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$248+ 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 6/18. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$352
(Cheapflightsfares)

One-way from

$248
(Cheapflightsfares)

Popular in

April

Cheapest in

October

Average price

$518
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 June 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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Fri 7/111:37 pmKIN - ORD
1 stop10h 16mSpirit Airlines
Mon 7/145:05 amORD - KIN
1 stop7h 37mSpirit Airlines
Deal found 6/10$352
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:25 pmKIN - ORD
1 stop14h 44mMultiple Airlines
Fri 8/15:40 pmORD - KIN
1 stop14h 07mMultiple Airlines
Deal found 6/10$439
This Orbitz deal was found by Cheapflights users on 6/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/181:45 pmKIN - ORD
2 stops18h 14mAir Canada
Mon 6/232:07 pmORD - KIN
2 stops21h 18mAir Canada
Deal found 6/9$486
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/96:00 amKIN - ORD
1 stop13h 35mAmerican Airlines
Fri 8/226:00 amORD - KIN
1 stop13h 55mAmerican Airlines
Deal found 6/11$518
This JetBlue deal was found by Cheapflights users on 6/10. 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 7/241:10 amKIN - ORD
1 stop10h 09mJetBlue
Fri 8/112:06 pmORD - KIN
1 stop14h 02mJetBlue
Deal found 6/10$543
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/129:00 amKIN - ORD
1 stop9h 49mDelta
Sun 6/157:05 amORD - KIN
2 stops12h 55mDelta
Deal found 6/11$616

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 June 12, 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 7/11

1:37 pm-11:53 pm

1 stop10h 16m

Chicago O'Hare Intl

Mon 7/14

5:05 am-12:42 pm

1 stop7h 37m

$352

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 7/25

6:25 pm-9:09 am

1 stop14h 44m

Chicago O'Hare Intl

Fri 8/1

5:40 pm-7:47 am

1 stop14h 07m

$439

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 7/9

6:00 am-7:35 pm

1 stop13h 35m

Chicago O'Hare Intl

Fri 8/22

6:00 am-7:55 pm

1 stop13h 55m

$518

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 7/24

1:10 am-11:19 am

1 stop10h 09m

Chicago O'Hare Intl

Fri 8/1

12:06 pm-2:08 am

1 stop14h 02m

$543

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/18

1:37 pm-11:45 pm

1 stop10h 08m

$248

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/18

6:00 am-9:10 pm

1 stop15h 10m

$267

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/18

1:45 pm-6:53 pm

2 stops29h 08m

$301

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 6/17

1:06 am-10:13 am

1 stop9h 07m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 12, 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
7.3
Good
2,925 reviews

Food

6.7

Overall

7.3

Comfort

7.6

Entertainment

7.3

Boarding

7.5

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
JetBlue
7.3
Good
2,925 reviews
JetBlue
7.3
Good
2,925 reviews

Food

6.7

Overall

7.3

Comfort

7.6

Entertainment

7.3

Boarding

7.5

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
American Airlines
7.2
Good
10,000 reviews
JetBlue
7.3
Good
2,925 reviews

Food

6.7

Overall

7.3

Comfort

7.6

Entertainment

7.3

Boarding

7.5

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
Air Canada
7.1
Good
9,531 reviews
JetBlue
7.3
Good
2,925 reviews

Food

6.7

Overall

7.3

Comfort

7.6

Entertainment

7.3

Boarding

7.5

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
Spirit Airlines
6.3
Okay
8,052 reviews
JetBlue
7.3
Good
2,925 reviews

Food

6.7

Overall

7.3

Comfort

7.6

Entertainment

7.3

Boarding

7.5

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.

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 $352. Other airlines that can offer you cheap pricing are American Airlines, from $518, and JetBlue, from $543. Spirit Airlines is priced at 29% 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 $248. Users have also found prices from $267 and $301 on American Airlines and Air Canada, 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
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$310Average$406FlexibilityNo cancel feeOn-time65%
DeltaCheapest$322Average$410FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$392Average$597FlexibilityNo cancel feeOn-time71%

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