$158+ Cheap flights from Chicago (CHI) to Jamaica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Jul 17 — Jul 241
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
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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 June 17, 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 June 17, 2026.
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:00 am
ORD
- MBJ
1 stop10h 33m
JetBlue
Mon 8/3112:55 pm
MBJ
- ORD
1 stop10h 49m
JetBlue
Deal found 6/15![JetBlue logo]()
$355
This Cheapflightsfares deal was found by Cheapflights users on 6/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
ORD
- MBJ
1 stop10h 33m
JetBlue
Tue 8/2512:55 pm
MBJ
- ORD
1 stop10h 49m
JetBlue
Deal found 6/13![JetBlue logo]()
$369
This JetBlue deal was found by Cheapflights users on 6/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am
ORD
- MBJ
1 stop6h 54m
JetBlue
Wed 11/112:00 pm
MBJ
- ORD
1 stop10h 44m
JetBlue
Deal found 6/15![JetBlue logo]()
$374
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:00 am
ORD
- MBJ
1 stop6h 54m
JetBlue
Wed 11/113:59 pm
MBJ
- ORD
1 stop8h 45m
JetBlue
Deal found 6/15![JetBlue logo]()
$382
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Tue 11/37:00 am
ORD
- MBJ
1 stop6h 54m
JetBlue
Thu 11/123:59 pm
MBJ
- ORD
1 stop8h 45m
JetBlue
Deal found 6/16![JetBlue logo]()
$384
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:00 am
ORD
- MBJ
1 stop7h 47m
JetBlue
Tue 12/82:45 pm
MBJ
- ORD
1 stop9h 59m
JetBlue
Deal found 6/17![JetBlue logo]()
$391
This FlightHub deal was found by Cheapflights users on 6/14. 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.
Sat 10/317:00 am
ORD
- MBJ
1 stop6h 48m
JetBlue
Tue 11/32:00 pm
MBJ
- ORD
1 stop10h 44m
JetBlue
Deal found 6/14![JetBlue logo]()
$399
This FlightHub deal was found by Cheapflights users on 6/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
ORD
- MBJ
1 stop7h 47m
JetBlue
Sat 12/121:00 pm
MBJ
- ORD
1 stop11h 44m
JetBlue
Deal found 6/16![JetBlue logo]()
$409
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 10/207:00 am
ORD
- KIN
1 stop5h 43m
JetBlue
Wed 10/283:55 pm
KIN
- ORD
1 stop7h 49m
JetBlue
Deal found 6/15![JetBlue logo]()
$451
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Wed 8/121:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/16![Frontier logo]()
$452
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:00 am
ORD
- KIN
1 stop14h 53m
American Airlines
Thu 6/256:22 am
KIN
- ORD
1 stop15h 38m
American Airlines
Deal found 6/14![American Airlines logo]()
$456
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Fri 8/216:00 am
ORD
- KIN
1 stop10h 42m
American Airlines
Sun 8/236:05 am
KIN
- ORD
1 stop17h 25m
American Airlines
Deal found 6/13![American Airlines logo]()
$461
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 June 17, 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 June 17, 2026.
