$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 23 — May 301
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Jamaica with Cheapflights
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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 23, 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 23, 2026.
This Priceline deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/96:55 am
ORD
- MBJ
1 stop29h 16m
Frontier
Mon 5/111:16 pm
MBJ
- ORD
2 stops33h 57m
Frontier
Deal found 4/18![Frontier logo]()
$303
This FlightHub deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/19![Frontier logo]()
$304
This Justfly.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Mon 5/111:16 pm
MBJ
- MDW
1 stop21h 53m
Frontier
Deal found 4/20![Frontier logo]()
$307
This FlightHub deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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.
Thu 5/71:59 pm
ORD
- MBJ
1 stop22h 12m
Frontier
Mon 5/111:16 pm
MBJ
- ORD
1 stop18h 39m
Frontier
Deal found 4/18![Frontier logo]()
$307
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Fri 5/156:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/191:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/20![Frontier logo]()
$308
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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
Thu 7/301:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/20![Southwest logo]()
$318
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 11/38:05 am
ORD
- MBJ
Nonstop4h 09m
American Airlines
Tue 11/102:19 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 4/21![American Airlines logo]()
$318
This Priceline deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/96:55 am
ORD
- MBJ
1 stop29h 16m
Frontier
Fri 5/151:16 pm
MBJ
- ORD
2 stops29h 28m
Frontier
Deal found 4/21![Frontier logo]()
$320
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/185:35 am
MDW
- MBJ
1 stop6h 00m
Southwest
Sat 5/2311:35 am
MBJ
- MDW
Nonstop4h 10m
Southwest
Deal found 4/22![Southwest logo]()
$322
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 10/258:05 am
ORD
- MBJ
Nonstop4h 01m
American Airlines
Sun 11/12:19 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 4/22![American Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/225:00 am
ORD
- MBJ
1 stop6h 24m
American Airlines
Thu 4/231:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/20![American Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/268:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Wed 4/294:12 pm
MBJ
- ORD
1 stop17h 25m
United Airlines
Deal found 4/20![United Airlines logo]()
$328
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 23, 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 23, 2026.
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/76:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sat 7/114:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Deal found 4/19![United Airlines logo]()
$332
This FlightHub deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Mon 5/111:16 pm
MBJ
- MDW
1 stop21h 53m
Frontier
Deal found 4/18![Frontier logo]()
$352
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/73:45 pm
BMI
- MBJ
2 stops19h 39m
American Airlines
Fri 5/1512:25 pm
MBJ
- BMI
2 stops22h 21m
American Airlines
Deal found 4/19![American Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/206:30 am
MDW
- MBJ
1 stop6h 50m
Southwest
Tue 7/281:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/20![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/76:00 am
BMI
- MBJ
1 stop9h 34m
Delta
Fri 5/152:21 pm
MBJ
- BMI
1 stop8h 09m
Delta
Deal found 4/19![Delta logo]()
$429
This Expedia deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Sun 8/28:55 am
STL
- MBJ
1 stop26h 25m
Air Canada
Thu 8/612:30 pm
MBJ
- STL
1 stop25h 32m
Air Canada
Deal found 4/19![Air Canada logo]()
$478
This Copa Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/221:00 am
ORD
- KIN
1 stop12h 54m
Copa Airlines
Tue 6/302:59 pm
KIN
- ORD
1 stop13h 01m
Copa Airlines
Deal found 4/20![Copa Airlines logo]()
$625
This Orbitz deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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.
