$210+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Jamaica to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 October 30, 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 October 30, 2026.
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/231:50 pm -
1 stop20h 33m
Sun 11/298:40 pm -
1 stop19h 40m
Deal found 10/26![Air Canada logo]()
$377
This Trip.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Fri 11/202:20 pm -
1 stop30h 32m
Sun 11/2910:15 am -
1 stop25h 35m
Deal found 10/28![Air Canada logo]()
$386
This Orbitz deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/194:43 pm -
1 stop8h 30m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/26![Frontier logo]()
$392
This Travelocity deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Wed 11/251:50 pm -
1 stop28h 53m
Wed 12/28:45 am -
1 stop7h 35m
Deal found 10/26![Air Canada logo]()
$394
This Expedia deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/124:43 pm -
1 stop17h 31m
Thu 11/267:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$405
This Priceline deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/64:23 pm -
1 stop21h 28m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$407
This Priceline deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates ” 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 11/134:23 pm -
1 stop21h 28m
Thu 11/267:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$413
This Expedia deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Sat 11/74:43 pm -
1 stop8h 04m
Tue 11/249:09 am -
1 stop26h 47m
Deal found 10/29![Frontier logo]()
$420
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/202:01 pm -
1 stop24h 44m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$430
This FlightHub deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/122:22 pm -
1 stop26h 44m
Sat 1/21:11 pm -
1 stop23h 33m
Deal found 10/30![Frontier logo]()
$455
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/194:43 pm -
1 stop20h 12m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$467
This Copa Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/122:58 pm -
1 stop10h 13m
Wed 11/252:13 pm -
1 stop22h 39m
Deal found 10/29![Copa Airlines logo]()
$521
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 October 30, 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 October 30, 2026.
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/298:40 pm -
1 stop19h 40m
Deal found 10/26![Air Canada logo]()
$380
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/202:01 pm -
1 stop24h 44m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$430
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 4/221:52 pm -
Nonstop4h 23m
Wed 4/286:00 am -
1 stop7h 10m
Deal found 10/25![United Airlines logo]()
$457
This Copa Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/122:58 pm -
1 stop10h 13m
Wed 11/252:13 pm -
1 stop22h 39m
Deal found 10/29![Copa Airlines logo]()
$521
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/253:45 pm -
2 stops9h 35m
Wed 12/26:00 am -
1 stop7h 25m
Deal found 10/26![Southwest logo]()
$571
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/194:15 pm -
1 stop18h 08m
Sun 11/228:45 am -
1 stop9h 10m
Deal found 10/26![Multiple Airlines logo]()
$690
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/127:08 am -
2 stops11h 19m
Wed 11/2511:00 am -
2 stops10h 23m
Deal found 10/29![American Airlines logo]()
$750
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/259:00 am -
1 stop8h 18m
Mon 11/3011:27 am -
1 stop7h 33m
Deal found 10/28![Delta logo]()
$894
This FlightHub deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/122:22 pm -
1 stop26h 44m
Sat 1/21:11 pm -
1 stop23h 33m
Deal found 10/30![Frontier logo]()
$455
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 10/28![United Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Fri 11/201:50 pm -
2 stops10h 20m
Sun 11/228:40 pm -
2 stops16h 45m
Deal found 10/26![Southwest logo]()
$601
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Thu 11/123:25 pm -
1 stop8h 50m
Wed 11/255:25 am -
1 stop8h 20m
Deal found 10/29![Southwest logo]()
$624
This Justfly.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/304:30 pm -
2 stops26h 31m
Tue 12/299:29 am -
2 stops29h 01m
Deal found 10/26![WestJet logo]()
$1,423
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/127:00 am -
1 stop13h 54m
Mon 3/157:47 pm -
1 stop13h 28m
Deal found 10/25![American Airlines logo]()
$753
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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.
Fri 11/271:50 pm -
2 stops9h 55m
Sun 11/298:40 pm -
2 stops15h 10m
Deal found 10/30![Southwest logo]()
$698
This Booking.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:10 am -
3 stops15h 08m
Mon 11/307:49 am -
3 stops28h 21m
Deal found 10/28![Multiple Airlines logo]()
$860
This Mytrip deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/1210:01 am -
3 stops23h 45m
Wed 11/258:45 am -
1 stop9h 00m
Deal found 10/29![Multiple Airlines logo]()
$865
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/102:58 pm -
1 stop10h 13m
Fri 11/132:13 pm -
1 stop22h 39m
Deal found 10/27![United Airlines logo]()
$867
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/292:55 pm -
1 stop7h 55m
Sun 12/68:40 pm -
2 stops16h 45m
Deal found 10/30![Southwest logo]()
$767
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/129:00 am -
1 stop8h 18m
Wed 11/2511:27 am -
1 stop7h 33m
Deal found 10/29![Delta logo]()
$1,032
This Mytrip deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/101:50 pm -
3 stops34h 57m
Wed 11/258:42 pm -
3 stops39h 43m
Deal found 10/29![Multiple Airlines logo]()
$867
This Booking.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:12 am -
3 stops24h 02m
Mon 11/309:09 am -
3 stops27h 01m
Deal found 10/28![Multiple Airlines logo]()
$873
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/289:00 am -
1 stop14h 54m
Sat 12/56:00 am -
1 stop13h 00m
Deal found 10/28![Delta logo]()
$1,057
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Fri 12/113:45 pm -
1 stop8h 15m
Fri 12/187:10 am -
1 stop6h 15m
Deal found 10/27![Southwest logo]()
$882
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/309:00 am -
1 stop8h 18m
Tue 12/299:58 am -
1 stop9h 02m
Deal found 10/26![Delta logo]()
$1,504
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/129:00 am -
1 stop7h 04m
Sat 12/196:00 am -
1 stop13h 00m
Deal found 10/28![Delta logo]()
$1,995
Last-minute flights from Jamaica to ChicagoDiscover last-minute flight deals from Jamaica to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Jamaica to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/64:23 pm -
1 stop21h 28m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$407
This Copa Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/62:58 pm -
1 stop10h 13m
Thu 11/122:13 pm -
1 stop22h 39m
Deal found 10/25![Copa Airlines logo]()
$534
This Expedia deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Sat 11/74:43 pm -
1 stop8h 04m
Tue 11/249:09 am -
1 stop26h 47m
Deal found 10/29![Frontier logo]()
$420
This Expedia deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/124:43 pm -
1 stop17h 31m
Thu 11/267:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$405
This Copa Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/122:58 pm -
1 stop10h 13m
Wed 11/252:13 pm -
1 stop22h 39m
Deal found 10/29![Copa Airlines logo]()
$521
This Priceline deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/134:23 pm -
1 stop21h 28m
Thu 11/267:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$413
This Orbitz deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/194:43 pm -
1 stop8h 30m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/26![Frontier logo]()
$392
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/194:43 pm -
1 stop20h 12m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$467
This Trip.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Fri 11/202:20 pm -
1 stop30h 32m
Sun 11/2910:15 am -
1 stop25h 35m
Deal found 10/28![Air Canada logo]()
$386
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/202:01 pm -
1 stop24h 44m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$430
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/231:50 pm -
1 stop20h 33m
Sun 11/298:40 pm -
1 stop19h 40m
Deal found 10/26![Air Canada logo]()
$377
This Travelocity deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Wed 11/251:50 pm -
1 stop28h 53m
Wed 12/28:45 am -
1 stop7h 35m
Deal found 10/26![Air Canada logo]()
$394
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 October 30, 2026.
Search for one-way flight options from Jamaica to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/272:35 pm -
Nonstop4h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$210
This Trip.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Sat 11/71:50 pm -
1 stop20h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Air Canada logo]()
$217
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/61:16 pm -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Sat 12/52:22 pm -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$233
This Travelocity deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Wed 12/162:20 pm -
1 stop30h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Air Canada logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Sat 11/212:01 pm -
1 stop10h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$237
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/32:18 pm -
1 stop26h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$238
This Travelocity deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Mon 11/96:20 pm -
1 stop24h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Air Canada logo]()
$240
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/74:43 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$241
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Sun 12/62:22 pm -
1 stop26h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$249
This Priceline deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/212:01 pm -
1 stop19h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Tue 12/222:59 pm -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$254
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $377 (Air Canada) |
One-way from | $210 (American Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $469 |
Good round-trip deal | $461 or less |
Good one-way deal | $294 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 October 30, 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
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Fri 12/25
8:00 am-5:44 pm
2 stops10h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Wed 12/23
8:00 am-4:19 pm
1 stop9h 19m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
Quickest round-trip
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Sun 1/31
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$280
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Thu 1/21
6:09 pm-11:55 pm
1 stop6h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$280
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Wed 2/3
6:09 pm-10:04 am
1 stop16h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$284
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Fri 2/5
12:39 pm-11:55 pm
1 stop12h 16m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$284
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Tue 2/2
3:35 pm-12:45 pm
2 stops22h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$287
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Mon 2/1
6:09 pm-11:55 pm
1 stop6h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$290
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Sat 1/30
3:35 pm-2:00 pm
2 stops23h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$293
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Mon 11/9
4:23 pm-11:47 pm
1 stop8h 24m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$297
Showing 1-10 of 56 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-ORD
MBJ-MDW
KIN-ORD
KIN-MDW
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-ORD
MBJ-MDW
KIN-ORD
KIN-MDW
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 $367). Flying from Jamaica to Chicago in August is currently the most expensive (average of $643). 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 October 30, 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.
Boarding
7.4
Overall
7.0
Comfort
7.2
Entertainment
6.8
Food
6.4
Crew
7.9
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Boarding
7.4
Overall
7.0
Comfort
7.2
Entertainment
6.8
Food
6.4
Crew
7.9
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
Merrillville
Lansing
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 October 30, 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 October 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Jamaica to Chicago
Discover the top 2 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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$281 | Average$431 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$281 | Average$587 | FlexibilityNo cancel fee | On-time71% |