$119+ 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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Apr 9 — Apr 161
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 March 10, 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 March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/78:45 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Sat 3/142:20 pm
MBJ
- MDW
Nonstop4h 15m
Southwest
Deal found 3/5![Southwest logo]()
$298
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 11/299:45 am
ORD
- MBJ
Nonstop4h 16m
American Airlines
Mon 12/143:12 pm
MBJ
- ORD
Nonstop4h 47m
American Airlines
Deal found 3/8![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 11/103:14 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 3/6![American Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/279:20 am
ORD
- MBJ
Nonstop4h 10m
American Airlines
Mon 6/12:30 pm
MBJ
- ORD
Nonstop4h 46m
American Airlines
Deal found 3/7![American Airlines logo]()
$303
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/198:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Thu 4/234:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/8![United Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/96:35 am
MDW
- MBJ
1 stop7h 55m
Southwest
Wed 3/1112:55 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 3/5![Southwest logo]()
$312
This American Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:45 pm
ORD
- MBJ
1 stop16h 28m
American Airlines
Sat 12/124:23 pm
MBJ
- ORD
1 stop7h 34m
American Airlines
Deal found 3/5![American Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/128:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Sun 5/173:20 pm
MBJ
- ORD
1 stop8h 14m
American Airlines
Deal found 3/6![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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
Mon 5/1110:17 am
MBJ
- ORD
1 stop22h 13m
American Airlines
Deal found 3/9![American Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/297:15 am
ORD
- MBJ
1 stop6h 10m
American Airlines
Sat 5/210:13 am
MBJ
- ORD
1 stop9h 09m
American Airlines
Deal found 3/6![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/138:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Sun 5/173:20 pm
MBJ
- ORD
1 stop8h 14m
American Airlines
Deal found 3/5![American Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/265:15 am
MDW
- MBJ
1 stop9h 05m
Southwest
Thu 4/3012:35 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 3/5![Southwest logo]()
$333
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 March 10, 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 March 10, 2026.
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/138:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 4/182:40 pm
MBJ
- ORD
1 stop8h 35m
United Airlines
Deal found 3/9![United Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/236:23 pm
EVV
- MBJ
2 stops17h 01m
American Airlines
Wed 4/2910:17 am
MBJ
- EVV
2 stops13h 37m
American Airlines
Deal found 3/9![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/139:59 am
STL
- MBJ
1 stop5h 18m
Delta
Fri 4/1712:44 pm
MBJ
- STL
1 stop10h 52m
Delta
Deal found 3/5![Delta logo]()
$414
This Air Canada deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 6/67:05 am
STL
- MBJ
1 stop28h 15m
Air Canada
Sun 6/1412:30 pm
MBJ
- STL
1 stop23h 36m
Air Canada
Deal found 3/7![Air Canada logo]()
$416
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/77:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Sun 6/141:35 pm
MBJ
- MDW
2 stops10h 05m
Southwest
Deal found 3/6![Southwest logo]()
$515
This Mytrip deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/412:45 pm
ORD
- KIN
3 stops22h 50m
Spirit Airlines
Wed 4/812:32 pm
KIN
- ORD
2 stops23h 18m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$566
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 7/286:00 am
ORD
- MBJ
1 stop9h 10m
United Airlines
Sat 8/14:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Deal found 3/9![United Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 7/56:23 pm
EVV
- MBJ
1 stop18h 50m
American Airlines
Fri 7/105:17 pm
MBJ
- EVV
2 stops19h 00m
American Airlines
Deal found 3/5![American Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/258:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Tue 4/284:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/8![United Airlines logo]()
$312
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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.
Thu 4/237:43 pm
PIA
- MBJ
1 stop17h 07m
United Airlines
Thu 4/304:12 pm
MBJ
- PIA
2 stops20h 45m
United Airlines
Deal found 3/8![United Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/216:30 am
MLI
- MBJ
2 stops8h 40m
United Airlines
Tue 4/284:12 pm
MBJ
- MLI
2 stops20h 15m
United Airlines
Deal found 3/7![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/29:31 am
STL
- MBJ
1 stop5h 46m
Delta
Sat 5/92:21 pm
MBJ
- STL
1 stop9h 38m
Delta
Deal found 3/8![Delta logo]()
$464
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 8/245:26 pm
MLI
- MBJ
2 stops18h 37m
American Airlines
Fri 8/2810:25 am
MBJ
- MLI
1 stop11h 46m
American Airlines
Deal found 3/8![American Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/96:23 am
MDW
- MBJ
1 stop6h 33m
Delta
Fri 5/151:18 pm
MBJ
- MDW
1 stop7h 51m
Delta
Deal found 3/5![Delta logo]()
$472
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/138:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Fri 4/171:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/8![United Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/16:00 am
ORD
- MBJ
1 stop5h 35m
Southwest
Mon 5/412:35 pm
MBJ
- ORD
2 stops21h 10m
Southwest
Deal found 3/9![Southwest logo]()
$536
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/176:55 pm
STL
- MBJ
1 stop14h 18m
American Airlines
Tue 4/2112:56 pm
MBJ
- STL
1 stop9h 28m
American Airlines
Deal found 3/7![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 8/227:10 am
ORD
- MBJ
2 stops8h 24m
Delta
Tue 8/254:59 pm
MBJ
- ORD
2 stops14h 27m
Delta
Deal found 3/5![Delta logo]()
$477
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:10 am
MDW
- MBJ
1 stop7h 40m
Southwest
Sat 8/11:40 pm
MBJ
- MDW
1 stop8h 45m
Southwest
Deal found 3/9![Southwest logo]()
$545
This American Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/186:53 pm
STL
- MBJ
1 stop14h 20m
American Airlines
Mon 4/204:37 pm
MBJ
- STL
2 stops17h 07m
American Airlines
Deal found 3/5![American Airlines logo]()
$452
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/56:00 am
STL
- MBJ
1 stop7h 30m
United Airlines
Tue 5/122:40 pm
MBJ
- STL
1 stop7h 50m
United Airlines
Deal found 3/8![United Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/216:00 am
BMI
- MBJ
1 stop6h 54m
Delta
Tue 4/2812:44 pm
MBJ
- BMI
1 stop9h 37m
Delta
Deal found 3/7![Delta logo]()
$501
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/265:05 am
MDW
- MBJ
1 stop8h 35m
Southwest
Tue 4/2812:15 pm
MBJ
- MDW
1 stop9h 10m
Southwest
Deal found 3/8![Southwest logo]()
$575
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/216:00 am
PIA
- MBJ
1 stop6h 13m
American Airlines
Tue 4/2812:56 pm
MBJ
- PIA
2 stops22h 46m
American Airlines
Deal found 3/7![American Airlines logo]()
$487
This Air Canada deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/181:00 pm
STL
- KIN
2 stops24h 55m
Air Canada
Thu 5/283:05 pm
KIN
- STL
1 stop21h 01m
Air Canada
Deal found 3/6![Air Canada logo]()
$723
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/186:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Tue 4/212:10 pm
MBJ
- MDW
1 stop8h 18m
Delta
Deal found 3/7![Delta logo]()
$507
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/198:15 pm
STL
- MBJ
1 stop16h 35m
United Airlines
Fri 4/244:12 pm
MBJ
- STL
2 stops18h 33m
United Airlines
Deal found 3/6![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 7/155:10 am
MDW
- MBJ
2 stops9h 45m
Southwest
Sun 7/192:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 3/6![Southwest logo]()
$583
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/215:15 am
MLI
- MBJ
1 stop6h 58m
American Airlines
Tue 4/2812:56 pm
MBJ
- MLI
2 stops22h 38m
American Airlines
Deal found 3/7![American Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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
- MBJ
1 stop9h 11m
Delta
Wed 6/101:10 pm
MBJ
- MDW
1 stop8h 35m
Delta
Deal found 3/8![Delta logo]()
$507
Last-minute flights from Illinois to JamaicaDiscover last-minute flight deals from Illinois to Jamaica. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Jamaica. Data last updated March 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/96:35 am
MDW
- MBJ
1 stop7h 55m
Southwest
Wed 3/1112:55 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 3/5![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/108:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Tue 3/171:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Deal found 3/9![United Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/118:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Wed 4/154:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/10![United Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/138:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Thu 4/161:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/7![United Airlines logo]()
$302
This Priceline deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
Mon 4/135:05 am
ORD
- MBJ
1 stop6h 00m
Spirit Airlines
Thu 4/161:21 pm
MBJ
- ORD
1 stop11h 03m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/198:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Thu 4/231:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/6![United Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/236:23 pm
EVV
- MBJ
2 stops17h 01m
American Airlines
Wed 4/2910:17 am
MBJ
- EVV
2 stops13h 37m
American Airlines
Deal found 3/9![American Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/258:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Wed 4/294:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/6![United Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/255:00 am
ORD
- MBJ
1 stop9h 15m
American Airlines
Tue 4/2812:56 pm
MBJ
- ORD
1 stop25h 40m
American Airlines
Deal found 3/6![American Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/265:15 am
MDW
- MBJ
1 stop9h 05m
Southwest
Thu 4/3012:35 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 3/5![Southwest logo]()
$333
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/297:15 am
ORD
- MBJ
1 stop6h 10m
American Airlines
Sat 5/210:13 am
MBJ
- ORD
1 stop9h 09m
American Airlines
Deal found 3/6![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/295:00 am
ORD
- MBJ
1 stop8h 25m
American Airlines
Mon 5/412:25 pm
MBJ
- ORD
1 stop21h 46m
American Airlines
Deal found 3/8![American Airlines logo]()
$324
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 March 10, 2026.