Sun 7/198:40 pm
ORD
- KIN
1 stop17h 15m
Multiple Airlines
Fri 7/241:00 pm
KIN
- ORD
1 stop10h 08m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$638
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/25:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Tue 5/52:40 pm
MBJ
- ORD
1 stop17h 13m
United Airlines
Deal found 4/22![United Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 9/71:58 pm
EVV
- MBJ
1 stop21h 39m
American Airlines
Sat 9/123:15 pm
MBJ
- EVV
2 stops20h 51m
American Airlines
Deal found 4/20![American Airlines logo]()
$363
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/55:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Wed 5/134:12 pm
MBJ
- ORD
1 stop7h 32m
United Airlines
Deal found 4/18![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/1310:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Fri 7/1711:45 am
MBJ
- MDW
1 stop9h 35m
Southwest
Deal found 4/19![Southwest logo]()
$443
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 7/46:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Thu 7/91:17 pm
MBJ
- MDW
2 stops19h 51m
Delta
Deal found 4/23![Delta logo]()
$457
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/99:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Tue 5/1212:15 pm
MBJ
- MDW
2 stops19h 20m
Southwest
Deal found 4/19![Southwest logo]()
$447
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/156:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sat 7/181:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 4/20![United Airlines logo]()
$427
This Air Canada deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Thu 6/111:55 pm
ORD
- KIN
2 stops24h 00m
Air Canada
Wed 6/173:05 pm
KIN
- ORD
2 stops16h 40m
Air Canada
Deal found 4/19![Air Canada logo]()
$518
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 9/44:43 pm
PIA
- MBJ
2 stops18h 36m
American Airlines
Mon 9/72:37 pm
MBJ
- PIA
2 stops18h 59m
American Airlines
Deal found 4/19![American Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 7/66:58 pm
MDW
- MBJ
2 stops16h 54m
Delta
Thu 7/91:17 pm
MBJ
- MDW
1 stop8h 58m
Delta
Deal found 4/23![Delta logo]()
$492
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/189:56 pm
ORD
- MBJ
1 stop15h 34m
United Airlines
Sat 5/231:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 4/22![United Airlines logo]()
$440
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 6/17:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Sat 6/62:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/18![Southwest logo]()
$485
This Justfly.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:50 am
ORD
- KIN
1 stop28h 05m
Air Canada
Mon 9/143:05 pm
KIN
- ORD
1 stop17h 55m
Air Canada
Deal found 4/23![Air Canada logo]()
$548
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/69:59 am
STL
- MBJ
1 stop5h 18m
Delta
Fri 5/84:59 pm
MBJ
- STL
1 stop7h 00m
Delta
Deal found 4/21![Delta logo]()
$518
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 10/35:11 pm
STL
- MBJ
2 stops15h 59m
American Airlines
Sat 10/1012:47 pm
MBJ
- STL
1 stop10h 54m
American Airlines
Deal found 4/19![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/278:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Thu 7/92:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 4/20![United Airlines logo]()
$448
This Air Canada deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/111:05 pm
STL
- KIN
2 stops24h 50m
Air Canada
Wed 5/133:05 pm
KIN
- STL
1 stop21h 01m
Air Canada
Deal found 4/19![Air Canada logo]()
$552
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/209:25 am
STL
- MBJ
Nonstop3h 40m
Southwest
Sat 6/272:05 pm
MBJ
- STL
Nonstop3h 45m
Southwest
Deal found 4/20![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/186:00 am
STL
- MBJ
1 stop9h 34m
Delta
Mon 6/14:59 pm
MBJ
- STL
1 stop7h 00m
Delta
Deal found 4/20![Delta logo]()
$544
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/119:56 pm
ORD
- MBJ
1 stop15h 34m
United Airlines
Thu 5/142:40 pm
MBJ
- ORD
1 stop10h 47m
United Airlines
Deal found 4/20![United Airlines logo]()
$452
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/2110:55 am
STL
- MBJ
Nonstop3h 40m
Southwest
Sat 6/272:05 pm
MBJ
- STL
Nonstop3h 45m
Southwest
Deal found 4/19![Southwest logo]()
$504
This Booking.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:05 pm
STL
- KIN
2 stops24h 50m
Air Canada
Wed 5/203:05 pm
KIN
- STL
2 stops29h 20m
Air Canada
Deal found 4/21![Air Canada logo]()
$556
Last-minute flights from Illinois to JamaicaDiscover last-minute flight deals from Illinois to Jamaica. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Jamaica. Data last updated April 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/228:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Thu 4/231:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/20![American Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/268:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Wed 4/294:12 pm
MBJ
- ORD
1 stop17h 25m
United Airlines
Deal found 4/20![United Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/266:00 am
ORD
- MBJ
1 stop9h 10m
United Airlines
Thu 4/304:12 pm
MBJ
- ORD
1 stop7h 32m
United Airlines
Deal found 4/20![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 4/267:35 am
MDW
- MBJ
1 stop6h 05m
Southwest
Thu 4/302:55 pm
MBJ
- MDW
1 stop7h 25m
Southwest
Deal found 4/21![Southwest logo]()
$332
This FlightHub deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/19![Frontier logo]()
$304
This FlightHub deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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.
