$303+ Cheap flights from Chicago (CHI) to Kingston (KIN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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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
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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
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Cheapest flights from Chicago to KingstonExplore 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 November 10, 2026.
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 November 10, 2026.
This Copa Airlines deal was found by Cheapflights users on 11/5. 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 11/182:13 pm -
1 stop22h 39m
Sun 11/222:58 pm -
1 stop10h 13m
Deal found 11/5![Copa Airlines logo]()
$546
This Copa Airlines deal was found by Cheapflights users on 11/9. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:13 pm -
1 stop22h 39m
Sun 11/152:58 pm -
1 stop22h 48m
Deal found 11/9![Copa Airlines logo]()
$566
This Copa Airlines deal was found by Cheapflights users on 11/9. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:17 pm -
1 stop22h 33m
Mon 12/143:03 pm -
1 stop10h 08m
Deal found 11/9![Copa Airlines logo]()
$616
This Copa Airlines deal was found by Cheapflights users on 11/6. 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.
Sun 12/62:17 pm -
1 stop22h 33m
Sun 12/133:03 pm -
1 stop10h 08m
Deal found 11/6![Copa Airlines logo]()
$676
This Copa Airlines deal was found by Cheapflights users on 11/5. 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.
Fri 12/42:17 pm -
1 stop22h 33m
Tue 12/153:03 pm -
1 stop10h 08m
Deal found 11/5![Copa Airlines logo]()
$728
This Copa Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 12/102:17 pm -
1 stop22h 33m
Wed 2/33:05 pm -
1 stop10h 06m
Deal found 11/5![Copa Airlines logo]()
$757
This Booking.com deal was found by Cheapflights users on 11/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:35 am -
3 stops30h 40m
Sun 12/137:55 pm -
1 stop14h 13m
Deal found 11/8![Multiple Airlines logo]()
$787
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Tue 12/12:59 pm -
1 stop7h 48m
Thu 12/173:41 pm -
1 stop8h 52m
Deal found 11/5![JetBlue logo]()
$804
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Sun 12/62:59 pm -
1 stop7h 48m
Fri 12/181:15 pm -
1 stop11h 18m
Deal found 11/5![JetBlue logo]()
$806
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Wed 12/22:59 pm -
1 stop7h 48m
Wed 12/166:01 am -
1 stop8h 29m
Deal found 11/5![JetBlue logo]()
$807
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Tue 12/12:59 pm -
1 stop7h 48m
Tue 12/151:18 pm -
1 stop11h 15m
Deal found 11/5![JetBlue logo]()
$808
This JetBlue deal was found by Cheapflights users on 11/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:59 pm -
1 stop7h 48m
Thu 12/173:41 pm -
1 stop8h 52m
Deal found 11/9![JetBlue logo]()
$809
Best flights from Chicago to KingstonDiscover carefully curated flight deals from Chicago to Kingston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 10, 2026.
Discover carefully curated flight deals from Chicago to Kingston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 10, 2026.
This Copa Airlines deal was found by Cheapflights users on 11/5. 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.
