$184+ 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
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Jamaica 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 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 October 30, 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 October 30, 2026.
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:58 pm -
2 stops18h 27m
Tue 11/241:50 pm -
1 stop20h 33m
Deal found 10/27![Air Canada logo]()
$465
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.
Sat 10/313:45 pm -
2 stops21h 05m
Tue 11/31:50 pm -
1 stop20h 33m
Deal found 10/26![Air Canada logo]()
$468
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.
Mon 11/166:08 am -
1 stop8h 00m
Mon 11/232:01 pm -
1 stop19h 13m
Deal found 10/28![Frontier logo]()
$469
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 10/317:15 am -
1 stop7h 13m
Tue 11/31:50 pm -
1 stop27h 54m
Deal found 10/27![Multiple Airlines logo]()
$469
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.
Sat 11/145:58 pm -
2 stops18h 27m
Thu 11/191:50 pm -
2 stops19h 10m
Deal found 10/26![Air Canada logo]()
$470
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.
Sat 12/54:30 pm -
1 stop18h 46m
Wed 12/911:05 am -
1 stop8h 20m
Deal found 10/28![American Airlines logo]()
$471
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
1 stop23h 49m
Thu 12/102:22 pm -
1 stop26h 44m
Deal found 10/30![Frontier logo]()
$472
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.
Wed 12/25:58 pm -
2 stops42h 27m
Sun 12/62:22 pm -
1 stop8h 20m
Deal found 10/28![Multiple Airlines logo]()
$472
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:50 pm -
1 stop16h 06m
Mon 11/236:20 pm -
1 stop16h 24m
Deal found 10/27![Multiple Airlines logo]()
$474
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 12/69:40 am -
Nonstop4h 13m
Wed 12/93:58 pm -
Nonstop4h 47m
Deal found 10/28![American Airlines logo]()
$476
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 11/126:42 pm -
1 stop19h 26m
Mon 11/232:01 pm -
1 stop23h 20m
Deal found 10/27![Frontier logo]()
$477
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:45 am -
2 stops27h 40m
Mon 11/236:20 pm -
2 stops25h 10m
Deal found 10/27![Air Canada logo]()
$478
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 October 30, 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 October 30, 2026.
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.
Mon 2/227:35 am -
1 stop26h 40m
Mon 3/112:20 pm -
1 stop25h 26m
Deal found 10/25![Copa Airlines logo]()
$500
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/167:00 am -
1 stop6h 05m
Tue 2/233:00 pm -
1 stop9h 37m
Deal found 10/29![JetBlue logo]()
$509
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.
Sun 1/247:00 am -
2 stops8h 44m
Wed 2/36:09 pm -
2 stops19h 55m
Deal found 10/28![Delta logo]()
$516
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:25 am -
1 stop8h 20m
Wed 12/21:50 pm -
1 stop6h 45m
Deal found 10/28![Southwest logo]()
$525
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.
Mon 2/228:40 am -
Nonstop4h 08m
Mon 3/11:25 pm -
1 stop9h 28m
Deal found 10/25![United Airlines logo]()
$547
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/206:00 am -
1 stop8h 35m
Sat 2/2712:45 pm -
1 stop9h 40m
Deal found 10/30![American Airlines logo]()
$687
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/177:50 pm -
1 stop12h 48m
Sat 1/232:41 pm -
1 stop10h 06m
Deal found 10/25![JetBlue logo]()
$515
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.
Fri 4/97:35 pm -
1 stop15h 55m
Tue 4/132:25 pm -
2 stops17h 14m
Deal found 10/26![Delta logo]()
$522
This Copa Airlines 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:13 pm -
1 stop22h 39m
Sun 11/222:58 pm -
1 stop10h 13m
Deal found 10/30![Copa Airlines logo]()
$546
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/226:30 am -
1 stop6h 40m
Mon 3/14:00 pm -
1 stop8h 00m
Deal found 10/25![Southwest logo]()
$552
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.
