPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kingston-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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.

Travel insights for flights from Kingston to Chicago

Get recent, data-driven insights about flights from Kingston to Chicago including ideal travel times, pricing trends, and more.

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

Currently, August is the cheapest month in which you can book a flight from Kingston to Chicago (average of $245). Flying from Kingston to Chicago in March is currently the most expensive (average of $321). 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 February 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kingston to Chicago as you normally would.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 20, 2025.
See what other customers who have flown with JetBlue, American Airlines and Air Canada from Kingston to Chicago have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.4
Good
3,070 reviews

Boarding

7.6

Entertainment

7.3

Comfort

7.7

Crew

8.1

Food

6.8

Overall

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

JetBlue
7.4
Good
3,070 reviews
JetBlue
7.4
Good
3,070 reviews

Boarding

7.6

Entertainment

7.3

Comfort

7.7

Crew

8.1

Food

6.8

Overall

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

American Airlines
7.2
Good
10,000 reviews
JetBlue
7.4
Good
3,070 reviews

Boarding

7.6

Entertainment

7.3

Comfort

7.7

Crew

8.1

Food

6.8

Overall

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

Air Canada
7.0
Good
8,748 reviews
JetBlue
7.4
Good
3,070 reviews

Boarding

7.6

Entertainment

7.3

Comfort

7.7

Crew

8.1

Food

6.8

Overall

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

Spirit Airlines
6.3
Okay
8,013 reviews
JetBlue
7.4
Good
3,070 reviews

Boarding

7.6

Entertainment

7.3

Comfort

7.7

Crew

8.1

Food

6.8

Overall

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

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. 3 airlines have flights to Chicago from Kingston Norman Manley on a regular basis.

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

    Cheapflights users have booked flights from Kingston to Chicago round-trip from $360. Other airlines that can offer you cheap pricing are American Airlines, from $404, and JetBlue, from $560. Spirit Airlines is priced at 38% 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, August is the cheapest month in which you can book a flight from Kingston to Chicago (average of $245). Flying from Kingston to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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
Montego Bay to Midway flights
Kingston to O'Hare Intl flights

Top 3 airlines flying from Kingston to Chicago

Discover the top 3 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$290Average$402FlexibilityNo cancel feeOn-time65%
DeltaCheapest$322Average$415FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$402Average$602FlexibilityNo cancel feeOn-time71%
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