Mon 1/182:13 pm -
1 stop22h 40m
Thu 1/213:01 pm -
1 stop10h 06m
Deal found 11/5![Copa Airlines logo]()
$587
This United Airlines deal was found by Cheapflights users on 11/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:00 am -
2 stops31h 52m
Sun 11/222:58 pm -
1 stop10h 13m
Deal found 11/8![United Airlines logo]()
$897
This Copa Airlines deal was found by Cheapflights users on 11/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/282:13 pm -
1 stop22h 40m
Sun 1/313:01 pm -
1 stop10h 10m
Deal found 11/7![Copa Airlines logo]()
$587
This Copa Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 1/212:13 pm -
1 stop22h 40m
Mon 1/253:01 pm -
1 stop10h 06m
Deal found 11/6![Copa Airlines logo]()
$587
This Copa Airlines deal was found by Cheapflights users on 11/5. 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 1/202:13 pm -
1 stop22h 40m
Sat 1/233:01 pm -
1 stop22h 45m
Deal found 11/5![Copa Airlines logo]()
$607
This Copa Airlines deal was found by Cheapflights users on 11/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:17 pm -
1 stop22h 33m
Mon 12/143:03 pm -
1 stop10h 08m
Deal found 11/7![Copa Airlines logo]()
$616
This United Airlines deal was found by Cheapflights users on 11/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
2 stops30h 52m
Sun 11/152:58 pm -
1 stop22h 48m
Deal found 11/7![United Airlines logo]()
$897
This Copa Airlines deal was found by Cheapflights users on 11/8. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/62:17 pm -
1 stop22h 33m
Sun 12/133:03 pm -
1 stop10h 08m
Deal found 11/8![Copa Airlines logo]()
$676
This Copa Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 12/102:17 pm -
1 stop22h 33m
Wed 2/33:05 pm -
1 stop10h 06m
Deal found 11/5![Copa Airlines logo]()
$757
This Copa Airlines deal was found by Cheapflights users on 11/6. 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 1/92:13 pm -
1 stop22h 40m
Sat 1/233:01 pm -
1 stop22h 45m
Deal found 11/6![Copa Airlines logo]()
$789
Last-minute flights from Chicago to KingstonDiscover last-minute flight deals from Chicago to Kingston. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kingston. Data last updated November 10, 2026 and is based on user searches.
This Copa Airlines deal was found by Cheapflights users on 11/9. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:13 pm -
1 stop22h 39m
Sun 11/152:58 pm -
1 stop22h 48m
Deal found 11/9![Copa Airlines logo]()
$566
This Copa Airlines deal was found by Cheapflights users on 11/5. 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 11/182:13 pm -
1 stop22h 39m
Sun 11/222:58 pm -
1 stop10h 13m
Deal found 11/5![Copa Airlines logo]()
$546
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Tue 12/12:59 pm -
1 stop7h 48m
Thu 12/173:41 pm -
1 stop8h 52m
Deal found 11/5![JetBlue logo]()
$804
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Tue 12/12:59 pm -
1 stop7h 48m
Tue 12/151:18 pm -
1 stop11h 15m
Deal found 11/5![JetBlue logo]()
$808
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Wed 12/22:59 pm -
1 stop7h 48m
Sat 12/121:18 pm -
1 stop11h 15m
Deal found 11/5![JetBlue logo]()
$807
This Copa Airlines deal was found by Cheapflights users on 11/5. 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.
Fri 12/42:17 pm -
1 stop22h 33m
Tue 12/153:03 pm -
1 stop10h 08m
Deal found 11/5![Copa Airlines logo]()
$728
This Copa Airlines deal was found by Cheapflights users on 11/6. 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.
Sun 12/62:17 pm -
1 stop22h 33m
Sun 12/133:03 pm -
1 stop10h 08m
Deal found 11/6![Copa Airlines logo]()
$676
This Booking.com deal was found by Cheapflights users on 11/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:35 am -
3 stops30h 40m
Sun 12/137:55 pm -
1 stop14h 13m
Deal found 11/8![Multiple Airlines logo]()
$787
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Sun 12/62:59 pm -
1 stop7h 48m
Fri 12/181:15 pm -
1 stop11h 18m
Deal found 11/5![JetBlue logo]()
$806
This Copa Airlines deal was found by Cheapflights users on 11/9. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:17 pm -
1 stop22h 33m
Mon 12/143:03 pm -
1 stop10h 08m
Deal found 11/9![Copa Airlines logo]()
$616
This JetBlue deal was found by Cheapflights users on 11/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:59 pm -
1 stop7h 48m
Sat 12/121:18 pm -
1 stop11h 15m
Deal found 11/9![JetBlue logo]()
$809
This Copa Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 12/102:17 pm -
1 stop22h 33m
Wed 2/33:05 pm -
1 stop10h 06m
Deal found 11/5![Copa Airlines logo]()
$757
One-way flights from Chicago to KingstonSearch for one-way flight options from Chicago to Kingston. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
Search for one-way flight options from Chicago to Kingston. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 11/1610:19 am -
3 stops26h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$303
This American Airlines deal was found by Cheapflights users on 11/6. 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 1/152:38 pm -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![American Airlines logo]()
$353
This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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.