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am
ORD
- KIN
1 stop10h 06m
JetBlue
Wed 9/21:56 pm
KIN
- ORD
1 stop9h 48m
JetBlue
Deal found 6/14![JetBlue logo]()
$456
This Copa Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 7/188:02 am
ORD
- MBJ
1 stop26h 09m
Copa Airlines
Fri 7/2411:16 am
MBJ
- ORD
1 stop12h 45m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:54 am
MDW
- KIN
1 stop9h 19m
Delta
Sun 9/139:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 6/13![Delta logo]()
$524
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Tue 8/44:12 pm
MBJ
- ORD
1 stop7h 19m
United Airlines
Deal found 6/12![United Airlines logo]()
$566
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/95:00 am
MDW
- MBJ
2 stops8h 30m
Southwest
Thu 8/1312:15 pm
MBJ
- MDW
2 stops10h 05m
Southwest
Deal found 6/13![Southwest logo]()
$573
This CheapOair deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:58 pm
ORD
- MBJ
1 stop12h 14m
Multiple Airlines
Wed 7/2912:30 pm
MBJ
- ORD
2 stops30h 14m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$588
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
ORD
- KIN
1 stop10h 18m
JetBlue
Tue 7/2812:08 pm
KIN
- ORD
1 stop11h 36m
JetBlue
Deal found 6/17![JetBlue logo]()
$466
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- KIN
1 stop14h 08m
Delta
Tue 8/259:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 6/16![Delta logo]()
$524
This Copa Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 7/258:02 am
ORD
- MBJ
1 stop27h 13m
Copa Airlines
Tue 7/2812:22 pm
MBJ
- ORD
1 stop25h 35m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$560
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:54 am
ORD
- KIN
1 stop10h 19m
Delta
Sun 9/139:00 am
KIN
- ORD
1 stop11h 27m
Delta
Deal found 6/15![Delta logo]()
$524
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Fri 7/172:35 pm
ORD
- KIN
1 stop9h 02m
JetBlue
Fri 7/2412:08 pm
KIN
- ORD
1 stop11h 36m
JetBlue
Deal found 6/16![JetBlue logo]()
$532
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/118:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 7/181:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 6/15![United Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:10 am
MDW
- MBJ
1 stop8h 10m
Southwest
Sun 8/23:35 pm
MBJ
- MDW
2 stops8h 50m
Southwest
Deal found 6/12![Southwest logo]()
$615
This Copa Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/133:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Fri 7/1712:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Deal found 6/14![Copa Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 6/14. 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 7/305:30 am
ORD
- KIN
1 stop14h 34m
Delta
Wed 8/59:13 am
KIN
- ORD
1 stop11h 42m
Delta
Deal found 6/14![Delta logo]()
$524
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:55 am
MDW
- MBJ
2 stops7h 20m
Southwest
Tue 9/81:55 pm
MBJ
- MDW
1 stop6h 50m
Southwest
Deal found 6/12![Southwest logo]()
$615
This Copa Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/181:20 am
ORD
- MBJ
1 stop8h 51m
Copa Airlines
Sun 7/2611:16 am
MBJ
- ORD
1 stop26h 41m
Copa Airlines
Deal found 6/13![Copa Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 6/14. 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.
Sun 8/166:40 am
ORD
- MBJ
1 stop6h 21m
Delta
Thu 8/204:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Deal found 6/14![Delta logo]()
$533
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 pm
MDW
- MBJ
2 stops16h 35m
Southwest
Mon 9/1412:15 pm
MBJ
- MDW
2 stops10h 05m
Southwest
Deal found 6/12![Southwest logo]()
$617
This Copa Airlines deal was found by Cheapflights users on 6/17. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:21 pm
ORD
- KIN
1 stop22h 33m
Copa Airlines
Wed 7/222:56 pm
KIN
- ORD
1 stop23h 01m
Copa Airlines
Deal found 6/17![Copa Airlines logo]()
$576
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:40 am
ORD
- MBJ
1 stop8h 54m
Delta
Tue 8/181:09 pm
MBJ
- ORD
1 stop7h 46m
Delta
Deal found 6/13![Delta logo]()
$570
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:55 pm
MDW
- MBJ
2 stops15h 25m
Southwest
Mon 8/1712:15 pm
MBJ
- MDW
2 stops9h 40m
Southwest
Deal found 6/15![Southwest logo]()
$640
This Copa Airlines deal was found by Cheapflights users on 6/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Tue 8/1112:22 pm
MBJ
- ORD
1 stop12h 40m
Copa Airlines
Deal found 6/15![Copa Airlines logo]()
$595
This Delta deal was found by Cheapflights users on 6/14. 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 7/306:35 am
ORD
- KIN
1 stop13h 29m
Delta
Mon 8/39:13 am
KIN
- ORD
1 stop14h 44m
Delta
Deal found 6/14![Delta logo]()
$580
This Southwest deal was found by Cheapflights users on 6/13. 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.
Fri 8/215:55 am
MDW
- MBJ
2 stops7h 20m
Southwest
Tue 8/2512:55 pm
MBJ
- MDW
2 stops9h 25m
Southwest
Deal found 6/13![Southwest logo]()
$662
This Delta deal was found by Cheapflights users on 6/14. 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.
Tue 7/286:58 pm
MDW
- KIN
2 stops25h 05m
Delta
Thu 8/69:13 am
KIN
- MDW
2 stops24h 04m
Delta
Deal found 6/14![Delta logo]()
$585
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:35 pm
MDW
- MBJ
2 stops16h 20m
Southwest
Thu 7/92:20 pm
MBJ
- MDW
2 stops9h 50m
Southwest
Deal found 6/12![Southwest logo]()
$662
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:10 pm
MDW
- MBJ
2 stops18h 15m
Southwest
Mon 8/311:45 am
MBJ
- MDW
2 stops9h 30m
Southwest
Deal found 6/12![Southwest logo]()
$677
This Delta deal was found by Cheapflights users on 6/14. 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.
Sun 8/95:30 am
ORD
- MBJ
1 stop10h 04m
Delta
Thu 8/134:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Deal found 6/14![Delta logo]()
$620
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:10 am
MDW
- MBJ
2 stops8h 45m
Southwest
Sun 7/263:35 pm
MBJ
- MDW
2 stops8h 50m
Southwest
Deal found 6/13![Southwest logo]()
$695
Last-minute flights from Chicago to JamaicaDiscover last-minute flight deals from Chicago to Jamaica. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jamaica. Data last updated June 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 6/196:10 am
ORD
- KIN
1 stop13h 43m
American Airlines
Thu 6/255:10 pm
KIN
- ORD
1 stop7h 09m
American Airlines
Deal found 6/15![American Airlines logo]()
$468
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Fri 6/195:00 am
ORD
- KIN
1 stop14h 53m
American Airlines
Sun 6/216:22 am
KIN
- ORD
1 stop17h 08m
American Airlines
Deal found 6/16![American Airlines logo]()
$471
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:00 am
ORD
- KIN
1 stop14h 53m
American Airlines
Thu 6/256:22 am
KIN
- ORD
1 stop15h 38m
American Airlines
Deal found 6/14![American Airlines logo]()
$456
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Mon 6/296:10 am
ORD
- KIN
1 stop9h 58m
American Airlines
Fri 7/105:03 pm
KIN
- ORD
1 stop16h 05m
American Airlines
Deal found 6/13![American Airlines logo]()
$481
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Thu 7/211:00 am
ORD
- KIN
2 stops9h 09m
American Airlines
Sun 7/55:03 pm
KIN
- ORD
1 stop16h 05m
American Airlines
Deal found 6/15![American Airlines logo]()
$491
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:30 am
ORD
- KIN
1 stop11h 42m
American Airlines
Mon 7/136:20 am
KIN
- ORD
1 stop13h 33m
American Airlines
Deal found 6/17![American Airlines logo]()
$466
This CheapOair deal was found by Cheapflights users on 6/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop21h 35m
Frontier
Deal found 6/17![Frontier logo]()
$491
This Copa Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 7/188:02 am
ORD
- MBJ
1 stop26h 09m
Copa Airlines
Fri 7/2411:16 am
MBJ
- ORD
1 stop12h 45m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$468
This Travelocity deal was found by Cheapflights users on 6/15. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:58 pm
ORD
- MBJ
1 stop12h 14m
Multiple Airlines
Sat 8/2212:55 pm
MBJ
- ORD
1 stop10h 49m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$460
This Expedia deal was found by Cheapflights users on 6/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Mon 8/31:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/12![Frontier logo]()
$472
This Trip.com deal was found by Cheapflights users on 6/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Thu 7/301:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/17![Frontier logo]()
$486
This Expedia deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:58 pm
ORD
- MBJ
1 stop12h 14m
Multiple Airlines
Wed 9/212:55 pm
MBJ
- ORD
1 stop10h 49m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$437
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 June 17, 2026.
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated June 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- MBJ
1 stop10h 33m
JetBlue
Deal found 6/13![JetBlue logo]()
$158
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
- MBJ
1 stop10h 33m
JetBlue
Deal found 6/17![JetBlue logo]()
$159
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
ORD
- MBJ
1 stop10h 33m
JetBlue
Deal found 6/14![JetBlue logo]()
$163
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Mon 8/107:00 am
ORD
- MBJ
1 stop10h 33m
JetBlue
Deal found 6/16![JetBlue logo]()
$168
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:35 pm
ORD
- KIN
1 stop9h 02m
JetBlue
Deal found 6/15![JetBlue logo]()
$175
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:00 am
ORD
- KIN
1 stop10h 18m
JetBlue
Deal found 6/15![JetBlue logo]()
$179
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am
ORD
- MBJ
1 stop6h 03m
JetBlue
Deal found 6/14![JetBlue logo]()
$181
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 7/85:00 am
ORD
- KIN
1 stop15h 12m
American Airlines
Deal found 6/15![American Airlines logo]()
$183
This Expedia deal was found by Cheapflights users on 6/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am
ORD
- KIN
1 stop5h 46m
JetBlue
Deal found 6/15![JetBlue logo]()
$184
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am
ORD
- MBJ
1 stop6h 03m
JetBlue
Deal found 6/17![JetBlue logo]()
$186
This FlightHub deal was found by Cheapflights users on 6/14. 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.
Mon 7/137:00 am
ORD
- KIN
1 stop10h 18m
JetBlue
Deal found 6/14![JetBlue logo]()
$187
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:59 pm
ORD
- KIN
1 stop18h 00m
American Airlines
Deal found 6/17![American Airlines logo]()
$194
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 June 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $355 (Super.com) |
One-way from | $158 (Cheapflightsfares) |
Popular in | March |
Cheapest in | September |
Average price | $583 |
Good round-trip deal | $450 or less |
Good one-way deal | $148 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 2,558,603 searches. Data last updated June 17, 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
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Mon 8/31
7:00 am-5:06 pm
1 stop10h 06m
Kingston Norman Manley
Wed 9/2
1:56 pm-11:44 pm
1 stop9h 48m
$456
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Wed 7/22
7:00 am-5:18 pm
1 stop10h 18m
Kingston Norman Manley
Tue 7/28
12:08 pm-11:44 pm
1 stop11h 36m
$466
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 7/18
8:02 am-10:11 am
1 stop26h 09m
Montego Bay Sangster Intl
Fri 7/24
11:16 am-12:01 am
1 stop12h 45m
$468
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 9/4
10:54 am-8:13 pm
1 stop9h 19m
Kingston Norman Manley
Sun 9/13
9:00 am-9:46 pm
1 stop12h 46m
$524
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Sat 8/15
6:05 am-8:13 pm
1 stop14h 08m
Kingston Norman Manley
Tue 8/25
9:13 am-10:36 pm
1 stop13h 23m
$524
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Fri 9/4
9:54 am-8:13 pm
1 stop10h 19m
Kingston Norman Manley
Sun 9/13
9:00 am-8:27 pm
1 stop11h 27m
$524
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Thu 7/30
5:30 am-8:04 pm
1 stop14h 34m
Kingston Norman Manley
Wed 8/5
9:13 am-8:55 pm
1 stop11h 42m
$524
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Fri 7/17
2:35 pm-11:37 pm
1 stop9h 02m
Kingston Norman Manley
Fri 7/24
12:08 pm-11:44 pm
1 stop11h 36m
$532
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 8/16
6:40 am-1:01 pm
1 stop6h 21m
Montego Bay Sangster Intl
Thu 8/20
4:59 pm-7:56 am
2 stops14h 57m
$533
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 7/25
8:02 am-11:15 am
1 stop27h 13m
Montego Bay Sangster Intl
Tue 7/28
12:22 pm-1:57 pm
1 stop25h 35m
$560
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
ORD-MBJ
ORD-KIN
MDW-MBJ
MDW-KIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Jamaica
CHI-JM0
ORD-MBJ
ORD-KIN
MDW-MBJ
MDW-KIN
What is the cheapest month to book a flight from Chicago to Jamaica?
Currently, December is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $84). Flying from Chicago to Jamaica in September is currently the most expensive (average of $238). 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.
What is the cheapest time of day to fly from CHI to JM?
Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 17, 2026.
When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 June 17, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Jamaica
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jamaica by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Jamaica by cabin class
Find flights from Chicago to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Jamaica flights
Browse other Chicago and Jamaica flight options. Last updated on June 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$715 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$599 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$297 | Average$510 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$297 | Average$520 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$645 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |