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$221+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Apr 30 — May 71
Wed 4/30
Wed 5/7
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 April 25, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$329
(American Airlines)

One-way from

$221
(Spirit)

Popular in

April

Cheapest in

October

Average price

$697
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. 4% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 25, 2025.

This American Airlines deal was found by Cheapflights users on 4/24. 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 5/96:30 amKIN - ORD
1 stop12h 51mAmerican Airlines
Sun 5/111:41 pmORD - KIN
1 stop5h 59mAmerican Airlines
Deal found 4/24$329
This Cheapflightsfares deal was found by Cheapflights users on 4/24. 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.
Fri 5/161:34 pmKIN - ORD
1 stop10h 31mSpirit Airlines
Mon 5/197:35 pmORD - KIN
1 stop16h 54mSpirit Airlines
Deal found 4/24$343
This Delta deal was found by Cheapflights users on 4/25. 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.
Sun 5/119:00 amKIN - ORD
1 stop6h 48mDelta
Wed 9/1011:19 amORD - KIN
1 stop8h 36mDelta
Deal found 4/25$361
This JetBlue deal was found by Cheapflights users on 4/23. 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 6/131:06 amKIN - ORD
1 stop9h 07mJetBlue
Sun 6/156:15 amORD - KIN
1 stop15h 14mJetBlue
Deal found 4/23$803

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 April 25, 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

Fri 5/9

6:30 am-7:21 pm

1 stop12h 51m

Chicago O'Hare Intl

Sun 5/11

1:41 pm-7:40 pm

1 stop5h 59m

$329

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/16

1:34 pm-12:05 am

1 stop10h 31m

Chicago O'Hare Intl

Mon 5/19

7:35 pm-12:29 pm

1 stop16h 54m

$343

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 5/11

9:00 am-3:48 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 9/10

11:19 am-7:55 pm

1 stop8h 36m

$361

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 6/13

1:06 am-10:13 am

1 stop9h 07m

Chicago O'Hare Intl

Sun 6/15

6:15 am-9:29 pm

1 stop15h 14m

$803

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 5/8

1:34 pm-12:05 am

1 stop10h 31m

$221

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 6/15

9:00 am-6:49 pm

1 stop9h 49m

$252

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 7/22

6:00 am-3:52 pm

2 stops9h 52m

$261

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 7/21

1:04 am-10:47 am

1 stop9h 43m

$293

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 5/8

1:34 pm-2:15 pm

3 stops24h 41m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

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

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 April 25, 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 April 25, 2025.
See what other customers who have flown with Delta, JetBlue and American Airlines 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.
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
JetBlue
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Spirit Airlines
6.3
Okay
7,943 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 $329. Other airlines that can offer you cheap pricing are Spirit Airlines, from $343, and Delta, from $361. American Airlines is priced at 31% 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 $221. Users have also found prices from $252 and $261 on Delta and American Airlines, 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 Kingston?

Book flights to Kingston if you plan to visit one of these locations
Merrillville
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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$310Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$322Average$411FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$402Average$602FlexibilityNo cancel feeOn-time71%

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