$118+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Jun 2 — Jun 91
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 May 3, 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 May 3, 2026.
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/129:15 am
ORD
- MBJ
Nonstop4h 16m
American Airlines
Thu 7/162:31 pm
MBJ
- ORD
Nonstop4h 51m
American Airlines
Deal found 4/29![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 11/37:10 am
ORD
- MBJ
1 stop6h 40m
American Airlines
Tue 11/102:19 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 4/28![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 4/28. 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 12/138:10 am
ORD
- MBJ
Nonstop4h 10m
American Airlines
Sun 12/204:27 pm
MBJ
- ORD
Nonstop4h 37m
American Airlines
Deal found 4/28![American Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 4/28. 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 11/76:35 pm
ORD
- MBJ
1 stop17h 19m
American Airlines
Sun 11/153:14 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 4/28![American Airlines logo]()
$327
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$328
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 5/118:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Fri 5/1510:17 am
MBJ
- ORD
1 stop13h 37m
American Airlines
Deal found 4/29![American Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/35:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Thu 5/72:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 4/29![United Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 4/298:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Sat 5/210:13 am
MBJ
- ORD
1 stop7h 45m
American Airlines
Deal found 4/29![American Airlines logo]()
$333
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 6/21:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$338
This American Airlines deal was found by Cheapflights users on 4/28. 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 9/196:35 pm
ORD
- MBJ
1 stop14h 35m
American Airlines
Tue 9/293:15 pm
MBJ
- ORD
1 stop17h 30m
American Airlines
Deal found 4/28![American Airlines logo]()
$341
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$348
This Frontier deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/186:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Thu 5/211:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/3![Frontier logo]()
$358
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 May 3, 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 May 3, 2026.
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 7/246:00 am
ORD
- MBJ
1 stop9h 10m
United Airlines
Tue 7/284:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/30![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/29. 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 7/226:00 am
MDW
- MBJ
1 stop8h 55m
Southwest
Wed 7/291:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/29![Southwest logo]()
$447
This Travelocity deal was found by Cheapflights users on 4/28. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:55 am
ORD
- KIN
1 stop24h 30m
Air Canada
Wed 6/103:05 pm
KIN
- ORD
1 stop17h 55m
Air Canada
Deal found 4/28![Air Canada logo]()
$528
This Copa Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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.
Tue 7/211:20 am
ORD
- KIN
1 stop12h 34m
Copa Airlines
Tue 7/282:56 pm
KIN
- ORD
1 stop13h 04m
Copa Airlines
Deal found 5/2![Copa Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:05 am
ORD
- KIN
1 stop12h 55m
Delta
Sat 5/309:00 am
KIN
- ORD
1 stop15h 03m
Delta
Deal found 5/1![Delta logo]()
$576
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 6/26:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Tue 6/94:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/28![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 7/248:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Wed 7/294:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/30![United Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 6/208:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Wed 6/244:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/29![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 4/29. 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.