Wed 3/178:39 am -
Nonstop4h 09m
Mon 3/221:54 pm -
Nonstop4h 26m
Deal found 10/28![United Airlines logo]()
$558
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 12/78:40 am -
Nonstop4h 08m
Sun 12/133:45 pm -
1 stop8h 10m
Deal found 10/28![United Airlines logo]()
$572
This Copa Airlines 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:13 pm -
1 stop22h 39m
Fri 12/43:03 pm -
1 stop22h 43m
Deal found 10/30![Copa Airlines logo]()
$586
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 2/176:35 am -
1 stop6h 35m
Wed 2/241:10 pm -
1 stop8h 35m
Deal found 10/26![Southwest logo]()
$589
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.
Sat 12/56:00 am -
1 stop9h 57m
Wed 12/92:19 pm -
1 stop9h 35m
Deal found 10/29![Delta logo]()
$599
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.
Wed 1/202:13 pm -
1 stop22h 40m
Wed 1/273:01 pm -
1 stop10h 06m
Deal found 10/25![Copa Airlines logo]()
$587
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:59 pm -
2 stops20h 59m
Thu 12/312:51 pm -
2 stops9h 33m
Deal found 10/27![American Airlines logo]()
$711
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.
Sat 1/238:40 am -
Nonstop4h 08m
Wed 1/272:54 pm -
Nonstop4h 26m
Deal found 10/28![United Airlines logo]()
$592
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/297:35 pm -
1 stop15h 55m
Sun 4/42:25 pm -
1 stop19h 08m
Deal found 10/27![Delta logo]()
$600
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.
Wed 12/26:00 am -
1 stop7h 25m
Sat 12/51:25 pm -
1 stop8h 00m
Deal found 10/29![Southwest logo]()
$645
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/202:13 pm -
1 stop22h 40m
Sun 1/243:01 pm -
1 stop10h 06m
Deal found 10/27![Copa Airlines logo]()
$587
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/165:59 pm -
1 stop17h 06m
Tue 2/2312:45 pm -
1 stop8h 09m
Deal found 10/27![American Airlines logo]()
$728
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 1/48:40 am -
Nonstop4h 08m
Mon 1/112:54 pm -
Nonstop4h 26m
Deal found 10/28![United Airlines logo]()
$604
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.
Thu 2/46:00 am -
1 stop9h 44m
Mon 2/86:09 pm -
1 stop6h 46m
Deal found 10/26![Delta logo]()
$606
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 1/282:13 pm -
1 stop22h 40m
Sun 1/313:01 pm -
1 stop10h 10m
Deal found 10/29![Copa Airlines logo]()
$587
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.
Sun 1/176:35 am -
1 stop6h 35m
Sat 1/2312:45 pm -
2 stops11h 00m
Deal found 10/29![Southwest logo]()
$658
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.
Sat 2/205:59 pm -
1 stop17h 06m
Tue 2/2312:45 pm -
1 stop8h 09m
Deal found 10/28![American Airlines logo]()
$728
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:40 am -
Nonstop4h 08m
Sun 12/62:54 pm -
Nonstop4h 26m
Deal found 10/29![United Airlines logo]()
$612
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:00 am -
1 stop6h 23m
Wed 12/96:01 am -
1 stop8h 29m
Deal found 10/29![JetBlue logo]()
$824
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/205:25 am -
1 stop6h 35m
Sun 1/242:00 pm -
1 stop8h 00m
Deal found 10/25![Southwest logo]()
$698
Last-minute flights from Chicago to JamaicaDiscover last-minute flight deals from Chicago to Jamaica. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jamaica. Data last updated October 30, 2026 and is based on user searches.
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.
Sat 10/313:45 pm -
2 stops21h 05m
Tue 11/31:50 pm -
1 stop20h 33m
Deal found 10/26![Air Canada logo]()
$468
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 10/317:15 am -
1 stop7h 13m
Tue 11/31:50 pm -
1 stop27h 54m
Deal found 10/27![Multiple Airlines logo]()
$469
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 11/126:42 pm -
1 stop19h 26m
Mon 11/232:01 pm -
1 stop23h 20m
Deal found 10/27![Frontier logo]()
$477
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:45 am -
2 stops27h 40m
Mon 11/236:20 pm -
2 stops25h 10m
Deal found 10/27![Air Canada logo]()
$478
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:58 pm -
2 stops18h 27m
Tue 11/241:50 pm -
1 stop20h 33m
Deal found 10/27![Air Canada logo]()
$465
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.
Sat 11/145:58 pm -
2 stops18h 27m
Thu 11/191:50 pm -
2 stops19h 10m
Deal found 10/26![Air Canada logo]()
$470
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.
Mon 11/166:08 am -
1 stop8h 00m
Mon 11/232:01 pm -
1 stop19h 13m
Deal found 10/28![Frontier logo]()
$469
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.
Thu 11/196:42 pm -
1 stop17h 14m
Sun 11/222:01 pm -
1 stop19h 13m
Deal found 10/28![Frontier logo]()
$472
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:50 pm -
1 stop16h 06m
Mon 11/236:20 pm -
1 stop16h 24m
Deal found 10/27![Multiple Airlines logo]()
$474
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:49 am -
1 stop28h 07m
Wed 11/251:50 pm -
2 stops19h 10m
Deal found 10/28![Multiple Airlines logo]()
$476
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:49 am -
1 stop28h 07m
Wed 12/26:20 pm -
1 stop26h 38m
Deal found 10/25![Multiple Airlines logo]()
$482
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.
Mon 11/306:41 am -
1 stop6h 51m
Wed 12/211:05 am -
1 stop8h 20m
Deal found 10/28![American Airlines logo]()
$471
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 October 30, 2026.
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:05 am -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$184
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:08 am -
1 stop8h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$184
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 11/147:15 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$189
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 11/168:45 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Air Canada logo]()
$196
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.
Thu 11/267:49 am -
1 stop28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$202
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 11/278:40 pm -
1 stop19h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Air Canada logo]()
$213
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.
Mon 12/285:58 am -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$222
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:30 pm -
2 stops19h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Air Canada logo]()
$224
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.
Mon 11/169:40 am -
Nonstop4h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$227
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.
Tue 12/296:25 am -
1 stop13h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$231
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.
Mon 11/235:05 am -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$231
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/227:00 am -
1 stop6h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![JetBlue logo]()
$233
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $465 (Air Canada) |
One-way from | $184 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $522 |
Good round-trip deal | $626 or less |
Good one-way deal | $268 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 October 30, 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 12/29
6:00 am-9:10 pm
1 stop14h 10m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$231
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 11/23
5:05 am-2:25 pm
1 stop8h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$231
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 11/15
7:00 am-2:57 pm
1 stop6h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sat 11/21
7:49 am-12:56 pm
1 stop28h 07m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
Quickest round-trip
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Fri 1/22
7:00 am-2:12 pm
1 stop6h 12m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/29
1:11 pm-1:44 pm
1 stop23h 33m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$253
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 3/22
6:00 am-1:39 pm
1 stop7h 39m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$257
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Wed 11/18
5:55 am-2:14 pm
1 stop7h 19m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$258
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 11/15
5:05 am-2:45 pm
2 stops8h 40m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$277
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/29
6:52 am-12:45 pm
2 stops28h 53m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
Showing 1-10 of 59 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-OCJ
ORD-KIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Jamaica
CHI-JM0
ORD-MBJ
MDW-MBJ
ORD-OCJ
ORD-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 $475). Flying from Chicago to Jamaica in December is currently the most expensive (average of $696). 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 58 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 October 30, 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.
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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.
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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 October 30, 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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$602 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$552 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$301 | Average$575 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$614 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$322 | Average$625 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |