$189+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Aug 30 — Sep 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 July 31, 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 July 31, 2026.
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:00 am
MLI
- MBJ
1 stop5h 48m
Delta
Tue 10/61:16 pm
MBJ
- MLI
1 stop9h 14m
Delta
Deal found 7/28![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:38 pm
PIA
- MBJ
2 stops17h 22m
American Airlines
Mon 12/74:23 pm
MBJ
- PIA
2 stops19h 33m
American Airlines
Deal found 7/27![American Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:08 am
BMI
- MBJ
1 stop5h 40m
Delta
Tue 10/61:16 pm
MBJ
- BMI
1 stop9h 20m
Delta
Deal found 7/28![Delta logo]()
$402
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:43 pm
PIA
- MBJ
2 stops20h 10m
American Airlines
Tue 10/65:13 pm
MBJ
- PIA
2 stops22h 59m
American Airlines
Deal found 7/28![American Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:30 pm
BMI
- MBJ
2 stops21h 42m
American Airlines
Mon 12/74:23 pm
MBJ
- BMI
2 stops22h 34m
American Airlines
Deal found 7/27![American Airlines logo]()
$413
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:55 pm
ORD
- MBJ
1 stop22h 30m
Air Canada
Sun 11/152:20 pm
MBJ
- ORD
2 stops20h 03m
Air Canada
Deal found 7/31![Air Canada logo]()
$420
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:50 pm
ORD
- MBJ
1 stop15h 00m
Air Canada
Sat 11/146:20 pm
MBJ
- ORD
1 stop16h 03m
Air Canada
Deal found 7/31![Air Canada logo]()
$422
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:58 pm
ORD
- MBJ
2 stops19h 27m
Air Canada
Sat 11/76:20 pm
MBJ
- ORD
2 stops17h 47m
Air Canada
Deal found 7/31![Air Canada logo]()
$424
This FlightHub deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:21 pm
ORD
- MBJ
2 stops40h 59m
Air Canada
Sun 10/251:20 pm
MBJ
- ORD
1 stop21h 47m
Air Canada
Deal found 7/31![Air Canada logo]()
$425
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:40 am
ORD
- MBJ
Nonstop4h 08m
United Airlines
Sat 11/72:54 pm
MBJ
- ORD
Nonstop4h 26m
United Airlines
Deal found 7/31![United Airlines logo]()
$428
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:58 pm
ORD
- MBJ
2 stops22h 22m
Air Canada
Tue 12/11:50 pm
MBJ
- ORD
2 stops22h 17m
Air Canada
Deal found 7/31![Air Canada logo]()
$430
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:49 pm
ORD
- MBJ
1 stop17h 34m
American Airlines
Thu 8/272:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Deal found 7/30![American Airlines logo]()
$432
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 July 31, 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 July 31, 2026.
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/123:30 pm
EVV
- MBJ
2 stops20h 28m
American Airlines
Tue 2/94:27 pm
MBJ
- EVV
2 stops20h 05m
American Airlines
Deal found 7/31![American Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:08 am
BMI
- MBJ
1 stop5h 40m
Delta
Tue 10/61:16 pm
MBJ
- BMI
1 stop9h 20m
Delta
Deal found 7/28![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:45 am
MLI
- MBJ
1 stop6h 01m
United Airlines
Fri 1/153:55 pm
MBJ
- MLI
2 stops19h 19m
United Airlines
Deal found 7/28![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Tue 9/2912:55 pm
MBJ
- MDW
1 stop8h 30m
Southwest
Deal found 7/31![Southwest logo]()
$442
This Copa Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:20 pm
ORD
- MBJ
1 stop19h 57m
Copa Airlines
Sun 9/2012:22 pm
MBJ
- ORD
1 stop12h 40m
Copa Airlines
Deal found 7/31![Copa Airlines logo]()
$489
This JetBlue deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:30 am
ORD
- KIN
1 stop9h 34m
JetBlue
Thu 11/122:55 pm
KIN
- ORD
1 stop9h 49m
JetBlue
Deal found 7/29![JetBlue logo]()
$533
This Air Canada deal was found by Cheapflights users on 7/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:10 pm
STL
- KIN
2 stops22h 15m
Air Canada
Wed 9/163:05 pm
KIN
- STL
1 stop22h 55m
Air Canada
Deal found 7/26![Air Canada logo]()
$585
