$199+ Cheap flights from Jamaica to Chicago (CHI)
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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from Jamaica to Chicago with Cheapflights
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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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Cheapest flights from Jamaica to ChicagoExplore the most affordable flight options available from Jamaica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
Explore the most affordable flight options available from Jamaica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
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.
Thu 10/2212:13 pm -
1 stop10h 47m
Sun 10/256:55 am -
1 stop9h 17m
Deal found 9/14![American Airlines logo]()
$326
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:48 pm -
1 stop7h 55m
Sun 10/256:24 am -
1 stop8h 09m
Deal found 9/14![Frontier logo]()
$368
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/232:54 pm -
Nonstop4h 26m
Sun 11/298:40 am -
Nonstop4h 08m
Deal found 9/16![United Airlines logo]()
$371
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:30 pm -
1 stop20h 30m
Mon 10/268:45 am -
1 stop7h 35m
Deal found 9/13![Air Canada logo]()
$372
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:20 pm -
1 stop16h 03m
Sun 11/294:30 pm -
1 stop23h 50m
Deal found 9/15![Air Canada logo]()
$373
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 10/13:42 pm -
1 stop8h 02m
Sun 10/186:24 am -
1 stop8h 09m
Deal found 9/14![Frontier logo]()
$385
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/112:52 pm -
1 stop10h 29m
Sun 10/186:25 am -
1 stop7h 05m
Deal found 9/16![United Airlines logo]()
$386
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/311:44 pm -
2 stops10h 00m
Sat 11/75:54 pm -
1 stop15h 21m
Deal found 9/16![American Airlines logo]()
$391
This Justfly.com deal was found by Cheapflights users on 9/16. 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.
Wed 11/181:50 pm -
1 stop28h 53m
Mon 11/307:03 am -
1 stop9h 17m
Deal found 9/16![Air Canada logo]()
$392
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:43 pm -
1 stop8h 04m
Sat 11/147:25 am -
1 stop7h 03m
Deal found 9/12![Frontier logo]()
$405
This Southwest deal was found by Cheapflights users on 9/16. 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.
Wed 11/181:50 pm -
1 stop8h 30m
Mon 11/305:25 am -
1 stop8h 20m
Deal found 9/16![Southwest logo]()
$436
This Air Canada deal was found by Cheapflights users on 9/16. 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 11/114:00 pm -
2 stops27h 30m
Wed 11/255:58 pm -
2 stops40h 37m
Deal found 9/16![Air Canada logo]()
$457
Best flights from Jamaica to ChicagoDiscover carefully curated flight deals from Jamaica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Jamaica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:48 pm -
1 stop7h 55m
Sun 10/256:24 am -
1 stop8h 09m
Deal found 9/14![Frontier logo]()
$368
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.
Mon 11/232:54 pm -
Nonstop4h 26m
Sun 11/298:40 am -
Nonstop4h 08m
Deal found 9/15![United Airlines logo]()
$371
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:30 pm -
1 stop20h 30m
Mon 10/268:45 am -
1 stop7h 35m
Deal found 9/13![Air Canada logo]()
$372
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/311:44 pm -
2 stops10h 00m
Sat 11/75:54 pm -
1 stop15h 21m
Deal found 9/16![American Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 9/16. 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.
Wed 11/181:00 pm -
1 stop9h 30m
Mon 11/305:20 am -
2 stops8h 25m
Deal found 9/16![Southwest logo]()
$436
This Copa Airlines deal was found by Cheapflights users on 9/16. 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 11/112:58 pm -
1 stop22h 48m
Wed 11/252:13 pm -
1 stop22h 39m
Deal found 9/16![Copa Airlines logo]()
$478
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:02 pm -
1 stop7h 53m
Mon 11/167:00 am -
1 stop5h 48m
Deal found 9/15![JetBlue logo]()
$560
This Priceline deal was found by Cheapflights users on 9/16. 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.
Thu 1/2112:45 pm -
2 stops20h 15m
Wed 1/277:00 am -
1 stop6h 06m
Deal found 9/16![Multiple Airlines logo]()
$617
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:20 pm -
2 stops17h 47m
Sun 11/295:58 pm -
2 stops22h 22m
Deal found 9/12![Air Canada logo]()
$381
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/112:52 pm -
1 stop10h 29m
Sun 10/186:25 am -
1 stop7h 05m
Deal found 9/16![United Airlines logo]()
$386
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:43 pm -
1 stop8h 04m
Sat 11/147:25 am -
1 stop7h 03m
Deal found 9/12![Frontier logo]()
$405
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/12:20 pm -
1 stop21h 47m
Sat 11/143:45 pm -
1 stop20h 40m
Deal found 9/12![Air Canada logo]()
$407
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.
Thu 10/2212:52 pm -
1 stop10h 29m
Sun 10/258:40 am -
Nonstop4h 08m
Deal found 9/14![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 9/16. 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 11/31:00 pm -
1 stop9h 25m
Fri 11/138:40 pm -
2 stops16h 25m
Deal found 9/16![Southwest logo]()
$476
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:08 am -
2 stops12h 22m
Mon 11/96:05 pm -
1 stop20h 17m
Deal found 9/13![American Airlines logo]()
$480
This Copa Airlines deal was found by Cheapflights users on 9/16. 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 1/213:01 pm -
1 stop10h 06m
Mon 1/252:13 pm -
1 stop22h 40m
Deal found 9/16![Copa Airlines logo]()
$538
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.
Wed 10/2112:00 pm -
1 stop6h 35m
Mon 10/265:00 am -
1 stop6h 50m
Deal found 9/13![Southwest logo]()
$490
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:00 pm -
2 stops27h 30m
Wed 11/255:58 pm -
2 stops40h 37m
Deal found 9/13![Air Canada logo]()
$458
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/192:25 pm -
1 stop17h 36m
Thu 12/319:23 pm -
1 stop14h 45m
Deal found 9/15![Frontier logo]()
$532
This Priceline deal was found by Cheapflights users on 9/16. 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.
Thu 1/2112:45 pm -
2 stops20h 15m
Mon 1/257:45 pm -
1 stop12h 30m
Deal found 9/16![Multiple Airlines logo]()
$617
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.
Wed 10/2812:50 pm -
1 stop8h 35m
Wed 11/46:00 am -
1 stop7h 25m
Deal found 9/13![Southwest logo]()
$536
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.
Thu 10/293:00 pm -
2 stops20h 07m
Thu 11/54:30 pm -
1 stop18h 05m
Deal found 9/14![Air Canada logo]()
$510
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:03 pm -
1 stop7h 35m
Fri 10/167:29 pm -
1 stop15h 28m
Deal found 9/12![American Airlines logo]()
$618
This Trip.com deal was found by Cheapflights users on 9/16. 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 1/2112:45 pm -
1 stop21h 23m
Wed 1/2712:50 pm -
1 stop21h 45m
Deal found 9/16![Air Canada logo]()
$576
This Air Canada deal was found by Cheapflights users on 9/16. 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.
Thu 1/2112:45 pm -
2 stops20h 15m
Mon 1/251:55 pm -
2 stops20h 40m
Deal found 9/16![Air Canada logo]()
$623
Last-minute flights from Jamaica to ChicagoDiscover last-minute flight deals from Jamaica to Chicago. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Jamaica to Chicago. Data last updated September 17, 2026 and is based on user searches.
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 10/13:42 pm -
1 stop8h 02m
Sun 10/186:24 am -
1 stop8h 09m
Deal found 9/14![Frontier logo]()
$385
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/112:52 pm -
1 stop10h 29m
Sun 10/186:25 am -
1 stop7h 05m
Deal found 9/16![United Airlines logo]()
$386
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.
Thu 10/112:05 pm -
1 stop12h 09m
Sun 10/185:00 am -
1 stop11h 12m
Deal found 9/14![American Airlines logo]()
$436
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.
Thu 10/14:50 pm -
2 stops15h 06m
Sun 10/185:27 am -
1 stop10h 00m
Deal found 9/14![Delta logo]()
$437
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:30 pm -
1 stop20h 30m
Mon 10/268:45 am -
1 stop7h 35m
Deal found 9/13![Air Canada logo]()
$372
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.
Thu 10/2212:13 pm -
1 stop10h 47m
Sun 10/256:55 am -
1 stop9h 17m
Deal found 9/14![American Airlines logo]()
$326
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:48 pm -
1 stop7h 55m
Sun 10/256:24 am -
1 stop8h 09m
Deal found 9/14![Frontier logo]()
$368
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.
Thu 10/2212:52 pm -
1 stop10h 29m
Sun 10/258:40 am -
Nonstop4h 08m
Deal found 9/14![United Airlines logo]()
$422
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:13 pm -
1 stop14h 34m
Wed 11/46:00 am -
1 stop10h 09m
Deal found 9/13![American Airlines logo]()
$431
This Priceline deal was found by Cheapflights users on 9/16. 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 10/313:50 pm -
1 stop18h 06m
Sat 11/77:15 am -
1 stop7h 13m
Deal found 9/16![Frontier logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/311:44 pm -
2 stops10h 00m
Sat 11/75:54 pm -
1 stop15h 21m
Deal found 9/16![American Airlines logo]()
$391
This Air Canada deal was found by Cheapflights users on 9/16. 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 10/315:20 pm -
2 stops18h 47m
Sat 11/75:58 pm -
2 stops18h 27m
Deal found 9/16![Air Canada logo]()
$428
One-way flights from Jamaica to ChicagoSearch for one-way flight options from Jamaica to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Jamaica to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. 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 11/132:54 pm -
Nonstop4h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![United Airlines logo]()
$199
This JetBlue deal was found by Cheapflights users on 9/16. 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 11/181:07 pm -
1 stop11h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![JetBlue logo]()
$203
This Trip.com deal was found by Cheapflights users on 9/16. 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 10/1512:30 pm -
1 stop26h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$204
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/23:56 pm -
Nonstop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$209
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.
Wed 1/131:26 pm -
1 stop10h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$210
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2711:07 am -
1 stop13h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$220
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.
Sun 12/133:20 pm -
1 stop28h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Air Canada logo]()
$223
This Super.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/163:48 pm -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$224
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:43 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$227
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.
Fri 12/112:20 pm -
2 stops29h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Air Canada logo]()
$228
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:48 pm -
1 stop17h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$230
This Air Canada deal was found by Cheapflights users on 9/16. 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.
Mon 11/26:20 pm -
2 stops17h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$231
Find flight deals from Jamaica to Chicago
Keep the following information in mind while searching for Jamaica to Chicago flight deals. Data was last updated September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $326 (American Airlines) |
One-way from | $199 (United Airlines) |
Good round-trip deal | $540 or less |
Good one-way deal | $295 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Jamaica to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 17, 2026.
Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Wed 11/18
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$199
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Thu 11/19
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$199
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Thu 11/19
3:00 pm-11:38 pm
1 stop9h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$203
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Fri 11/13
6:12 pm-1:59 pm
2 stops20h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$219
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Wed 11/18
6:12 pm-1:59 pm
2 stops20h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$219
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Tue 12/15
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Thu 12/10
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Thu 12/17
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Thu 3/11
2:48 pm-6:16 pm
Nonstop4h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$260
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Tue 3/9
3:20 pm-10:58 pm
1 stop8h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$260
Showing 1-10 of 52 resultsSorted by cheapest first
Best time to book a flight from Jamaica to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Jamaica with our price prediction graph.
MBJ-MDW
MBJ-ORD
KIN-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Jamaica to Chicago
JM0-CHI
MBJ-MDW
MBJ-ORD
KIN-ORD
What is the cheapest month to book a flight from Jamaica to Chicago?
Currently, December is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $300). Flying from Jamaica to Chicago in August is currently the most expensive (average of $605). 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 Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 17, 2026.
Peruse reviews from past customers who have flown with American Airlines from Jamaica to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.1
Boarding
7.4
Crew
7.9
Entertainment
6.8
Food
6.4
Comfort
7.2
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Overall
7.1
Boarding
7.4
Crew
7.9
Entertainment
6.8
Food
6.4
Comfort
7.2
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Related info for your journey
Find useful and relevant information for your journey from Jamaica to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Jamaica to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Jamaica to Chicago by cabin class
Find flights from Jamaica to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jamaica and Chicago flights
Browse other Jamaica and Chicago flight options. Last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Jamaica to Chicago
Discover the top 4 airlines that operate flights from Jamaica to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$281 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$281 | Average$548 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$281 | Average$587 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$446 | Average$589 | FlexibilityNo cancel fee | On-time62% |