Thu 5/71:59 pm
ORD
- MBJ
1 stop22h 12m
Frontier
Mon 5/111:16 pm
MBJ
- ORD
1 stop18h 39m
Frontier
Deal found 4/18![Frontier logo]()
$307
This Priceline deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/96:55 am
ORD
- MBJ
1 stop29h 16m
Frontier
Mon 5/111:16 pm
MBJ
- ORD
2 stops33h 57m
Frontier
Deal found 4/18![Frontier logo]()
$303
This Justfly.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Mon 5/111:16 pm
MBJ
- MDW
1 stop21h 53m
Frontier
Deal found 4/20![Frontier logo]()
$307
This Priceline deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/96:55 am
ORD
- MBJ
1 stop29h 16m
Frontier
Fri 5/151:16 pm
MBJ
- ORD
2 stops29h 28m
Frontier
Deal found 4/21![Frontier logo]()
$320
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Fri 5/156:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/191:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/20![Frontier logo]()
$308
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/20![American Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/185:35 am
MDW
- MBJ
1 stop6h 00m
Southwest
Sat 5/2311:35 am
MBJ
- MDW
Nonstop4h 10m
Southwest
Deal found 4/22![Southwest logo]()
$322
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 23, 2026.
Search for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Frontier deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/196:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/19![Frontier logo]()
$108
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/48:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 4/20![American Airlines logo]()
$138
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 6/2010:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 4/21![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/185:35 am
MDW
- MBJ
1 stop6h 00m
Southwest
Deal found 4/19![Southwest logo]()
$142
This FlightHub deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Sun 5/176:50 am
ORD
- MBJ
1 stop29h 21m
Frontier
Deal found 4/19![Frontier logo]()
$145
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:00 pm
ORD
- MBJ
1 stop19h 08m
American Airlines
Deal found 4/21![American Airlines logo]()
$148
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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
Deal found 4/20![Frontier logo]()
$152
This FlightHub deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:15 pm
MDW
- MBJ
1 stop21h 56m
Frontier
Deal found 4/19![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Mon 5/184:05 pm
ORD
- MBJ
2 stops20h 06m
Frontier
Deal found 4/19![Frontier logo]()
$156
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/186:00 pm
ORD
- MBJ
1 stop19h 09m
American Airlines
Deal found 4/20![American Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Sun 5/175:05 am
ORD
- MBJ
1 stop7h 26m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 7/146:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Deal found 4/18![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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (FlightHub) |
One-way from | $108 (Frontier) |
Popular in | June |
Cheapest in | January |
Average price | $522 |
Good round-trip deal | $417 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 23, 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
Tue 7/7
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sat 7/11
4:33 pm-12:45 am
1 stop8h 12m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/2
5:30 am-1:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Tue 5/5
2:40 pm-7:53 am
1 stop17h 13m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 5/5
5:30 am-1:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Wed 5/13
4:12 pm-11:44 pm
1 stop7h 32m
$332
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 5/9
11:59 am-12:11 pm
1 stop24h 12m
Montego Bay Sangster Intl
Mon 5/11
1:16 pm-11:09 am
1 stop21h 53m
$352
BloomingtonMontego Bay
BMI - MBJ
BMIMBJ
Bloomington-Normal
Thu 5/7
3:45 pm-11:24 am
2 stops19h 39m
Montego Bay Sangster Intl
Fri 5/15
12:25 pm-10:46 am
2 stops22h 21m
$359
EvansvilleMontego Bay
EVV - MBJ
EVVMBJ
Evansville Dress Regional
Mon 9/7
1:58 pm-11:37 am
1 stop21h 39m
Montego Bay Sangster Intl
Sat 9/12
3:15 pm-12:06 pm
2 stops20h 51m
$363
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 7/20
6:30 am-1:20 pm
1 stop6h 50m
Montego Bay Sangster Intl
Tue 7/28
1:50 pm-5:50 pm
Nonstop4h 00m
$417
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 7/15
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sat 7/18
1:52 pm-6:15 pm
Nonstop4h 23m
$427
BloomingtonMontego Bay
BMI - MBJ
BMIMBJ
Bloomington-Normal
Thu 5/7
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Fri 5/15
2:21 pm-10:30 pm
1 stop8h 09m
$429
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Mon 5/18
9:56 pm-1:30 pm
1 stop15h 34m
Montego Bay Sangster Intl
Sat 5/23
1:52 pm-6:15 pm
Nonstop4h 23m
$440
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.
MDW-MBJ
ORD-MBJ
ORD-KIN
MDW-KIN
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
MDW-MBJ
ORD-MBJ
ORD-KIN
MDW-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 23, 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 23, 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.
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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 23, 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$456 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$144 | Average$675 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$546 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$302 | Average$528 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$328 | Average$644 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$468 | Average$653 | FlexibilityNo cancel fee | On-time63% |