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:38 pm
PIA
- MBJ
2 stops17h 22m
American Airlines
Mon 12/74:23 pm
MBJ
- PIA
2 stops19h 33m
American Airlines
Deal found 7/27![American Airlines logo]()
$397
This Mytrip deal was found by Cheapflights users on 7/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:10 pm
STL
- KIN
2 stops22h 15m
Multiple Airlines
Wed 9/169:12 am
KIN
- STL
3 stops28h 48m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$814
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:27 am
ORD
- MBJ
1 stop7h 33m
Delta
Wed 10/2812:59 pm
MBJ
- ORD
1 stop8h 44m
Delta
Deal found 7/28![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Sat 9/1911:40 am
MBJ
- MDW
1 stop8h 55m
Southwest
Deal found 7/28![Southwest logo]()
$442
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/234:03 pm
BMI
- MBJ
2 stops19h 55m
American Airlines
Sat 1/302:44 pm
MBJ
- BMI
2 stops24h 13m
American Airlines
Deal found 7/27![American Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:50 pm
STL
- MBJ
2 stops18h 24m
United Airlines
Mon 11/91:25 pm
MBJ
- STL
1 stop9h 27m
United Airlines
Deal found 7/30![United Airlines logo]()
$481
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:10 am
ORD
- MBJ
2 stops8h 25m
Delta
Thu 10/294:44 pm
MBJ
- ORD
2 stops14h 57m
Delta
Deal found 7/28![Delta logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:01 am
ORD
- MBJ
1 stop27h 16m
Copa Airlines
Tue 9/1512:22 pm
MBJ
- ORD
1 stop12h 40m
Copa Airlines
Deal found 7/27![Copa Airlines logo]()
$510
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:30 pm
BMI
- MBJ
2 stops21h 42m
American Airlines
Mon 12/74:23 pm
MBJ
- BMI
2 stops23h 30m
American Airlines
Deal found 7/29![American Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Fri 10/3012:50 pm
MBJ
- MDW
1 stop9h 10m
Southwest
Deal found 7/31![Southwest logo]()
$480
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:40 am
ORD
- MBJ
1 stop8h 54m
Delta
Thu 8/274:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Deal found 7/30![Delta logo]()
$447
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:45 pm
ORD
- MBJ
1 stop15h 58m
United Airlines
Tue 9/2212:52 pm
MBJ
- ORD
1 stop9h 23m
United Airlines
Deal found 7/27![United Airlines logo]()
$498
This Copa Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:13 pm
ORD
- KIN
1 stop22h 39m
Copa Airlines
Wed 11/252:58 pm
KIN
- ORD
1 stop22h 48m
Copa Airlines
Deal found 7/31![Copa Airlines logo]()
$516
This JetBlue deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am
ORD
- KIN
1 stop6h 45m
JetBlue
Mon 9/213:05 pm
KIN
- ORD
1 stop8h 03m
JetBlue
Deal found 7/30![JetBlue logo]()
$573
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:30 am
STL
- MBJ
2 stops8h 15m
Southwest
Tue 11/171:50 pm
MBJ
- STL
2 stops9h 05m
Southwest
Deal found 7/29![Southwest logo]()
$481
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/163:58 pm
MLI
- MBJ
2 stops18h 45m
American Airlines
Sun 1/242:44 pm
MBJ
- MLI
2 stops20h 46m
American Airlines
Deal found 7/27![American Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:01 am
BMI
- MBJ
1 stop9h 34m
Delta
Mon 12/72:20 pm
MBJ
- BMI
1 stop9h 00m
Delta
Deal found 7/29![Delta logo]()
$461
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:05 pm
PIA
- MBJ
2 stops21h 34m
United Airlines
Wed 10/282:01 pm
MBJ
- PIA
1 stop8h 57m
United Airlines
Deal found 7/28![United Airlines logo]()
$517
This Air Canada deal was found by Cheapflights users on 7/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:10 pm
STL
- KIN
2 stops25h 45m
Air Canada
Wed 9/233:05 pm
KIN
- STL
1 stop22h 55m
Air Canada
Deal found 7/26![Air Canada logo]()
$639
This Copa Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/143:20 pm
ORD
- KIN
1 stop22h 34m
Copa Airlines
Mon 9/212:57 pm
KIN
- ORD
1 stop10h 05m
Copa Airlines
Deal found 7/31![Copa Airlines logo]()
$546
This Southwest deal was found by Cheapflights users on 7/27. 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 9/86:15 am
