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$228+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$329
(Cheapflightsfares)

One-way from

$280
(OneTravel)

Popular in

April

Cheapest in

March

Average price

$410
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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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($16 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 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 September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/912:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
Thu 1/85:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Deal found 9/14$329
This Mytrip deal was found by Cheapflights users on 9/13. 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 10/1612:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
Mon 10/205:05 amORD - KIN
1 stop6h 04mSpirit Airlines
Deal found 9/13$345
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2712:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Tue 9/306:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Deal found 9/13$352
This Delta deal was found by Cheapflights users on 9/14. 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 10/99:00 amKIN - ORD
1 stop7h 41mDelta
Thu 1/87:00 amORD - KIN
2 stops12h 00mDelta
Deal found 9/14$388
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 10/287:00 amKIN - ORD
1 stop12h 32mAmerican Airlines
Tue 11/47:00 amORD - KIN
1 stop14h 13mAmerican Airlines
Deal found 9/13$397
This Delta deal was found by Cheapflights users on 9/13. 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.
Sat 9/279:00 amKIN - ORD
2 stops12h 34mDelta
Tue 9/307:10 amORD - KIN
2 stops12h 50mDelta
Deal found 9/13$398
This Mytrip deal was found by Cheapflights users on 9/14. 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 10/87:55 amKIN - ORD
1 stop15h 50mMultiple Airlines
Wed 10/157:43 pmORD - KIN
1 stop15h 26mMultiple Airlines
Deal found 9/14$401
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 11/21:14 pmKIN - ORD
1 stop12h 49mSpirit Airlines
Tue 11/47:43 pmORD - KIN
1 stop15h 30mSpirit Airlines
Deal found 9/13$437
This Mytrip deal was found by Cheapflights users on 9/13. 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 10/1612:14 pmKIN - ORD
1 stop11h 31mMultiple Airlines
Mon 10/204:44 pmORD - KIN
2 stops27h 21mMultiple Airlines
Deal found 9/13$457

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 September 15, 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 10/9

12:14 pm-11:45 pm

1 stop11h 31m

Chicago O'Hare Intl

Thu 1/8

5:59 pm-12:13 pm

1 stop17h 14m

$329

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 10/2

12:08 pm-10:48 pm

1 stop10h 40m

Chicago O'Hare Intl

Sun 10/5

5:05 am-11:09 am

1 stop6h 04m

$340

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 10/16

12:14 pm-11:45 pm

1 stop11h 31m

Chicago O'Hare Intl

Mon 10/20

5:05 am-11:09 am

1 stop6h 04m

$345

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 9/27

12:08 pm-11:10 am

2 stops23h 02m

Chicago O'Hare Intl

Tue 9/30

6:44 pm-11:02 am

1 stop16h 18m

$383

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 10/9

9:00 am-4:41 pm

1 stop7h 41m

Chicago O'Hare Intl

Thu 1/8

7:00 am-8:00 pm

2 stops12h 00m

$388

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 10/28

7:00 am-7:32 pm

1 stop12h 32m

Chicago O'Hare Intl

Tue 11/4

7:00 am-10:13 pm

1 stop14h 13m

$397

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 9/27

9:00 am-9:34 pm

2 stops12h 34m

Chicago O'Hare Intl

Tue 9/30

7:10 am-8:00 pm

2 stops12h 50m

$398

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 10/8

7:55 am-11:45 pm

1 stop15h 50m

Chicago O'Hare Intl

Wed 10/15

7:43 pm-11:09 am

1 stop15h 26m

$401

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 10/2

1:45 pm-6:41 pm

2 stops28h 56m

Chicago O'Hare Intl

Sun 10/5

2:08 pm-12:35 pm

2 stops46h 27m

$416

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 10/3

12:08 pm-10:48 pm

1 stop10h 40m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 15 results
1
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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 September 15, 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 September 15, 2025.
See what other customers who have flown with Delta and American 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
7,956 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,956 reviews
Delta
8.0
Very good
7,956 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,956 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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.

  • How long is the flight from Kingston to Chicago?

    Spirit Airlines can get you from Kingston to Chicago in just under 11h 31m. Your travel time can differ by up to . There are 1785 mi between Kingston and Chicago.

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

    Cheapflights users have booked flights from Kingston to Chicago round-trip from $310. Other airlines that can offer you cheap pricing are Delta, from $322, and American Airlines, from $402. Spirit Airlines is priced at 41% lower than the current average price of a flight leaving 3 months from now.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $228. Users have also found prices from $269 and $356 on American Airlines and JetBlue, respectively.

  • 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
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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
Kingston to O'Hare Intl flights
Montego Bay to Midway 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$310Average$406FlexibilityNo cancel feeOn-time65%
DeltaCheapest$322Average$588FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$402Average$543FlexibilityNo cancel feeOn-time71%

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