Search for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- MBJ
1 stop6h 00m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:05 am
ORD
- MBJ
1 stop7h 11m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$120
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/198:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Deal found 3/9![United Airlines logo]()
$128
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/119:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 3/9![Southwest logo]()
$128
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/118:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 3/9![United Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/195:15 am
MDW
- MBJ
1 stop9h 05m
Southwest
Deal found 3/9![Southwest logo]()
$132
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/138:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 3/6![American Airlines logo]()
$133
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/35:00 am
ORD
- MBJ
1 stop8h 55m
American Airlines
Deal found 3/6![American Airlines logo]()
$137
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/128:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Deal found 3/9![United Airlines logo]()
$138
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/88:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 3/9![United Airlines logo]()
$142
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/79:35 pm
ORD
- MBJ
1 stop17h 35m
United Airlines
Deal found 3/6![United Airlines logo]()
$144
This Super.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:05 am
ORD
- KIN
1 stop6h 30m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$145
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 March 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $298 (United Airlines) |
One-way from | $119 (Cheapflightsfares) |
Popular in | June |
Cheapest in | January |
Average price | $590 |
Good round-trip deal | $336 or less |
Good one-way deal | $218 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 March 10, 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 4/13
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Sat 4/18
2:40 pm-11:15 pm
1 stop8h 35m
$308
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 7/28
6:00 am-3:10 pm
1 stop9h 10m
Montego Bay Sangster Intl
Sat 8/1
4:33 pm-12:45 am
1 stop8h 12m
$312
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 4/25
8:45 am-3:10 pm
1 stop6h 25m
Montego Bay Sangster Intl
Tue 4/28
4:12 pm-11:43 pm
1 stop7h 31m
$312
EvansvilleMontego Bay
EVV - MBJ
EVVMBJ
Evansville Dress Regional
Thu 4/23
6:23 pm-11:24 am
2 stops17h 01m
Montego Bay Sangster Intl
Wed 4/29
10:17 am-11:54 pm
2 stops13h 37m
$337
PeoriaMontego Bay
PIA - MBJ
PIAMBJ
Greater Peoria
Thu 4/23
7:43 pm-12:50 pm
1 stop17h 07m
Montego Bay Sangster Intl
Thu 4/30
4:12 pm-12:57 pm
2 stops20h 45m
$337
MolineMontego Bay
MLI - MBJ
MLIMBJ
Moline Quad-City
Tue 4/21
6:30 am-3:10 pm
2 stops8h 40m
Montego Bay Sangster Intl
Tue 4/28
4:12 pm-12:27 pm
2 stops20h 15m
$337
EvansvilleMontego Bay
EVV - MBJ
EVVMBJ
Evansville Dress Regional
Sun 7/5
6:23 pm-1:13 pm
1 stop18h 50m
Montego Bay Sangster Intl
Fri 7/10
5:17 pm-12:17 pm
2 stops19h 00m
$343
Quickest round-trip
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Mon 4/13
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Fri 4/17
1:52 pm-6:15 pm
Nonstop4h 23m
$366
St. LouisMontego Bay
STL - MBJ
STLMBJ
Lambert-St Louis
Mon 4/13
9:59 am-3:17 pm
1 stop5h 18m
Montego Bay Sangster Intl
Fri 4/17
12:44 pm-11:36 pm
1 stop10h 52m
$414
St. LouisMontego Bay
STL - MBJ
STLMBJ
Lambert-St Louis
Tue 5/5
6:00 am-1:30 pm
1 stop7h 30m
Montego Bay Sangster Intl
Tue 5/12
2:40 pm-10:30 pm
1 stop7h 50m
$414
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
ORD-KIN
EVV-MBJ
STL-MBJ
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
ORD-KIN
EVV-MBJ
What is the cheapest month to book a flight from Illinois to Jamaica?
Currently, January is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $95). Flying from Illinois to Jamaica in August is currently the most expensive (average of $384). 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 March 10, 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 March 10, 2026.
The most flights from USIL to JM0 are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 March 10, 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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$455 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$144 | Average$672 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$597 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$356 | Average$557 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$379 | Average$659 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$518 | Average$683 | FlexibilityNo cancel fee | On-time63% |