MDW
- MBJ
1 stop5h 40m
Southwest
Sat 9/121:25 pm
MBJ
- MDW
1 stop7h 10m
Southwest
Deal found 7/27![Southwest logo]()
$512
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:05 pm
MLI
- MBJ
2 stops21h 38m
United Airlines
Sat 9/192:40 pm
MBJ
- MLI
2 stops21h 51m
United Airlines
Deal found 7/29![United Airlines logo]()
$517
This JetBlue deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/62:45 pm
ORD
- KIN
1 stop6h 37m
JetBlue
Wed 9/93:05 pm
KIN
- ORD
1 stop8h 03m
JetBlue
Deal found 7/27![JetBlue logo]()
$631
Last-minute flights from Illinois to JamaicaDiscover last-minute flight deals from Illinois to Jamaica. Data last updated July 31, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Jamaica. Data last updated July 31, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:00 am
ORD
- MBJ
1 stop9h 23m
American Airlines
Thu 8/2012:47 pm
MBJ
- ORD
1 stop19h 58m
American Airlines
Deal found 7/30![American Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:00 am
ORD
- KIN
1 stop14h 42m
American Airlines
Sat 8/222:00 pm
KIN
- ORD
1 stop17h 34m
American Airlines
Deal found 7/29![American Airlines logo]()
$468
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 8/218:37 am
ORD
- KIN
1 stop8h 05m
American Airlines
Sun 8/232:00 pm
KIN
- ORD
1 stop9h 30m
American Airlines
Deal found 7/27![American Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:42 pm
MDW
- MBJ
2 stops20h 52m
Delta
Thu 8/274:59 pm
MBJ
- MDW
2 stops19h 40m
Delta
Deal found 7/30![Delta logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/223:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Fri 8/2811:23 am
MBJ
- ORD
1 stop13h 39m
Copa Airlines
Deal found 7/29![Copa Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:49 pm
ORD
- MBJ
1 stop17h 34m
American Airlines
Fri 8/282:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Deal found 7/27![American Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:18 pm
ORD
- MBJ
2 stops22h 16m
Delta
Sat 8/294:59 pm
MBJ
- ORD
1 stop6h 58m
Delta
Deal found 7/30![Delta logo]()
$485
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:49 pm
ORD
- MBJ
1 stop17h 34m
American Airlines
Thu 8/272:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Deal found 7/30![American Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:40 am
ORD
- MBJ
1 stop8h 54m
Delta
Thu 8/274:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Deal found 7/29![Delta logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:17 pm
STL
- MBJ
1 stop18h 00m
Frontier
Sat 9/51:32 pm
MBJ
- STL
1 stop27h 50m
Frontier
Deal found 7/30![Frontier logo]()
$477
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Wed 9/21:55 pm
MBJ
- MDW
1 stop6h 50m
Southwest
Deal found 7/30![Southwest logo]()
$442
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:11 am
MDW
- MBJ
1 stop9h 23m
Delta
Wed 9/21:09 pm
MBJ
- MDW
1 stop9h 27m
Delta
Deal found 7/30![Delta logo]()
$480
One-way flights from Illinois to JamaicaSearch for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
Search for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:05 am
ORD
- KIN
2 stops7h 54m
American Airlines
Deal found 7/28![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:00 am
ORD
- MBJ
Nonstop4h 12m
American Airlines
Deal found 7/30![American Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
ORD
- MBJ
1 stop10h 16m
American Airlines
Deal found 7/29![American Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:35 pm
ORD
- KIN
1 stop19h 29m
American Airlines
Deal found 7/28![American Airlines logo]()
$195
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Mon 10/268:40 am
ORD
- MBJ
Nonstop4h 08m
United Airlines
Deal found 7/26![United Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:30 am
ORD
- MBJ
1 stop6h 30m
Delta
Deal found 7/29![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:11 pm
MDW
- MBJ
2 stops18h 22m
Delta
