$159+ Cheap flights from Chicago (CHI) to Jamaica
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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Jamaica with Cheapflights
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Cheapest flights from Chicago to JamaicaExplore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/178:55 pm -
1 stop14h 13m
Fri 10/2312:18 pm -
1 stop9h 12m
Deal found 9/10![American Airlines logo]()
$430
This FlightHub deal was found by Cheapflights users on 9/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:15 am -
1 stop7h 13m
Tue 11/31:50 pm -
1 stop24h 23m
Deal found 9/13![Multiple Airlines logo]()
$431
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop7h 13m
Mon 11/236:20 pm -
2 stops14h 40m
Deal found 9/14![Multiple Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/109:29 pm -
1 stop18h 43m
Wed 10/145:13 pm -
1 stop16h 17m
Deal found 9/10![American Airlines logo]()
$438
This JetBlue deal was found by Cheapflights users on 9/14. 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 11/87:00 am -
1 stop6h 57m
Sat 11/213:00 pm -
1 stop9h 38m
Deal found 9/14![JetBlue logo]()
$439
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/315:29 pm -
1 stop16h 46m
Tue 11/33:56 pm -
Nonstop4h 50m
Deal found 9/10![American Airlines logo]()
$440
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:46 pm -
1 stop17h 16m
Fri 10/303:23 pm -
1 stop8h 24m
Deal found 9/14![Frontier logo]()
$441
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 11/309:37 am -
Nonstop4h 12m
Wed 2/173:46 pm -
1 stop16h 39m
Deal found 9/14![American Airlines logo]()
$441
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop8h 18m
Mon 10/263:48 pm -
1 stop7h 55m
Deal found 9/14![Frontier logo]()
$442
This Travelocity deal was found by Cheapflights users on 9/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:44 pm -
1 stop18h 49m
Sun 10/251:20 pm -
2 stops20h 03m
Deal found 9/10![Multiple Airlines logo]()
$442
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 pm -
2 stops18h 04m
Sat 10/313:50 pm -
1 stop18h 06m
Deal found 9/11![Multiple Airlines logo]()
$443
This Expedia deal was found by Cheapflights users on 9/14. 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.
Fri 11/67:50 pm -
1 stop18h 38m
Mon 11/96:20 pm -
1 stop26h 38m
Deal found 9/14![Multiple Airlines logo]()
$444
Best flights from Chicago to JamaicaDiscover carefully curated flight deals from Chicago to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
Discover carefully curated flight deals from Chicago to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
This United Airlines deal was found by Cheapflights users on 9/13. 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 11/235:00 am -
1 stop8h 14m
Wed 12/22:54 pm -
Nonstop4h 26m
Deal found 9/13![United Airlines logo]()
$472
This JetBlue deal was found by Cheapflights users on 9/14. 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 10/187:00 am -
1 stop7h 05m
Mon 10/1912:01 pm -
1 stop11h 29m
Deal found 9/14![JetBlue logo]()
$477
This Delta deal was found by Cheapflights users on 9/14. 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 11/146:00 am -
1 stop9h 57m
Sat 11/212:16 pm -
1 stop9h 38m
Deal found 9/14![Delta logo]()
$482
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:30 am -
1 stop6h 25m
Fri 10/3012:00 pm -
2 stops11h 10m
Deal found 9/14![Southwest logo]()
$487
This Copa Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 1/127:35 am -
1 stop26h 44m
Tue 1/1912:18 pm -
1 stop25h 28m
Deal found 9/10![Copa Airlines logo]()
$489
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/45:56 pm -
2 stops40h 39m
Tue 1/1212:45 pm -
2 stops30h 39m
Deal found 9/14![Air Canada logo]()
$649
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am -
1 stop27h 32m
Sat 10/248:06 pm -
1 stop26h 04m
Deal found 9/10![Arajet logo]()
$665
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:55 am -
1 stop7h 19m
Tue 11/172:54 pm -
Nonstop4h 26m
Deal found 9/12![United Airlines logo]()
$472
This JetBlue deal was found by Cheapflights users on 9/13. 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 11/187:00 am -
1 stop6h 57m
Wed 11/253:00 pm -
1 stop9h 38m
Deal found 9/13![JetBlue logo]()
$481
This Delta deal was found by Cheapflights users on 9/13. 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 11/136:15 pm -
2 stops17h 15m
Tue 11/171:55 pm -
1 stop8h 47m
Deal found 9/13![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:55 pm -
2 stops14h 55m
Thu 10/2212:50 pm -
1 stop9h 10m
Deal found 9/10![Southwest logo]()
$490
