$177+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Kingston with Cheapflights
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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 September 24, 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 September 24, 2026.
This Expedia deal was found by Cheapflights users on 9/22. 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 9/238:40 pm -
1 stop13h 45m
Tue 9/293:05 pm -
1 stop23h 50m
Deal found 9/22![Air Canada logo]()
$448
This Air Canada deal was found by Cheapflights users on 9/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:18 pm -
1 stop13h 07m
Fri 10/23:05 pm -
2 stops19h 07m
Deal found 9/23![Air Canada logo]()
$456
This Trip.com deal was found by Cheapflights users on 9/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:00 pm -
1 stop23h 55m
Mon 10/53:05 pm -
1 stop23h 50m
Deal found 9/20![Air Canada logo]()
$460
This Air Canada deal was found by Cheapflights users on 9/20. 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 9/238:40 pm -
1 stop13h 45m
Thu 10/13:05 pm -
1 stop20h 16m
Deal found 9/20![Air Canada logo]()
$463
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:59 am -
1 stop9h 16m
Fri 10/309:15 am -
1 stop6h 59m
Deal found 9/23![Delta logo]()
$494
This Mytrip deal was found by Cheapflights users on 9/22. 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.
Tue 10/206:21 am -
2 stops31h 34m
Tue 10/2711:45 am -
2 stops30h 02m
Deal found 9/22![Multiple Airlines logo]()
$789
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 12/46:00 am -
1 stop13h 00m
Mon 12/79:00 am -
1 stop8h 16m
Deal found 9/21![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 10/2710:59 am -
1 stop9h 16m
Sat 11/79:15 am -
2 stops9h 45m
Deal found 9/21![Delta logo]()
$849
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:04 am -
1 stop14h 11m
Mon 10/269:15 am -
1 stop6h 59m
Deal found 9/23![Delta logo]()
$854
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:29 am -
2 stops10h 46m
Sat 10/179:15 am -
1 stop13h 18m
Deal found 9/23![Delta logo]()
$859
This Mytrip deal was found by Cheapflights users on 9/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
3 stops30h 55m
Fri 10/3011:45 am -
2 stops30h 02m
Deal found 9/23![Multiple Airlines logo]()
$864
This Mytrip deal was found by Cheapflights users on 9/22. 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 10/226:22 am -
3 stops25h 48m
Mon 10/269:10 am -
3 stops32h 17m
Deal found 9/22![Multiple Airlines logo]()
$870
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 September 24, 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 September 24, 2026.
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:21 am -
1 stop8h 54m
Fri 10/309:15 am -
1 stop7h 43m
Deal found 9/23![Delta logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 9/22. 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 11/52:13 pm -
1 stop22h 39m
Thu 11/122:58 pm -
1 stop10h 13m
Deal found 9/22![Copa Airlines logo]()
$536
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 11/77:00 am -
1 stop5h 48m
Fri 11/132:58 pm -
1 stop9h 57m
Deal found 9/18![JetBlue logo]()
$596
This American Airlines deal was found by Cheapflights users on 9/18. 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 11/79:50 am -
2 stops11h 36m
Fri 11/137:08 am -
1 stop13h 41m
Deal found 9/18![American Airlines logo]()
$642
This Mytrip deal was found by Cheapflights users on 9/19. 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.
Mon 10/126:00 am -
3 stops31h 55m
Fri 10/163:05 pm -
3 stops33h 24m
Deal found 9/19![Multiple Airlines logo]()
$834
This United Airlines deal was found by Cheapflights users on 9/20. 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 11/302:13 pm -
1 stop22h 37m
Sun 12/63:03 pm -
1 stop10h 08m
Deal found 9/20![United Airlines logo]()
$842
This Copa Airlines deal was found by Cheapflights users on 9/22. 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 11/62:13 pm -
1 stop22h 39m
Fri 11/132:58 pm -
1 stop10h 13m
Deal found 9/22![Copa Airlines logo]()
$556
This JetBlue deal was found by Cheapflights users on 9/20. 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 11/297:00 am -
1 stop8h 00m
Tue 12/86:01 am -
1 stop8h 29m
Deal found 9/20![JetBlue logo]()
$792
This Copa Airlines deal was found by Cheapflights users on 9/22. 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 10/163:20 pm -
1 stop22h 35m
Mon 10/192:57 pm -
1 stop10h 00m
Deal found 9/22![Copa Airlines logo]()
$758
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 12/46:00 am -
1 stop13h 00m
Mon 12/79:00 am -
1 stop8h 16m
Deal found 9/21![Delta logo]()
$844
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Tue 12/12:13 pm -
1 stop22h 37m
Sat 12/123:03 pm -
2 stops19h 34m
Deal found 9/20![United Airlines logo]()
$852
This JetBlue deal was found by Cheapflights users on 9/20. 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 11/297:00 am -
1 stop8h 00m
Mon 12/73:41 pm -
1 stop8h 52m
Deal found 9/20![JetBlue logo]()
$838
This Delta deal was found by Cheapflights users on 9/19. 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.
