$108+ Cheap flights from Illinois 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
May 30 — Jun 61
Round-trip
1 adult, Economy
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Cheapest flights from Illinois to JamaicaExplore the most affordable flight options available from Illinois to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
Explore the most affordable flight options available from Illinois to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Tue 7/71:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/26![Southwest logo]()
$318
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.
Tue 11/39:45 am
ORD
- MBJ
Nonstop4h 16m
American Airlines
Tue 11/102:19 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 4/29![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:05 am
ORD
- MBJ
1 stop7h 20m
American Airlines
Wed 5/131:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/26![American Airlines logo]()
$319
This Frontier deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:28 pm
ORD
- MBJ
1 stop19h 43m
Frontier
Wed 5/131:16 pm
MBJ
- ORD
1 stop18h 39m
Frontier
Deal found 4/26![Frontier logo]()
$320
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 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 4/28. 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 10/288:05 am
ORD
- MBJ
Nonstop4h 01m
American Airlines
Sun 11/12:19 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 4/28![American Airlines logo]()
$328
This Orbitz deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:55 am
ORD
- MBJ
1 stop29h 16m
Multiple Airlines
Thu 5/211:36 pm
MBJ
- ORD
1 stop9h 39m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Thu 4/302:40 pm
MBJ
- ORD
1 stop10h 46m
United Airlines
Deal found 4/25![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 American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:00 pm
ORD
- MBJ
1 stop19h 08m
American Airlines
Thu 6/252:30 pm
MBJ
- ORD
Nonstop4h 39m
American Airlines
Deal found 4/25![American Airlines logo]()
$336
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
Best flights from Illinois to JamaicaDiscover carefully curated flight deals from Illinois to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
Discover carefully curated flight deals from Illinois to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Thu 5/212:30 pm
MBJ
- ORD
Nonstop4h 45m
American Airlines
Deal found 4/25![American Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 4/25![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/27. 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.
Sat 7/1110:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 7/1512:35 pm
MBJ
- MDW
1 stop9h 00m
Southwest
Deal found 4/27![Southwest logo]()
$443
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
MDW
- MBJ
1 stop5h 29m
Delta
Wed 5/131:18 pm
MBJ
- MDW
1 stop7h 51m
Delta
Deal found 4/26![Delta logo]()
$452
This Copa 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 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 4/28![Copa Airlines logo]()
$564
This Air Canada deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:55 am
STL
- MBJ
1 stop26h 25m
Air Canada
Sat 7/2512:30 pm
MBJ
- STL
1 stop25h 32m
Air Canada
Deal found 4/25![Air Canada logo]()
$566
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 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 8/306:25 pm
EVV
- MBJ
2 stops19h 03m
American Airlines
Fri 9/42:20 pm
MBJ
- EVV
1 stop9h 39m
American Airlines
Deal found 4/29![American Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Mon 9/219:35 pm
ORD
- MBJ
1 stop14h 08m
United Airlines
Sat 9/262:40 pm
MBJ
- ORD
1 stop7h 56m
United Airlines
Deal found 4/27![United Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Sun 10/116:06 pm
EVV
- MBJ
1 stop18h 00m
American Airlines
Wed 10/1410:50 am
MBJ
- EVV
2 stops12h 34m
American Airlines
Deal found 4/27![American Airlines logo]()
$363
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 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 United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Tue 7/74:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Deal found 4/26![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 4/27. 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.
Tue 5/129:15 am
STL
- MBJ
1 stop6h 19m
Delta
Tue 5/264:59 pm
MBJ
- STL
1 stop7h 00m
Delta
Deal found 4/27![Delta logo]()
$486
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.
Tue 7/2110:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Mon 7/271:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/29![Southwest logo]()
$471
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Wed 8/52:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 4/27![United Airlines logo]()
$369
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 5/246:48 am
BMI
- MBJ
1 stop9h 29m
American Airlines
Fri 5/292:08 pm
MBJ
- BMI
2 stops9h 51m
American Airlines
Deal found 4/28![American Airlines logo]()
$463
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 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 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.
Sun 8/97:08 am
STL
- MBJ
1 stop5h 58m
Delta
Sat 8/152:29 pm
MBJ
- STL
1 stop6h 21m
Delta
Deal found 4/30![Delta logo]()
$538
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.
Tue 6/26:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sat 6/64:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/30![United Airlines logo]()
$372
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 5/294:34 pm
EVV
- MBJ
2 stops20h 34m
American Airlines
Fri 6/512:48 pm
MBJ
- EVV
1 stop10h 43m
American Airlines
Deal found 4/29![American Airlines logo]()
$477
This Expedia deal was found by Cheapflights users on 4/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:55 am
STL
- KIN
1 stop29h 00m
Air Canada
Tue 9/223:05 pm
KIN
- STL
2 stops27h 36m
Air Canada
Deal found 4/27![Air Canada logo]()
$581
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:10 am
MDW
- MBJ
2 stops9h 45m
Southwest
Sun 7/52:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/26![Southwest logo]()
$490
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:00 am
BMI
- MBJ
1 stop5h 53m
Delta
Sat 5/301:18 pm
MBJ
- BMI
1 stop9h 12m
Delta
Deal found 4/28![Delta logo]()
$564
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Mon 7/136:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sat 7/181:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 4/27![United Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:20 pm
PIA
- MBJ
2 stops20h 48m
American Airlines
Thu 6/182:08 pm
MBJ
- PIA
2 stops19h 15m
American Airlines
Deal found 4/27![American Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 4/27. 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.
Tue 7/1410:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 8/52:10 pm
MBJ
- MDW
1 stop6h 50m
Southwest
Deal found 4/27![Southwest logo]()
$491
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.
Mon 8/318:55 am
STL
- KIN
1 stop29h 00m
Air Canada
Wed 9/23:05 pm
KIN
- STL
1 stop29h 02m
Air Canada
Deal found 4/29![Air Canada logo]()
$609
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:23 am
MDW
- MBJ
1 stop9h 11m
Delta
Tue 6/912:59 pm
MBJ
- MDW
2 stops20h 15m
Delta
Deal found 4/28![Delta logo]()
$567
Last-minute flights from Illinois to JamaicaDiscover last-minute flight deals from Illinois to Jamaica. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Jamaica. Data last updated April 30, 2026 and is based on user searches.
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.
Sun 5/38:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Fri 5/810:17 am
MBJ
- ORD
1 stop13h 37m
American Airlines
Deal found 4/30![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:05 am
ORD
- MBJ
1 stop7h 20m
American Airlines
Wed 5/131:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/26![American Airlines logo]()
$319
This Frontier deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:28 pm
ORD
- MBJ
1 stop19h 43m
Frontier
Wed 5/131:16 pm
MBJ
- ORD
1 stop18h 39m
Frontier
Deal found 4/26![Frontier logo]()
$320
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 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 5/88:46 pm
ORD
- MBJ
1 stop16h 39m
American Airlines
Wed 5/131:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/30![American Airlines logo]()
$342
This Priceline deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:52 pm
ORD
- MBJ
2 stops16h 19m
Frontier
Tue 5/121:16 pm
MBJ
- ORD
1 stop18h 39m
Frontier
Deal found 4/26![Frontier logo]()
$333
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 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Thu 5/212:30 pm
MBJ
- ORD
Nonstop4h 45m
American Airlines
Deal found 4/25![American Airlines logo]()
$318
This Orbitz deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:55 am
ORD
- MBJ
1 stop29h 16m
Multiple Airlines
Thu 5/211:36 pm
MBJ
- ORD
1 stop9h 39m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$330
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 Illinois to JamaicaSearch for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
Search for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Priceline deal was found by Cheapflights users on 4/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/27![Frontier logo]()
$108
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 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 Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com 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 4/26![Spirit Airlines logo]()
$137
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2410:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 4/26![Southwest logo]()
$138
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 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.
Mon 7/610:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 4/30![Southwest logo]()
$148
This Frontier deal was found by Cheapflights users on 4/27. 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 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
Deal found 4/27![Frontier logo]()
$152
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/62:30 pm
ORD
- MBJ
1 stop21h 17m
American Airlines
Deal found 4/26![American Airlines logo]()
$157
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
Find flight deals from Illinois to Jamaica
Keep the following information in mind while searching for Illinois to Jamaica flight deals. Data was last updated April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (American Airlines) |
One-way from | $108 (Priceline) |
Popular in | June |
Cheapest in | January |
Average price | $522 |
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 Illinois 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 April 30, 2026.
Use the filters below to find and compare flights from Illinois 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
Mon 5/18
8:05 am-12:13 pm
Nonstop4h 08m
Montego Bay Sangster Intl
Thu 5/21
2:30 pm-7:15 pm
Nonstop4h 45m
$318
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
$332
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
Mon 9/21
9:35 pm-11:43 am
1 stop14h 08m
Montego Bay Sangster Intl
Sat 9/26
2:40 pm-10:36 pm
1 stop7h 56m
$332
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 7/4
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Tue 7/7
4:12 pm-7:27 am
1 stop15h 15m
$356
EvansvilleMontego Bay
EVV - MBJ
EVVMBJ
Evansville Dress Regional
Sun 8/30
6:25 pm-1:28 pm
2 stops19h 03m
Montego Bay Sangster Intl
Fri 9/4
2:20 pm-11:59 pm
1 stop9h 39m
$357
EvansvilleMontego Bay
EVV - MBJ
EVVMBJ
Evansville Dress Regional
Sun 10/11
6:06 pm-12:06 pm
1 stop18h 00m
Montego Bay Sangster Intl
Wed 10/14
10:50 am-11:24 pm
2 stops12h 34m
$363
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 7/14
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 8/5
2:40 pm-12:45 am
1 stop10h 05m
$369
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
Sat 6/6
4:12 pm-11:26 pm
1 stop7h 14m
$372
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Illinois with our price prediction graph.
ORD-MBJ
MDW-MBJ
STL-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 Illinois to Jamaica
USIL-JM0
ORD-MBJ
MDW-MBJ
STL-MBJ
ORD-KIN
How far ahead should I book a flight from Illinois to Jamaica?
To ensure you get the cheapest price possible for a flight from Illinois to Jamaica, you should look to book at least 87 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Illinois to Jamaica?
Currently, December is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $84). Flying from Illinois 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 IL to JM?
Find hourly flight availability from Illinois 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 April 30, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Jamaica as you normally would.
Weekly flight availability from Illinois to Jamaica
Explore weekly flight availability from Illinois 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 April 30, 2026.
The most flights from USIL to JM0 are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
Related info for your journey
Find useful and relevant information for your journey from Illinois 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.
Alternative routes
Complete your trip
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Top destinations
Alternative routes for Illinois 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 Illinois to Jamaica by cabin class
Find flights from Illinois to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Jamaica flights
Browse other Illinois and Jamaica flight options. Last updated on April 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Jamaica
Find the right flight back to Illinois after your stay in Jamaica
Illinois to Jamaica flights
Consider these flights traveling from Illinois to Jamaica.
Top 6 airlines flying from Illinois to Jamaica
Discover the top 6 airlines that operate flights from Illinois 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 April 30, 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$644 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$468 | Average$653 | FlexibilityNo cancel fee | On-time63% |