This Copa Airlines deal was found by Cheapflights users on 9/12. 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 10/283:13 pm -
1 stop22h 42m
Wed 11/112:58 pm -
1 stop22h 48m
Deal found 9/12![Copa Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Sun 11/88:40 am -
Nonstop4h 08m
Thu 11/192:54 pm -
Nonstop4h 26m
Deal found 9/14![United Airlines logo]()
$480
This JetBlue deal was found by Cheapflights users on 9/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am -
1 stop5h 48m
Thu 11/122:58 pm -
1 stop9h 57m
Deal found 9/11![JetBlue logo]()
$486
This Delta deal was found by Cheapflights users on 9/13. 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 11/135:05 pm -
2 stops18h 25m
Thu 11/196:12 pm -
1 stop6h 42m
Deal found 9/13![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:05 am -
2 stops8h 40m
Fri 11/201:50 pm -
2 stops10h 20m
Deal found 9/14![Southwest logo]()
$503
This Copa Airlines deal was found by Cheapflights users on 9/13. 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
Wed 10/212:57 pm -
1 stop10h 00m
Deal found 9/13![Copa Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 9/14. 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 11/138:40 am -
Nonstop4h 08m
Sat 11/212:54 pm -
Nonstop4h 26m
Deal found 9/14![United Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:27 am -
1 stop6h 24m
Tue 11/106:12 pm -
2 stops14h 34m
Deal found 9/10![Delta logo]()
$490
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:10 am -
1 stop8h 30m
Thu 10/2210:30 am -
1 stop11h 40m
Deal found 9/10![JetBlue logo]()
$502
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/168:40 am -
1 stop6h 39m
Sat 1/233:45 pm -
1 stop8h 14m
Deal found 9/11![United Airlines logo]()
$483
This Copa Airlines deal was found by Cheapflights users on 9/14. 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 9/14![Copa Airlines logo]()
$557
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:20 pm -
2 stops14h 30m
Wed 10/2812:00 pm -
2 stops10h 15m
Deal found 9/13![Southwest logo]()
$561
This Delta deal was found by Cheapflights users on 9/14. 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 1/236:00 am -
1 stop7h 10m
Sat 1/303:40 pm -
1 stop7h 30m
Deal found 9/14![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 1/98:40 am -
1 stop6h 39m
Sat 1/165:21 pm -
1 stop7h 38m
Deal found 9/13![United Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:55 am -
1 stop6h 30m
Sat 10/312:55 pm -
1 stop9h 20m
Deal found 9/14![Southwest logo]()
$599
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:00 am -
1 stop6h 50m
Sat 12/121:25 pm -
2 stops9h 55m
Deal found 9/13![Southwest logo]()
$606
This Delta deal was found by Cheapflights users on 9/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:04 am -
1 stop5h 47m
Tue 11/102:16 pm -
1 stop9h 38m
Deal found 9/12![Delta logo]()
$613
This Copa Airlines deal was found by Cheapflights users on 9/14. 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 2/252:13 pm -
1 stop22h 39m
Sun 2/283:05 pm -
1 stop10h 03m
Deal found 9/14![Copa Airlines logo]()
$727
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/97:55 am -
Nonstop3h 55m
Sat 1/161:25 pm -
Nonstop4h 05m
Deal found 9/13![Southwest logo]()
$611
Last-minute flights from Chicago to JamaicaDiscover last-minute flight deals from Chicago to Jamaica. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jamaica. Data last updated September 15, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:46 pm -
1 stop17h 16m
Fri 10/303:23 pm -
1 stop8h 24m
Deal found 9/14![Frontier logo]()
$441
This Justfly.com deal was found by Cheapflights users on 9/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 am -
1 stop7h 37m
Sat 10/103:48 pm -
1 stop7h 55m
Deal found 9/14![Frontier logo]()
$445
This JetBlue deal was found by Cheapflights users on 9/14. 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 10/56:00 am -
1 stop6h 03m
Sat 10/1012:03 pm -
1 stop11h 27m
Deal found 9/14![JetBlue logo]()
$445
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/109:29 pm -
1 stop18h 43m
Wed 10/145:13 pm -
1 stop16h 17m
Deal found 9/10![American Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/178:55 pm -
1 stop14h 13m
Fri 10/2312:18 pm -
1 stop9h 12m
Deal found 9/10![American Airlines logo]()
$430
This Travelocity deal was found by Cheapflights users on 9/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:44 pm -
1 stop18h 49m
Sun 10/251:20 pm -
2 stops20h 03m
Deal found 9/10![Multiple Airlines logo]()
$442
This Expedia deal was found by Cheapflights users on 9/14. 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.
Thu 10/227:44 pm -
1 stop18h 49m
Tue 10/2712:50 pm -
1 stop20h 33m
Deal found 9/14![Multiple Airlines logo]()
$444
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop8h 18m
Mon 10/263:48 pm -
1 stop7h 55m
Deal found 9/14![Frontier logo]()
$442
This Travelocity deal was found by Cheapflights users on 9/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:00 pm -
2 stops46h 25m
Mon 10/263:48 pm -
1 stop21h 03m
Deal found 9/10![Multiple Airlines logo]()
$446
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 pm -
2 stops18h 04m
Sat 10/313:50 pm -
1 stop18h 06m
Deal found 9/11![Multiple Airlines logo]()
$443
This FlightHub deal was found by Cheapflights users on 9/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:15 am -
1 stop7h 13m
Tue 11/31:50 pm -
1 stop24h 23m
Deal found 9/13![Multiple Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/315:29 pm -
1 stop16h 46m
Tue 11/33:56 pm -
Nonstop4h 50m
Deal found 9/10![American Airlines logo]()
$440
One-way flights from Chicago to JamaicaSearch for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 11/148:40 am -
Nonstop4h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/135:00 am -
1 stop8h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$163
This Super.com deal was found by Cheapflights users on 9/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$175
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Sat 10/107:00 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$176
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:25 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$177
This FlightHub deal was found by Cheapflights users on 9/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:28 pm -
1 stop16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$179
This Trip.com deal was found by Cheapflights users on 9/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:24 am -
1 stop8h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$179
This Air Canada deal was found by Cheapflights users on 9/14. 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.
Sat 12/121:55 pm -
2 stops23h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Air Canada logo]()
$181
This CheapOair deal was found by Cheapflights users on 9/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$182
This Expedia deal was found by Cheapflights users on 9/13. 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.
Fri 11/275:58 pm -
2 stops42h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Air Canada logo]()
$184
This FlightHub deal was found by Cheapflights users on 9/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/119:21 pm -
1 stop14h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$189
Find flight deals from Chicago to Jamaica
Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $430 (American Airlines) |
One-way from | $159 (United Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $460 |
Good round-trip deal | $482 or less |
Good one-way deal | $202 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Jamaica 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 15, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 1/12
6:00 am-3:25 pm
1 stop8h 25m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 9/28
5:55 am-1:15 pm
2 stops7h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/8
6:00 am-4:57 pm
1 stop9h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 12/6
6:00 am-4:57 pm
1 stop9h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 10/6
6:04 am-1:00 pm
1 stop6h 56m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sat 1/2
5:30 am-8:41 pm
1 stop14h 11m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 3/8
1:35 pm-11:05 am
2 stops20h 30m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Tue 1/12
6:00 am-2:45 pm
1 stop7h 45m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sat 2/20
11:10 am-7:40 pm
1 stop7h 30m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$210
Quickest round-trip
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Fri 11/6
8:40 am-1:48 pm
Nonstop4h 08m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
ORD-MBJ
MDW-MBJ
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 Jamaica
CHI-JM0
ORD-MBJ
MDW-MBJ
ORD-KIN
MDW-KIN
What is the cheapest month to book a flight from Chicago to Jamaica?
Currently, April is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $478). Flying from Chicago to Jamaica in December is currently the most expensive (average of $657). 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 far ahead should I book a flight from Chicago to Jamaica?
Booking 13 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Jamaica. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated September 15, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 Jamaica
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jamaica by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Jamaica by cabin class
Find flights from Chicago to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Jamaica flights
Browse other Chicago and Jamaica flight options. Last updated on September 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Jamaica flights
Consider these flights traveling from Chicago to Jamaica.
Top 6 airlines flying from Chicago to Jamaica
Discover the top 6 airlines that operate flights from Chicago to Jamaica. 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$462 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$592 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$297 | Average$510 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$302 | Average$547 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$317 | Average$607 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |