$261+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
KIN — CHI
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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Find cheap flights from Kingston to Chicago 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 Kingston to Chicago
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Best
Last-minute
One-way
Cheapest flights from Kingston to ChicagoExplore 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 August 13, 2026.
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 August 13, 2026.
This Travelocity deal was found by Cheapflights users on 8/9. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:45 pm -
1 stop29h 58m
Tue 12/84:30 pm -
1 stop18h 05m
Deal found 8/9![Air Canada logo]()
$417
This Travelocity deal was found by Cheapflights users on 8/11. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:45 pm -
1 stop29h 58m
Sun 12/63:45 pm -
2 stops42h 50m
Deal found 8/11![Air Canada logo]()
$429
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 9/253:05 pm -
1 stop8h 03m
Fri 10/26:00 am -
1 stop6h 45m
Deal found 8/10![JetBlue logo]()
$447
This Air Canada deal was found by Cheapflights users on 8/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:45 pm -
1 stop21h 23m
Mon 12/76:40 pm -
1 stop15h 55m
Deal found 8/11![Air Canada logo]()
$450
This Orbitz deal was found by Cheapflights users on 8/9. 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 10/143:05 pm -
1 stop22h 18m
Thu 10/228:45 am -
2 stops29h 10m
Deal found 8/9![Air Canada logo]()
$456
This Copa Airlines deal was found by Cheapflights users on 8/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:57 pm -
1 stop10h 05m
Sat 9/263:20 pm -
1 stop22h 31m
Deal found 8/10![Copa Airlines logo]()
$484
This Cheapflightsfares deal was found by Cheapflights users on 8/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:55 pm -
1 stop7h 49m
Mon 11/167:00 am -
1 stop5h 45m
Deal found 8/9![JetBlue logo]()
$493
This Expedia deal was found by Cheapflights users on 8/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:05 pm -
1 stop17h 55m
Mon 10/58:40 pm -
1 stop17h 15m
Deal found 8/8![Air Canada logo]()
$502
Best flights from Kingston to ChicagoDiscover carefully curated flight deals from Kingston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Kingston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 9/253:05 pm -
1 stop8h 03m
Fri 10/26:00 am -
1 stop6h 45m
Deal found 8/10![JetBlue logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 8/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:57 pm -
1 stop10h 05m
Sat 9/263:20 pm -
1 stop22h 31m
Deal found 8/10![Copa Airlines logo]()
$484
This Orbitz deal was found by Cheapflights users on 8/8. 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 9/303:05 pm -
1 stop17h 55m
Mon 10/58:40 pm -
1 stop17h 15m
Deal found 8/8![Air Canada logo]()
$502
This American Airlines deal was found by Cheapflights users on 8/8. 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.
Sat 8/296:05 am -
1 stop16h 26m
Sat 9/195:00 am -
1 stop11h 02m
Deal found 8/8![American Airlines logo]()
$520
This Copa Airlines deal was found by Cheapflights users on 8/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:57 pm -
1 stop10h 05m
Mon 10/53:20 pm -
1 stop22h 38m
Deal found 8/12![Copa Airlines logo]()
$504
This American Airlines deal was found by Cheapflights users on 8/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:09 pm -
1 stop10h 21m
Sat 10/310:05 am -
1 stop5h 57m
Deal found 8/10![American Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 8/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:09 pm -
2 stops10h 47m
Sat 9/266:30 am -
2 stops9h 32m
Deal found 8/10![American Airlines logo]()
$524
Last-minute flights from Kingston to ChicagoDiscover last-minute flight deals from Kingston to Chicago. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Kingston to Chicago. Data last updated August 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/8. 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.
Sat 8/292:00 pm -
1 stop10h 35m
Mon 9/216:59 am -
1 stop9h 03m
Deal found 8/8![American Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:57 pm -
1 stop10h 05m
Tue 9/88:01 am -
1 stop29h 50m
Deal found 8/10![Copa Airlines logo]()
$514
This Orbitz deal was found by Cheapflights users on 8/7. 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.
Sat 9/51:55 pm -
1 stop9h 49m
Sun 9/138:40 pm -
1 stop17h 15m
Deal found 8/7![Multiple Airlines logo]()
$519
This Air Canada deal was found by Cheapflights users on 8/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:05 pm -
2 stops19h 10m
Wed 9/165:35 pm -
1 stop16h 50m
Deal found 8/12![Air Canada logo]()
$523
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/91:09 pm -
1 stop10h 21m
Wed 9/1610:05 am -
1 stop5h 57m
Deal found 8/12![American Airlines logo]()
$525
This Copa Airlines deal was found by Cheapflights users on 8/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:57 pm -
1 stop10h 05m
Sat 9/263:20 pm -
1 stop22h 31m
Deal found 8/10![Copa Airlines logo]()
$484
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 9/253:05 pm -
1 stop8h 03m
Fri 10/26:00 am -
1 stop6h 45m
Deal found 8/10![JetBlue logo]()
$447
This Expedia deal was found by Cheapflights users on 8/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:05 pm -
1 stop17h 55m
Mon 10/58:40 pm -
1 stop17h 15m
Deal found 8/8![Air Canada logo]()
$502
This Copa Airlines deal was found by Cheapflights users on 8/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:57 pm -
1 stop10h 05m
Mon 10/53:20 pm -
1 stop22h 38m
Deal found 8/12![Copa Airlines logo]()
$504
One-way flights from Kingston to ChicagoSearch for one-way flight options from Kingston to Chicago. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Kingston to Chicago. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Orbitz deal was found by Cheapflights users on 8/8. 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 10/2811:45 am -
1 stop29h 58m
Deal found 8/8![Air Canada logo]()
$261
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 9/42:15 am -
1 stop14h 03m
Deal found 8/7![JetBlue logo]()
$298
This Expedia deal was found by Cheapflights users on 8/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:05 pm -
1 stop25h 53m
Deal found 8/12![Air Canada logo]()
$320
This American Airlines deal was found by Cheapflights users on 8/7. 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.
Sat 9/56:05 am -
2 stops12h 49m
Deal found 8/7![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 8/8. 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.
Sun 9/271:09 pm -
1 stop10h 21m
Deal found 8/8![American Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Tue 9/1510:03 am -
3 stops32h 20m
Deal found 8/12![Multiple Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Sun 9/278:35 pm -
3 stops39h 16m
Deal found 8/8![Multiple Airlines logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:45 pm -
3 stops48h 14m
Deal found 8/9![Multiple Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 8/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:42 pm -
1 stop17h 12m
Deal found 8/9![American Airlines logo]()
$451
Find 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 August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $417 (Travelocity) |
One-way from | $261 (Orbitz) |
Popular in | April |
Cheapest in | January |
Average price | $449 |
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 August 13, 2026.
Use the filters below to find and compare flights from Kingston to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Fri 9/25
3:05 pm-11:08 pm
1 stop8h 03m
Chicago O'Hare Intl
Fri 10/2
6:00 am-12:45 pm
1 stop6h 45m
$447
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Sat 9/19
2:57 pm-1:02 am
1 stop10h 05m
Chicago O'Hare Intl
Sat 9/26
3:20 pm-1:51 pm
1 stop22h 31m
$484
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Wed 9/30
3:05 pm-9:00 am
1 stop17h 55m
Chicago O'Hare Intl
Mon 10/5
8:40 pm-1:55 pm
1 stop17h 15m
$502
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Wed 9/30
2:57 pm-1:02 am
1 stop10h 05m
Chicago O'Hare Intl
Mon 10/5
3:20 pm-1:58 pm
1 stop22h 38m
$504
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Sat 8/29
6:05 am-10:31 pm
1 stop16h 26m
Chicago O'Hare Intl
Sat 9/19
5:00 am-4:02 pm
1 stop11h 02m
$520
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Thu 10/1
1:09 pm-11:30 pm
1 stop10h 21m
Chicago O'Hare Intl
Sat 10/3
10:05 am-4:02 pm
1 stop5h 57m
$520
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Sat 9/19
1:09 pm-11:56 pm
2 stops10h 47m
Chicago O'Hare Intl
Sat 9/26
6:30 am-4:02 pm
2 stops9h 32m
$524
Cheapest one-way
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Wed 10/28
11:45 am-2:52 pm
2 stops27h 07m
$265
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Fri 9/4
2:15 am-4:18 pm
1 stop14h 03m
$298
KingstonChicago
KIN Kingston Norman Manley - ORD Chicago O'Hare Intl
KINORD
Kingston Norman Manley
Sun 9/27
1:09 pm-11:30 pm
1 stop10h 21m
$332
Showing 1-10 of 18 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Kingston-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kingston-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.
KIN-CHI
KIN-ORD
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
KIN-CHI
KIN-ORD
No data available for this route at this time. Please check back soon.
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 13, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Kingston to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kingston and Chicago flights
Browse other Kingston and Chicago flight options. Last updated on August 13, 2026.
Other flights from Kingston
Browse through other flights departing from Kingston. Flights are based on user searches made on Cheapflights and were last updated on August 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Kingston to Chicago
Discover the top airline 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 August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$446 | Average$589 | FlexibilityNo cancel fee | On-time62% |