Mon 10/126:04 am -
1 stop14h 11m
Fri 10/169:15 am -
1 stop13h 18m
Deal found 9/19![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/20. 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 12/36:00 am -
1 stop13h 00m
Tue 12/89:00 am -
1 stop8h 16m
Deal found 9/20![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 10/1912:49 pm -
1 stop7h 26m
Mon 10/269:15 am -
1 stop13h 18m
Deal found 9/21![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/20. 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.
Tue 12/11:02 pm -
1 stop5h 58m
Wed 12/99:00 am -
1 stop8h 16m
Deal found 9/20![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/20. 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.
Tue 12/11:02 pm -
1 stop5h 58m
Sun 12/69:00 am -
1 stop14h 54m
Deal found 9/20![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 11/711:33 am -
1 stop7h 42m
Fri 11/139:00 am -
1 stop8h 18m
Deal found 9/18![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/21. 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 11/56:04 am -
1 stop13h 11m
Thu 11/129:00 am -
2 stops10h 04m
Deal found 9/21![Delta logo]()
$849
This Delta deal was found by Cheapflights users on 9/22. 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 10/229:29 am -
2 stops10h 46m
Mon 10/269:15 am -
1 stop13h 18m
Deal found 9/22![Delta logo]()
$849
This Delta deal was found by Cheapflights users on 9/22. 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.
Wed 10/76:04 am -
1 stop14h 11m
Sat 10/179:15 am -
1 stop13h 18m
Deal found 9/22![Delta logo]()
$907
This Delta deal was found by Cheapflights users on 9/20. 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.
Mon 11/3011:27 am -
1 stop7h 33m
Thu 12/109:00 am -
1 stop8h 16m
Deal found 9/20![Delta logo]()
$907
Last-minute flights from Chicago to KingstonDiscover last-minute flight deals from Chicago to Kingston. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kingston. Data last updated September 24, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 9/22. 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 9/238:40 pm -
1 stop13h 45m
Tue 9/293:05 pm -
1 stop23h 50m
Deal found 9/22![Air Canada logo]()
$448
This Air Canada deal was found by Cheapflights users on 9/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:18 pm -
1 stop13h 07m
Fri 10/23:05 pm -
2 stops19h 07m
Deal found 9/23![Air Canada logo]()
$456
This Air Canada deal was found by Cheapflights users on 9/20. 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 9/238:40 pm -
1 stop13h 45m
Thu 10/13:05 pm -
1 stop20h 16m
Deal found 9/20![Air Canada logo]()
$463
This Trip.com deal was found by Cheapflights users on 9/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:00 pm -
1 stop23h 55m
Mon 10/53:05 pm -
1 stop23h 50m
Deal found 9/20![Air Canada logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Thu 9/2411:45 am -
1 stop26h 45m
Mon 10/56:25 pm -
1 stop16h 35m
Deal found 9/20![Multiple Airlines logo]()
$880
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:29 am -
2 stops10h 46m
Sat 10/179:15 am -
1 stop13h 18m
Deal found 9/23![Delta logo]()
$859
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 10/1912:49 pm -
1 stop7h 26m
Mon 10/269:15 am -
1 stop13h 18m
Deal found 9/21![Delta logo]()
$844
This Mytrip deal was found by Cheapflights users on 9/22. 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.
Tue 10/206:21 am -
2 stops31h 34m
Tue 10/2711:45 am -
2 stops30h 02m
Deal found 9/22![Multiple Airlines logo]()
$789
This Mytrip deal was found by Cheapflights users on 9/22. 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 10/226:22 am -
3 stops25h 48m
Mon 10/269:10 am -
3 stops32h 17m
Deal found 9/22![Multiple Airlines logo]()
$870
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:59 am -
1 stop9h 16m
Fri 10/309:15 am -
1 stop6h 59m
Deal found 9/23![Delta logo]()
$494
This Mytrip deal was found by Cheapflights users on 9/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
3 stops30h 55m
Fri 10/3011:45 am -
2 stops30h 02m
Deal found 9/23![Multiple Airlines logo]()
$864
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 10/2710:59 am -
1 stop9h 16m
Sat 11/79:15 am -
2 stops9h 45m
Deal found 9/21![Delta logo]()
$849
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 September 24, 2026.
Search for one-way flight options from Chicago to Kingston. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Trip.com deal was found by Cheapflights users on 9/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:15 pm -
1 stop23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Air Canada logo]()
$177
This Orbitz deal was found by Cheapflights users on 9/19. 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.
Thu 10/86:21 pm -
2 stops19h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Air Canada logo]()
$192
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Tue 11/179:50 am -
2 stops11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$198
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:30 am -
1 stop12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$202
This Orbitz deal was found by Cheapflights users on 9/22. 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.
Mon 11/24:30 pm -
1 stop18h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Air Canada logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/67:11 am -
3 stops30h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$296
This Mytrip deal was found by Cheapflights users on 9/19. 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.
Tue 10/66:25 am -
2 stops31h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/116:00 am -
3 stops55h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/116:24 am -
3 stops31h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 9/19. 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.
Tue 10/612:49 pm -
1 stop7h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Delta logo]()
$377
This Mytrip deal was found by Cheapflights users on 9/19. 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 10/81:12 pm -
2 stops24h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 12/2211:36 am -
3 stops30h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$514
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 September 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $472 (Air Canada) |
One-way from | $177 (Trip.com) |
Popular in | February |
Cheapest in | September |
Average price | $473 |
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 September 24, 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
Tue 10/6
2:15 pm-1:55 pm
1 stop23h 40m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Tue 11/17
9:50 am-10:26 pm
2 stops11h 36m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 11/2
6:30 am-8:15 pm
1 stop12h 45m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$202
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 11/2
3:50 pm-11:35 am
2 stops18h 45m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$244
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Tue 10/6
7:11 am-1:55 pm
3 stops30h 44m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$296
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sun 10/11
6:00 am-1:55 pm
3 stops55h 55m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$331
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sat 10/3
6:20 am-1:55 pm
3 stops31h 35m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$341
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sun 10/11
6:24 am-1:55 pm
3 stops31h 31m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$342
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sat 10/3
6:40 am-8:10 pm
1 stop13h 30m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$377
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 11/2
5:00 am-3:23 pm
1 stop9h 23m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$377
Showing 1-10 of 37 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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
MDW-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
MDW-KIN
What is the cheapest month to book a flight from Chicago to Kingston?
Currently, November is the cheapest month in which you can book a flight from Chicago to Kingston (average of $433). Flying from Chicago to Kingston in December is currently the most expensive (average of $814). 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.
How much does it cost to fly round-trip from Chicago to Kingston?
Airfare is below average for this route at the moment.
Chicago to Kingston flights typically cost between $498 and $552 in October.The cheapest round-trip price found within the last 5 days was $472 on Air Canada (Oct 8-Oct 15).
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 September 24, 2026.
Read through reviews of airlines operating flights from Chicago to Kingston, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Entertainment
6.8
Boarding
7.4
Crew
7.9
Comfort
7.2
Overall
7.0
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Food
6.4
Entertainment
6.8
Boarding
7.4
Crew
7.9
Comfort
7.2
Overall
7.0
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
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
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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 September 24, 2026.
Chicago and Kingston flights
Browse other Chicago and Kingston flight options. Last updated on September 24, 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 September 24, 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 September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$433 | Average$673 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$445 | Average$638 | FlexibilityNo cancel fee | On-timeN/A |