Sat 1/307:00 am -
1 stop5h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![JetBlue logo]()
$362
This JetBlue deal was found by Cheapflights users on 11/5. 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.
Sun 1/32:47 pm -
1 stop8h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![JetBlue logo]()
$367
This American Airlines deal was found by Cheapflights users on 11/7. 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 1/3010:36 am -
2 stops10h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![American Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 1/159:48 pm -
3 stops20h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 11/5. 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 1/39:33 pm -
2 stops11h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$385
This United Airlines deal was found by Cheapflights users on 11/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:13 pm -
1 stop22h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![United Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 1/34:18 pm -
3 stops19h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$503
Find 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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $587 (Copa Airlines) |
One-way from | $303 (Kiwi.com) |
Popular in | February |
Cheapest in | September |
Average price | $884 |
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 7,457,451 searches. Data last updated November 10, 2026.
Use the filters below to find and compare flights from Chicago to Kingston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Fri 1/15
9:56 am-10:32 pm
2 stops11h 36m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$353
Quickest round-trip
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sun 1/3
2:47 pm-12:45 am
1 stop8h 58m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$367
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sat 1/30
10:36 am-10:32 pm
2 stops10h 56m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$379
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 11/16
2:13 pm-1:52 pm
1 stop22h 39m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$404
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 1/18
2:13 pm-1:53 pm
1 stop22h 40m
Kingston Norman Manley
Thu 1/21
3:01 pm-12:07 am
1 stop10h 06m
$587
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Thu 1/28
2:13 pm-1:53 pm
1 stop22h 40m
Kingston Norman Manley
Sun 1/31
3:01 pm-12:11 am
1 stop10h 10m
$587
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Thu 1/21
2:13 pm-1:53 pm
1 stop22h 40m
Kingston Norman Manley
Mon 1/25
3:01 pm-12:07 am
1 stop10h 06m
$587
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Wed 1/20
2:13 pm-1:53 pm
1 stop22h 40m
Kingston Norman Manley
Sat 1/23
3:01 pm-12:46 pm
1 stop22h 45m
$607
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 12/7
2:17 pm-1:50 pm
1 stop22h 33m
Kingston Norman Manley
Mon 12/14
3:03 pm-12:11 am
1 stop10h 08m
$616
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sun 12/6
2:17 pm-1:50 pm
1 stop22h 33m
Kingston Norman Manley
Sun 12/13
3:03 pm-12:11 am
1 stop10h 08m
$676
Showing 1-10 of 14 resultsSorted by cheapest first
Compare providers for flights from Chicago to Kingston
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 Chicago to Kingston in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Kingston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Kingston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Kingston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Kingston 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 Chicago-Kingston 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 Chicago to Kingston
Have a flexible travel schedule? Discover the best time to fly to Kingston from Chicago with our price prediction graph.
CHI-KIN
ORD-KIN
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
CHI-KIN
ORD-KIN
What is the cheapest month to book a flight from Chicago to Kingston?
Currently, August is the cheapest month in which you can book a flight from Chicago to Kingston (average of $513). Flying from Chicago to Kingston in November is currently the most expensive (average of $894). 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.
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 November 10, 2026.
Read through reviews of airlines operating flights from Chicago to Kingston, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
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.
Traveling to a place near Kingston?
Book flights to Kingston if you plan to visit one of these locationsPort 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.
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Alternative routes for Chicago to Kingston
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kingston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Kingston by cabin class
Find flights from Chicago to Kingston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Kingston
Explore flights to Kingston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 10, 2026.
Chicago and Kingston flights
Browse other Chicago and Kingston flight options. Last updated on November 10, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on November 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Kingston
Discover the top 2 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 7,457,451 searches. Data last updated November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$438 | Average$677 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$445 | Average$638 | FlexibilityNo cancel fee | On-timeN/A |