Fri 7/247:00 am
MDW
- MBJ
1 stop7h 55m
Southwest
Wed 7/291:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/29![Southwest logo]()
$450
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/316:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sun 6/74:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 5/2![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 7/1410:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Sun 7/262:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/30![Southwest logo]()
$471
This Air Canada deal was found by Cheapflights users on 4/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/179:55 am
ORD
- KIN
1 stop24h 30m
Air Canada
Wed 6/243:05 pm
KIN
- ORD
2 stops27h 42m
Air Canada
Deal found 4/29![Air Canada logo]()
$568
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:30 am
ORD
- KIN
1 stop14h 00m
Delta
Mon 10/129:00 am
KIN
- ORD
1 stop12h 45m
Delta
Deal found 4/29![Delta logo]()
$576
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 7/2210:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Fri 7/311:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/28![Southwest logo]()
$481
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/156:00 am
ORD
- MBJ
1 stop9h 10m
United Airlines
Mon 5/184:12 pm
MBJ
- ORD
1 stop7h 32m
United Airlines
Deal found 5/2![United Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/239:22 am
MDW
- KIN
2 stops10h 38m
Delta
Sat 5/309:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 5/3![Delta logo]()
$581
This Southwest deal was found by Cheapflights users on 5/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:00 am
MDW
- MBJ
1 stop8h 15m
Southwest
Thu 8/2012:15 pm
MBJ
- MDW
2 stops10h 05m
Southwest
Deal found 5/1![Southwest logo]()
$485
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 5/305:30 am
ORD
- MBJ
1 stop9h 56m
United Airlines
Sat 6/64:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/29![United Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 10/286:00 am
ORD
- MBJ
1 stop7h 29m
United Airlines
Sun 11/12:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Deal found 4/29![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 4/29. 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 9/410:35 am
MDW
- KIN
1 stop9h 29m
Delta
Sun 9/139:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 4/29![Delta logo]()
$660
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/197:00 am
MDW
- MBJ
1 stop6h 55m
Southwest
Sun 5/2412:00 pm
MBJ
- MDW
2 stops10h 55m
Southwest
Deal found 5/2![Southwest logo]()
$550
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:53 pm
MDW
- KIN
1 stop7h 07m
Delta
Sun 5/319:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 5/1![Delta logo]()
$660
This United Airlines deal was found by Cheapflights users on 4/28. 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 7/186:30 am
ORD
- MBJ
1 stop8h 56m
United Airlines
Fri 7/244:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/28![United Airlines logo]()
$452
This Southwest deal was found by Cheapflights users on 4/29. 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.
Mon 7/2010:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Mon 7/271:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/29![Southwest logo]()
$576
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 10/141:05 pm
MDW
- KIN
1 stop6h 25m
Delta
Mon 10/199:00 am
KIN
- MDW
1 stop12h 45m
Delta
Deal found 4/30![Delta logo]()
$660
This United Airlines deal was found by Cheapflights users on 4/30. 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 7/125:30 am
ORD
- MBJ
1 stop9h 56m
United Airlines
Sat 7/184:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Deal found 4/30![United Airlines logo]()
$452
This Southwest deal was found by Cheapflights users on 4/30. 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.
Thu 9/107:50 pm
MDW
- MBJ
2 stops17h 50m
Southwest
Mon 9/142:15 pm
MBJ
- MDW
1 stop8h 25m
Southwest
Deal found 4/30![Southwest logo]()
$598
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/56:23 am
MDW
- KIN
1 stop13h 37m
Delta
Mon 6/89:00 am
KIN
- MDW
1 stop7h 16m
Delta
Deal found 5/2![Delta logo]()
$660
This Delta deal was found by Cheapflights users on 4/29. 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 9/41:15 pm
ORD
- KIN
1 stop6h 49m
Delta
Sun 9/139:00 am
KIN
- ORD
1 stop14h 57m
Delta
Deal found 4/29![Delta logo]()
$660
This Southwest deal was found by Cheapflights users on 5/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:05 am
MDW
- MBJ
1 stop7h 30m
Southwest
Sat 7/2511:55 am
MBJ
- MDW
1 stop6h 25m
Southwest
Deal found 5/1![Southwest logo]()
$610
Last-minute flights from Chicago to JamaicaDiscover last-minute flight deals from Chicago to Jamaica. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jamaica. Data last updated May 3, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/28:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Mon 5/44:12 pm
MBJ
- ORD
1 stop7h 32m
United Airlines
Deal found 4/28![United Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/39:56 pm
ORD
- MBJ
1 stop15h 34m
United Airlines
Sat 5/92:40 pm
MBJ
- ORD
1 stop8h 35m
United Airlines
Deal found 4/29![United Airlines logo]()
$332
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$328
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 5/78:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Thu 5/141:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/30![American Airlines logo]()
$338
This Priceline deal was found by Cheapflights users on 4/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$393
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 5/118:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Fri 5/1510:17 am
MBJ
- ORD
1 stop13h 37m
American Airlines
Deal found 4/29![American Airlines logo]()
$328
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$348
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 5/147:00 pm
ORD
- MBJ
1 stop20h 37m
American Airlines
Wed 5/201:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/30![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/156:41 pm
ORD
- MBJ
1 stop14h 32m
American Airlines
Thu 5/212:30 pm
MBJ
- ORD
Nonstop4h 45m
American Airlines
Deal found 4/30![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/185:00 am
ORD
- MBJ
1 stop8h 25m
American Airlines
Thu 5/212:30 pm
MBJ
- ORD
Nonstop4h 45m
American Airlines
Deal found 4/28![American Airlines logo]()
$322
This Frontier deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/186:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Thu 5/211:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/3![Frontier logo]()
$358
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 6/21:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$338
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 May 3, 2026.
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 5/1![Frontier logo]()
$118
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:50 am
ORD
- MBJ
1 stop29h 21m
Frontier
Deal found 4/29![Frontier logo]()
$135
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:19 pm
MDW
- MBJ
1 stop23h 52m
Frontier
Deal found 4/29![Frontier logo]()
$135
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/88:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 4/29![American Airlines logo]()
$138
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 8/269:10 am
ORD
- MBJ
Nonstop4h 07m
American Airlines
Deal found 4/28![American Airlines logo]()
$143
This FlightHub deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:05 am
ORD
- MBJ
1 stop7h 26m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$147
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 5/198:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 4/30![American Airlines logo]()
$148
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/287:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Deal found 5/3![Southwest logo]()
$148
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/189:02 pm
ORD
- MBJ
2 stops12h 08m
American Airlines
Deal found 4/30![American Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 4/28. 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 6/206:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 4/28![United Airlines logo]()
$161
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/30![Frontier logo]()
$162
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Thu 5/147:00 pm
ORD
- MBJ
1 stop20h 37m
American Airlines
Deal found 5/1![American Airlines logo]()
$167
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 May 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (American Airlines) |
One-way from | $118 (Priceline) |
Popular in | June |
Cheapest in | January |
Average price | $545 |
Good round-trip deal | $418 or less |
Good one-way deal | $138 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 May 3, 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 7/24
6:00 am-3:10 pm
1 stop9h 10m
Montego Bay Sangster Intl
Tue 7/28
4:12 pm-11:26 pm
1 stop7h 14m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 6/2
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Tue 6/9
4:12 pm-11:26 pm
1 stop7h 14m
$351
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 7/24
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 7/29
4:12 pm-11:26 pm
1 stop7h 14m
$352
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 6/20
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 6/24
4:12 pm-11:26 pm
1 stop7h 14m
$367
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 5/31
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sun 6/7
4:12 pm-11:26 pm
1 stop7h 14m
$373
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 5/15
6:00 am-3:10 pm
1 stop9h 10m
Montego Bay Sangster Intl
Mon 5/18
4:12 pm-11:44 pm
1 stop7h 32m
$406
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/30
5:30 am-3:26 pm
1 stop9h 56m
Montego Bay Sangster Intl
Sat 6/6
4:12 pm-11:26 pm
1 stop7h 14m
$426
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 10/28
6:00 am-1:29 pm
1 stop7h 29m
Montego Bay Sangster Intl
Sun 11/1
2:48 pm-6:16 pm
Nonstop4h 28m
$442
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 7/22
6:00 am-2:55 pm
1 stop8h 55m
Montego Bay Sangster Intl
Wed 7/29
1:50 pm-5:50 pm
Nonstop4h 00m
$447
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 7/24
7:00 am-2:55 pm
1 stop7h 55m
Montego Bay Sangster Intl
Wed 7/29
1:50 pm-5:50 pm
Nonstop4h 00m
$450
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.
MDW-MBJ
ORD-MBJ
ORD-KIN
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
MDW-MBJ
ORD-MBJ
ORD-KIN
MDW-KIN
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.
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 May is currently the most expensive (average of $277). 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 May 3, 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 May 3, 2026.
The most flights from CHI to JM0 are scheduled on a Saturday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
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 May 3, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 3, 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 May 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$457 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$144 | Average$675 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$537 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$302 | Average$526 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$323 | Average$651 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$468 | Average$653 | FlexibilityNo cancel fee | On-time63% |