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$222+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$330
(Delta)

One-way from

$222
(OneTravel)

Popular in

April

Cheapest in

October

Average price

$551
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. 3% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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.
Thu 9/119:00 amKIN - ORD
1 stop14h 54mDelta
Thu 9/187:10 amORD - KIN
2 stops12h 50mDelta
Deal found 7/28$330
This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:55 amKIN - ORD
1 stop9h 44mMultiple Airlines
Thu 9/185:05 amORD - KIN
1 stop15h 00mMultiple Airlines
Deal found 7/28$379
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Thu 9/1812:05 pmORD - KIN
3 stops22h 57mSpirit Airlines
Deal found 7/28$430
This Flighttix deal was found by Cheapflights users on 7/29. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:10 amKIN - ORD
1 stop18h 39mJetBlue
Fri 9/191:35 pmORD - KIN
1 stop11h 09mJetBlue
Deal found 7/29$506

Cheapflights Fare Finder

 
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 July 29, 2025.
Use the filters below to find and compare flights from Kingston to Chicago that are best for you.

Fly from

Kingston

Fly to

Chicago

Route

Depart

Return

Price

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 9/11

9:00 am-11:54 pm

1 stop14h 54m

Chicago O'Hare Intl

Thu 9/18

7:10 am-8:00 pm

2 stops12h 50m

$330

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 9/11

7:55 am-5:39 pm

1 stop9h 44m

Chicago O'Hare Intl

Thu 9/18

5:05 am-8:05 pm

1 stop15h 00m

$379

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 9/11

12:08 pm-10:48 pm

1 stop10h 40m

Chicago O'Hare Intl

Thu 9/18

12:05 pm-11:02 am

3 stops22h 57m

$430

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 9/11

2:10 am-8:49 pm

1 stop18h 39m

Chicago O'Hare Intl

Fri 9/19

1:35 pm-12:44 am

1 stop11h 09m

$506

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 9/15

12:08 pm-10:48 pm

1 stop10h 40m

$222

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 9/14

2:10 am-12:21 pm

1 stop10h 11m

$325

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 8/6

7:55 am-7:04 am

2 stops23h 09m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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.

Cheapflights Insights

Everything you need to know about your flight from Kingston to Chicago

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 July 29, 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.

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 July 29, 2025.
See what other customers who have flown with Delta, JetBlue, and Spirit Airlines from Kingston to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Spirit Airlines
6.3
Okay
8,040 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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 $330. Other airlines that can offer you cheap pricing are Spirit Airlines, from $430, and JetBlue, from $506. Delta is priced at 33% 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$310Average$406FlexibilityNo cancel feeOn-time65%
DeltaCheapest$322Average$411FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$392Average$564FlexibilityNo cancel feeOn-time71%

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