Deal found 7/29![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:25 am
MDW
- MBJ
1 stop6h 20m
Southwest
Deal found 7/30![Southwest logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:35 am
STL
- MBJ
1 stop26h 49m
Frontier
Deal found 7/30![Frontier logo]()
$200
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:00 am
MDW
- MBJ
1 stop9h 25m
Southwest
Deal found 7/28![Southwest logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:17 pm
STL
- MBJ
1 stop18h 00m
Frontier
Deal found 7/29![Frontier logo]()
$201
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:29 pm
ORD
- MBJ
2 stops22h 00m
Delta
Deal found 7/29![Delta logo]()
$203
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 July 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $392 (Delta) |
One-way from | $189 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $553 |
Good round-trip deal | $547 or less |
Good one-way deal | $196 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from 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 July 31, 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
EvansvilleMontego Bay
EVV - MBJ
EVVMBJ
Evansville Dress Regional
Tue 1/12
3:30 pm-12:58 pm
2 stops20h 28m
Montego Bay Sangster Intl
Tue 2/9
4:27 pm-11:32 am
2 stops20h 05m
$397
PeoriaMontego Bay
PIA - MBJ
PIAMBJ
Greater Peoria
Thu 12/3
6:38 pm-1:00 pm
2 stops17h 22m
Montego Bay Sangster Intl
Mon 12/7
4:23 pm-10:56 am
2 stops19h 33m
$397
BloomingtonMontego Bay
BMI - MBJ
BMIMBJ
Bloomington-Normal
Fri 10/2
6:08 am-11:48 am
1 stop5h 40m
Montego Bay Sangster Intl
Tue 10/6
1:16 pm-10:36 pm
1 stop9h 20m
$402
BloomingtonMontego Bay
BMI - MBJ
BMIMBJ
Bloomington-Normal
Sat 1/23
4:03 pm-12:58 pm
2 stops19h 55m
Montego Bay Sangster Intl
Sat 1/30
2:44 pm-1:57 pm
2 stops24h 13m
$410
MolineMontego Bay
MLI - MBJ
MLIMBJ
Moline Quad-City
Fri 1/8
6:45 am-1:46 pm
1 stop6h 01m
Montego Bay Sangster Intl
Fri 1/15
3:55 pm-10:14 am
2 stops19h 19m
$415
BloomingtonMontego Bay
BMI - MBJ
BMIMBJ
Bloomington-Normal
Thu 12/3
3:30 pm-2:12 pm
2 stops21h 42m
Montego Bay Sangster Intl
Mon 12/7
4:23 pm-2:53 pm
2 stops23h 30m
$428
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 9/22
6:30 am-12:55 pm
1 stop6h 25m
Montego Bay Sangster Intl
Tue 9/29
12:55 pm-9:25 pm
1 stop8h 30m
$442
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 10/24
5:27 am-1:00 pm
1 stop7h 33m
Montego Bay Sangster Intl
Wed 10/28
12:59 pm-9:43 pm
1 stop8h 44m
$442
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 9/12
5:55 am-12:25 pm
1 stop6h 30m
Montego Bay Sangster Intl
Sat 9/19
11:40 am-8:35 pm
1 stop8h 55m
$442
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 10/24
7:10 am-3:35 pm
2 stops8h 25m
Montego Bay Sangster Intl
Thu 10/29
4:44 pm-7:41 am
2 stops14h 57m
$447
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-KIN
ORD-MBJ
MDW-MBJ
STL-MBJ
STL-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-KIN
ORD-MBJ
MDW-MBJ
STL-MBJ
What is the cheapest month to book a flight from Illinois to Jamaica?
Currently, April is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $482). Flying from Illinois to Jamaica in December is currently the most expensive (average of $673). 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 July 31, 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 July 31, 2026.
The most flights from USIL to JM0 are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from 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.
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 July 31, 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 July 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$686 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$610 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$297 | Average$510 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$302 | Average$529 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$317 | Average$648 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |