$185+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Aug 31 — Sep 71
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 August 1, 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 August 1, 2026.
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:45 pm
ORD
- MBJ
2 stops20h 05m
Air Canada
Sun 11/12:20 pm
MBJ
- ORD
1 stop25h 32m
Air Canada
Deal found 7/31![Air Canada logo]()
$419
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/2411:05 am
ORD
- MBJ
1 stop25h 20m
Air Canada
Thu 10/2912:50 pm
MBJ
- ORD
2 stops19h 10m
Air Canada
Deal found 7/31![Air Canada logo]()
$420
This Air Canada deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:50 pm
ORD
- MBJ
1 stop19h 30m
Air Canada
Mon 11/96:20 pm
MBJ
- ORD
1 stop16h 03m
Air Canada
Deal found 8/1![Air Canada logo]()
$421
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Sun 11/88:50 pm
ORD
- MBJ
1 stop15h 00m
Air Canada
Sat 11/146:20 pm
MBJ
- ORD
1 stop16h 03m
Air Canada
Deal found 7/31![Air Canada logo]()
$422
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:45 pm
ORD
- MBJ
2 stops20h 05m
Air Canada
Mon 11/26:20 pm
MBJ
- ORD
1 stop16h 03m
Air Canada
Deal found 7/31![Air Canada logo]()
$424
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/242:01 pm
ORD
- MBJ
1 stop22h 24m
Air Canada
Wed 10/2812:50 pm
MBJ
- ORD
1 stop20h 33m
Air Canada
Deal found 7/31![Air Canada logo]()
$425
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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
ORD
- MBJ
1 stop21h 40m
Air Canada
Mon 11/21:50 pm
MBJ
- ORD
1 stop20h 33m
Air Canada
Deal found 7/31![Air Canada logo]()
$426
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/318:40 am
ORD
- MBJ
Nonstop4h 08m
United Airlines
Sat 11/72:54 pm
MBJ
- ORD
Nonstop4h 26m
United Airlines
Deal found 7/31![United Airlines logo]()
$428
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Sun 10/259:05 pm
ORD
- MBJ
1 stop19h 15m
Air Canada
Mon 11/26:20 pm
MBJ
- ORD
1 stop14h 34m
Air Canada
Deal found 7/31![Air Canada logo]()
$430
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/269:21 pm
ORD
- MBJ
1 stop14h 29m
Air Canada
Sat 10/3112:50 pm
MBJ
- ORD
1 stop9h 13m
Air Canada
Deal found 7/31![Air Canada logo]()
$431
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 8/248:49 pm
ORD
- MBJ
1 stop17h 34m
American Airlines
Thu 8/272:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Deal found 7/30![American Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 7/29. 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.
Sun 11/156:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Sat 11/214:00 pm
MBJ
- MDW
1 stop17h 50m
Delta
Deal found 7/29![Delta logo]()
$442
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 August 1, 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 August 1, 2026.
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 11/136:00 am
ORD
- MBJ
1 stop7h 14m
United Airlines
Sun 11/153:45 pm
MBJ
- ORD
1 stop10h 00m
United Airlines
Deal found 7/29![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 7/29. 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.
Sun 12/66:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Thu 12/103:40 pm
MBJ
- MDW
1 stop8h 16m
Delta
Deal found 7/29![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Tue 9/2912:55 pm
MBJ
- MDW
1 stop8h 30m
Southwest
Deal found 7/31![Southwest logo]()
$442
This Copa Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 8/223:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Fri 8/2811:23 am
MBJ
- ORD
1 stop13h 39m
Copa Airlines
Deal found 7/27![Copa Airlines logo]()
$474
This JetBlue deal was found by Cheapflights users on 7/29. 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.
Sat 10/246:30 am
ORD
- KIN
1 stop9h 34m
JetBlue
Thu 11/122:55 pm
KIN
- ORD
1 stop9h 49m
JetBlue
Deal found 7/29![JetBlue logo]()
$533
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/218:54 am
ORD
- KIN
2 stops10h 48m
American Airlines
Mon 8/245:24 pm
KIN
- ORD
1 stop16h 36m
American Airlines
Deal found 7/31![American Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 1/168:55 am
ORD
- MBJ
1 stop6h 29m
United Airlines
Sat 1/233:20 pm
MBJ
- ORD
1 stop8h 16m
United Airlines
Deal found 7/27![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 11/116:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Tue 11/243:40 pm
MBJ
- MDW
1 stop8h 16m
Delta
Deal found 7/29![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 7/30. 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.
Sat 8/295:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Wed 9/21:55 pm
MBJ
- MDW
1 stop6h 50m
Southwest
Deal found 7/30![Southwest logo]()
$442
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/199:35 pm
ORD
- MBJ
1 stop14h 08m
United Airlines
Wed 9/2312:52 pm
MBJ
- ORD
1 stop9h 23m
United Airlines
Deal found 7/31![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 12/46:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Wed 12/93:40 pm
MBJ
- MDW
1 stop8h 16m
Delta
Deal found 7/29![Delta logo]()
$442
This Copa Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/23:20 pm
ORD
- KIN
1 stop22h 31m
Copa Airlines
Wed 9/92:57 pm
KIN
- ORD
1 stop10h 05m
Copa Airlines
Deal found 7/31![Copa Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:30 am
ORD
- MBJ
1 stop8h 09m
United Airlines
Sun 11/83:45 pm
MBJ
- ORD
1 stop10h 00m
United Airlines
Deal found 7/30![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/255:29 pm
ORD
- MBJ
2 stops19h 31m
Delta
Tue 10/271:16 pm
MBJ
- ORD
1 stop7h 36m
Delta
Deal found 7/31![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Sat 9/121:50 pm
MBJ
- MDW
1 stop7h 10m
Southwest
Deal found 7/31![Southwest logo]()
$512
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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
- KIN
1 stop6h 45m
JetBlue
Mon 9/213:05 pm
KIN
- ORD
1 stop8h 03m
JetBlue
Deal found 7/31![JetBlue logo]()
$573
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:40 am
ORD
- MBJ
1 stop8h 54m
Delta
Thu 8/274:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Deal found 7/30![Delta logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/143:20 pm
ORD
- KIN
1 stop22h 34m
Copa Airlines
Mon 9/212:57 pm
KIN
- ORD
1 stop10h 05m
Copa Airlines
Deal found 7/31![Copa Airlines logo]()
$546
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/117:50 pm
MDW
- MBJ
2 stops16h 35m
Southwest
Fri 9/182:15 pm
MBJ
- MDW
2 stops8h 10m
Southwest
Deal found 7/28![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/283:40 pm
ORD
- MBJ
2 stops19h 50m
Delta
Fri 10/304:44 pm
MBJ
- ORD
1 stop7h 08m
Delta
Deal found 7/31![Delta logo]()
$447
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/46:45 am
ORD
- KIN
2 stops9h 39m
American Airlines
Sun 9/135:08 pm
KIN
- ORD
2 stops16h 00m
American Airlines
Deal found 8/1![American Airlines logo]()
$672
This Southwest deal was found by Cheapflights users on 7/27. 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 8/287:55 pm
MDW
- MBJ
2 stops15h 25m
Southwest
Fri 9/42:15 pm
MBJ
- MDW
1 stop8h 30m
Southwest
Deal found 7/27![Southwest logo]()
$532
This Delta deal was found by Cheapflights users on 7/28. 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 10/246:30 am
ORD
- MBJ
1 stop6h 30m
Delta
Wed 10/281:16 pm
MBJ
- ORD
2 stops18h 25m
Delta
Deal found 7/28![Delta logo]()
$447
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am
ORD
- KIN
1 stop6h 45m
JetBlue
Fri 9/183:05 pm
KIN
- ORD
1 stop8h 03m
JetBlue
Deal found 7/28![JetBlue logo]()
$695
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/257:30 pm
ORD
- MBJ
2 stops19h 59m
Delta
Sat 10/311:16 pm
MBJ
- ORD
1 stop7h 36m
Delta
Deal found 7/31![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 12/49:53 am
ORD
- MBJ
1 stop5h 42m
Delta
Wed 12/96:00 pm
MBJ
- ORD
2 stops14h 46m
Delta
Deal found 7/29![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 11/116:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Mon 11/236:00 pm
MBJ
- MDW
2 stops16h 42m
Delta
Deal found 7/29![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 7/28. 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 9/128:05 am
ORD
- MBJ
1 stop7h 30m
Delta
Sat 9/191:14 pm
MBJ
- ORD
1 stop7h 42m
Delta
Deal found 7/28![Delta logo]()
$480
This Delta deal was found by Cheapflights users on 7/27. 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.
Thu 10/110:48 am
MDW
- KIN
1 stop9h 22m
Delta
Mon 10/59:10 am
KIN
- MDW
1 stop7h 05m
Delta
Deal found 7/27![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 7/29. 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 10/2411:33 am
MDW
- KIN
1 stop8h 42m
Delta
Fri 11/139:00 am
KIN
- MDW
1 stop8h 14m
Delta
Deal found 7/29![Delta logo]()
$564
Last-minute flights from Chicago to JamaicaDiscover last-minute flight deals from Chicago to Jamaica. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jamaica. Data last updated August 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 8/145:00 am
ORD
- MBJ
1 stop9h 23m
American Airlines
Thu 8/2012:47 pm
MBJ
- ORD
1 stop19h 58m
American Airlines
Deal found 7/30![American Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sun 8/165:00 am
ORD
- KIN
1 stop14h 42m
American Airlines
Sat 8/222:00 pm
KIN
- ORD
1 stop17h 34m
American Airlines
Deal found 7/29![American Airlines logo]()
$468
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 8/218:37 am
ORD
- KIN
1 stop8h 05m
American Airlines
Sun 8/232:00 pm
KIN
- ORD
1 stop9h 30m
American Airlines
Deal found 7/29![American Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:42 pm
MDW
- MBJ
2 stops20h 52m
Delta
Thu 8/274:59 pm
MBJ
- MDW
2 stops19h 40m
Delta
Deal found 7/30![Delta logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 8/223:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Fri 8/2811:23 am
MBJ
- ORD
1 stop13h 39m
Copa Airlines
Deal found 7/29![Copa Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 8/228:49 pm
ORD
- MBJ
1 stop17h 34m
American Airlines
Fri 8/282:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Deal found 7/27![American Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:18 pm
ORD
- MBJ
2 stops22h 16m
Delta
Sat 8/294:59 pm
MBJ
- ORD
1 stop6h 58m
Delta
Deal found 7/30![Delta logo]()
$485
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 8/248:49 pm
ORD
- MBJ
1 stop17h 34m
American Airlines
Thu 8/272:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Deal found 7/30![American Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 7/29. 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.
Mon 8/246:40 am
ORD
- MBJ
1 stop8h 54m
Delta
Thu 8/274:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Deal found 7/29![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:30 am
ORD
- MBJ
1 stop10h 04m
Delta
Sat 8/294:59 pm
MBJ
- ORD
1 stop6h 58m
Delta
Deal found 7/30![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 7/30. 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.
Sat 8/295:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Wed 9/21:55 pm
MBJ
- MDW
1 stop6h 50m
Southwest
Deal found 7/30![Southwest logo]()
$442
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:11 am
MDW
- MBJ
1 stop9h 23m
Delta
Wed 9/21:09 pm
MBJ
- MDW
1 stop9h 27m
Delta
Deal found 7/30![Delta logo]()
$480
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 August 1, 2026.
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Travelocity deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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.
Sat 10/311:55 pm
ORD
- MBJ
1 stop23h 30m
Air Canada
Deal found 8/1![Air Canada logo]()
$185
This Travelocity deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/313:40 pm
ORD
- KIN
2 stops46h 15m
Air Canada
Deal found 7/31![Air Canada logo]()
$185
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/225:05 am
ORD
- KIN
2 stops7h 54m
American Airlines
Deal found 7/28![American Airlines logo]()
$189
This Air Canada deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:05 pm
ORD
- MBJ
1 stop14h 45m
Air Canada
Deal found 8/1![Air Canada logo]()
$190
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 1/228:05 am
ORD
- MBJ
Nonstop4h 14m
American Airlines
Deal found 7/30![American Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 9/126:00 am
ORD
- MBJ
1 stop10h 16m
American Airlines
Deal found 7/29![American Airlines logo]()
$194
This Air Canada deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:05 pm
ORD
- MBJ
1 stop14h 45m
Air Canada
Deal found 8/1![Air Canada logo]()
$195
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 9/114:35 pm
ORD
- KIN
1 stop19h 29m
American Airlines
Deal found 7/28![American Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:05 am
ORD
- MBJ
1 stop7h 24m
Delta
Deal found 7/30![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 7/29. 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 9/295:11 pm
MDW
- MBJ
2 stops18h 22m
Delta
Deal found 7/29![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/30. 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 9/135:25 am
MDW
- MBJ
1 stop6h 20m
Southwest
Deal found 7/30![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 7/28. 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.
Sun 9/275:00 am
MDW
- MBJ
1 stop9h 25m
Southwest
Deal found 7/28![Southwest logo]()
$200
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 August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $419 (Air Canada) |
One-way from | $185 (Travelocity) |
Popular in | December |
Cheapest in | September |
Average price | $532 |
Good round-trip deal | $547 or less |
Good one-way deal | $196 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 August 1, 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
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 11/13
6:00 am-2:14 pm
1 stop7h 14m
Montego Bay Sangster Intl
Sun 11/15
3:45 pm-12:45 am
1 stop10h 00m
$442
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 12/6
6:00 am-4:35 pm
1 stop9h 35m
Montego Bay Sangster Intl
Thu 12/10
3:40 pm-10:56 pm
1 stop8h 16m
$442
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 9/22
6:30 am-12:55 pm
1 stop6h 25m
Montego Bay Sangster Intl
Tue 9/29
12:55 pm-9:25 pm
1 stop8h 30m
$442
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 1/16
8:55 am-4:24 pm
1 stop6h 29m
Montego Bay Sangster Intl
Sat 1/23
3:20 pm-10:36 pm
1 stop8h 16m
$442
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 11/11
6:00 am-4:35 pm
1 stop9h 35m
Montego Bay Sangster Intl
Tue 11/24
3:40 pm-10:56 pm
1 stop8h 16m
$442
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 8/29
5:55 am-12:25 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 9/2
1:55 pm-8:45 pm
1 stop6h 50m
$442
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 9/19
9:35 pm-11:43 am
1 stop14h 08m
Montego Bay Sangster Intl
Wed 9/23
12:52 pm-10:15 pm
1 stop9h 23m
$442
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 12/4
6:00 am-4:35 pm
1 stop9h 35m
Montego Bay Sangster Intl
Wed 12/9
3:40 pm-10:56 pm
1 stop8h 16m
$442
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 11/1
5:30 am-2:39 pm
1 stop8h 09m
Montego Bay Sangster Intl
Sun 11/8
3:45 pm-12:45 am
1 stop10h 00m
$442
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 10/25
5:29 pm-1:00 pm
2 stops19h 31m
Montego Bay Sangster Intl
Tue 10/27
1:16 pm-8:52 pm
1 stop7h 36m
$447
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-KIN
ORD-MBJ
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-KIN
ORD-MBJ
MDW-MBJ
MDW-KIN
What is the cheapest month to book a flight from Chicago to Jamaica?
Currently, April is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $480). Flying from Chicago to Jamaica in December is currently the most expensive (average of $669). 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 August 1, 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.
Weekly flight availability from Chicago to Jamaica
Explore weekly flight availability from Chicago to Jamaica. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 1, 2026.
The most flights from CHI to JM0 are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from Chicago to Jamaica?
Booking 87 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 August 1, 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
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 August 1, 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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$686 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$605 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$297 | Average$510 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$297 | Average$524 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$663 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |