HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kingston

$135+ Cheap flights from Chicago (CHI) to Kingston (KIN)

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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Kingston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Kingston

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kingston (KIN). 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 30, 2025.

Round-trip from

$335
(Cheapflightsfares)

One-way from

$135
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$550
From Chicago (CHI) to Kingston Norman Manley
Search Deals
One-way flight from Chicago (CHI) to Kingston Norman Manley
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($114 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Chicago to Kingston

Cheapest flights from Chicago to Kingston
Explore the most affordable flight options available from Chicago to Kingston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Wed 10/112:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Deal found 7/29$335
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 9/116:00 amMDW - KIN
1 stop14h 00mDelta
Thu 9/189:00 amKIN - MDW
1 stop12h 36mDelta
Deal found 7/28$375
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:30 amORD - KIN
1 stop14h 30mDelta
Sat 9/279:00 amKIN - ORD
1 stop10h 05mDelta
Deal found 7/29$375
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/289:15 amMDW - KIN
3 stops31h 55mMultiple Airlines
Wed 9/36:25 pmKIN - MDW
2 stops18h 38mMultiple Airlines
Deal found 7/29$827

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Kingston 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 30, 2025.
Use the filters below to find and compare flights from Chicago to Kingston that are best for you.

Fly from

Chicago

Fly to

Kingston

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 9/16

6:44 pm-11:02 am

1 stop16h 18m

Kingston Norman Manley

Wed 10/1

12:08 pm-10:48 pm

1 stop10h 40m

$335

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 9/11

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Thu 9/18

9:00 am-9:36 pm

1 stop12h 36m

$375

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 9/18

5:30 am-8:00 pm

1 stop14h 30m

Kingston Norman Manley

Mon 9/22

9:00 am-9:25 pm

1 stop12h 25m

$375

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 9/25

8:10 am-7:38 pm

2 stops11h 28m

Kingston Norman Manley

Fri 10/3

1:00 pm-11:48 pm

2 stops10h 48m

$443

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 8/28

9:15 am-5:10 pm

3 stops31h 55m

Kingston Norman Manley

Wed 9/3

6:25 pm-1:03 pm

2 stops18h 38m

$827

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 8/19

5:05 am-11:27 am

1 stop6h 22m

$135

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 8/19

12:43 pm-8:25 pm

1 stop7h 42m

$212

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 8/19

9:16 am-11:27 am

2 stops26h 11m

$237

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 8/18

6:15 am-6:09 pm

1 stop11h 54m

$497

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 8/14

1:07 am-4:55 pm

3 stops15h 48m

$736

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Best time to book a flight from Chicago to Kingston

Have a flexible travel schedule? Discover the best time to fly to Kingston from Chicago 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 Chicago to Kingston

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Kingston (average of $425). Flying from Chicago to Kingston in December is currently the most expensive (average of $613). 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 CHI to KIN?

Find hourly flight availability from Chicago to Kingston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Kingston in the evening. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight in the afternoon.

Reviews of airlines servicing Kingston

Get insights into the airlines that provide service to Kingston. 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 Kingston. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Chicago to Kingston, such as Delta, JetBlue, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,048 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kingston. 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 into for flights to Kingston from Chicago?

    Located just 5.1 mi from the city center, Kingston Norman Manley is the airport most travelers will use when flying to Kingston from Chicago. Booking flights from Chicago to Norman Manley (KIN) should be relatively easy as there are 0 daily inbound flights from Chicago from 3 different airlines.

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

    Spirit Airlines, at $335, was found to be the cheapest airline from Chicago to Kingston. An alternate airline flying to your destination would be Delta. Users have found that Spirit Airlines is 40% cheaper than the other options available to this destination.

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

    $135 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and JetBlue, with prices starting from $401 and $497, respectively.

  • Can I find deals for flights from Chicago to Kingston that include hotel bookings?

    Yes. In addition to deals on Chicago to Kingston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kingston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kingston.

  • Can I find deals for business class flights from Chicago to Kingston?

    Yes. Cheapflights offers flight deals from Chicago to Kingston 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 Chicago to Kingston?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Kingston (average of $425). Flying from Chicago to Kingston in December is currently the most expensive (average of $613). 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
Port Antonio

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 3 airlines flying from Chicago to Kingston

Discover the top 3 airlines that operate flights from Chicago to Kingston. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$295Average$860FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$307Average$379FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$450Average$626FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.