$209+ Cheap flights from Jamaica to Illinois
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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — ORD
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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Cheapest flights from Jamaica to IllinoisExplore the most affordable flight options available from Jamaica to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
Explore the most affordable flight options available from Jamaica to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
This FlightHub deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:20 pm
MBJ
- ORD
1 stop21h 47m
Air Canada
Sat 10/315:54 pm
ORD
- MBJ
1 stop19h 31m
Air Canada
Deal found 8/2![Air Canada logo]()
$382
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.
Mon 11/236:20 pm
MBJ
- ORD
1 stop16h 03m
Air Canada
Sun 11/294:30 pm
ORD
- MBJ
1 stop23h 50m
Air Canada
Deal found 7/31![Air Canada logo]()
$385
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Tue 9/89:00 am
ORD
- MBJ
Nonstop4h 12m
American Airlines
Deal found 8/2![American Airlines logo]()
$391
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.
Sat 9/122:40 pm
MBJ
- ORD
1 stop29h 25m
United Airlines
Sat 9/195:45 pm
ORD
- MBJ
1 stop17h 58m
United Airlines
Deal found 7/30![United Airlines logo]()
$402
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.
Sat 9/54:59 pm
MBJ
- ORD
2 stops17h 43m
Delta
Sat 9/195:30 pm
ORD
- MBJ
1 stop18h 03m
Delta
Deal found 7/29![Delta logo]()
$403
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 9/71:09 pm
MBJ
- MDW
1 stop9h 27m
Delta
Fri 9/187:01 pm
MDW
- MBJ
2 stops16h 32m
Delta
Deal found 7/29![Delta logo]()
$403
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 8/225:08 pm
MBJ
- ORD
1 stop14h 26m
American Airlines
Mon 8/244:00 pm
ORD
- MBJ
1 stop22h 23m
American Airlines
Deal found 7/29![American Airlines logo]()
$406
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.
Sat 9/121:50 pm
MBJ
- MDW
1 stop7h 10m
Southwest
Sat 9/195:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Deal found 7/31![Southwest logo]()
$406
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.
Fri 9/255:16 pm
MBJ
- ORD
2 stops14h 42m
American Airlines
Mon 9/285:20 am
ORD
- MBJ
2 stops7h 33m
American Airlines
Deal found 7/31![American Airlines logo]()
$411
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 8/296:05 am
KIN
- ORD
1 stop17h 25m
American Airlines
Sat 9/196:00 am
ORD
- KIN
1 stop10h 02m
American Airlines
Deal found 7/29![American Airlines logo]()
$432
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 9/132:00 pm
MBJ
- MDW
1 stop8h 30m
Southwest
Sun 9/205:00 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 7/30![Southwest logo]()
$446
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:55 pm
KIN
- ORD
1 stop9h 49m
JetBlue
Mon 9/77:00 am
ORD
- KIN
1 stop10h 18m
JetBlue
Deal found 7/31![JetBlue logo]()
$447
Best flights from Jamaica to IllinoisDiscover carefully curated flight deals from Jamaica to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
Discover carefully curated flight deals from Jamaica to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
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.
Sat 9/122:40 pm
MBJ
- ORD
1 stop29h 25m
United Airlines
Sat 9/195:45 pm
ORD
- MBJ
1 stop17h 58m
United Airlines
Deal found 7/30![United Airlines logo]()
$402
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 9/71:09 pm
MBJ
- ORD
1 stop7h 46m
Delta
Sat 9/196:00 pm
ORD
- MBJ
1 stop17h 33m
Delta
Deal found 7/29![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:50 pm
MBJ
- MDW
1 stop7h 10m
Southwest
Sat 9/195:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Deal found 8/1![Southwest logo]()
$406
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:20 pm
MBJ
- ORD
1 stop16h 03m
Air Canada
Sun 11/294:30 pm
ORD
- MBJ
1 stop23h 50m
Air Canada
Deal found 7/28![Air Canada logo]()
$425
This Orbitz deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/252:49 pm
MBJ
- MDW
1 stop20h 09m
Frontier
Sat 10/317:25 am
MDW
- MBJ
1 stop5h 59m
Frontier
Deal found 8/2![Frontier logo]()
$475
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:40 pm
KIN
- ORD
1 stop9h 28m
JetBlue
Mon 9/286:00 am
ORD
- KIN
1 stop6h 45m
JetBlue
Deal found 7/31![JetBlue logo]()
$493
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/233:20 pm
MBJ
- ORD
1 stop9h 29m
United Airlines
Sun 11/298:40 am
ORD
- MBJ
Nonstop4h 08m
United Airlines
Deal found 8/1![United Airlines logo]()
$402
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.
Sat 9/54:59 pm
MBJ
- ORD
2 stops17h 43m
Delta
Sun 9/207:30 pm
ORD
- MBJ
2 stops16h 18m
Delta
Deal found 7/29![Delta logo]()
$403
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.
Fri 9/412:52 pm
MBJ
- ORD
1 stop18h 48m
United Airlines
Fri 9/189:35 pm
ORD
- MBJ
1 stop15h 55m
United Airlines
Deal found 7/29![United Airlines logo]()
$403
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 9/32:26 pm
MBJ
- ORD
2 stops17h 30m
Delta
Mon 9/146:25 pm
ORD
- MBJ
2 stops17h 08m
Delta
Deal found 7/29![Delta logo]()
$403
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 9/132:00 pm
MBJ
- MDW
1 stop8h 30m
Southwest
Sun 9/205:00 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 7/30![Southwest logo]()
$446
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 9/71:09 pm
MBJ
- MDW
2 stops19h 58m
Delta
Mon 9/147:01 pm
MDW
- MBJ
2 stops16h 32m
Delta
Deal found 7/29![Delta logo]()
$403
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 9/21:09 pm
MBJ
- MDW
1 stop9h 27m
Delta
Sun 9/207:01 pm
MDW
- MBJ
2 stops16h 47m
Delta
Deal found 7/29![Delta logo]()
$403
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:40 pm
MBJ
- ORD
1 stop19h 35m
United Airlines
Sat 9/56:20 pm
ORD
- MBJ
1 stop17h 23m
United Airlines
Deal found 8/1![United Airlines logo]()
$444
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.
Fri 9/44:59 pm
MBJ
- MDW
2 stops16h 18m
Delta
Mon 9/146:05 am
MDW
- MBJ
1 stop6h 56m
Delta
Deal found 7/29![Delta logo]()
$403
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.
Sun 8/3012:45 pm
MBJ
- MDW
2 stops10h 10m
Southwest
Sun 9/67:45 am
MDW
- MBJ
1 stop6h 40m
Southwest
Deal found 7/31![Southwest logo]()
$566
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 9/71:09 pm
MBJ
- MDW
1 stop9h 27m
Delta
Sun 9/207:01 pm
MDW
- MBJ
2 stops16h 47m
Delta
Deal found 7/29![Delta logo]()
$403
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.
Sat 8/2211:40 am
MBJ
- MDW
1 stop8h 50m
Southwest
Mon 8/245:55 am
MDW
- MBJ
2 stops7h 20m
Southwest
Deal found 7/31![Southwest logo]()
$582
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:13 am
KIN
- ORD
2 stops11h 17m
Delta
Sat 9/198:55 am
ORD
- KIN
2 stops11h 15m
Delta
Deal found 8/2![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:13 am
KIN
- ORD
2 stops11h 17m
Delta
Mon 9/218:55 am
ORD
- KIN
2 stops11h 15m
Delta
Deal found 8/2![Delta logo]()
$511
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.
Fri 8/289:13 am
KIN
- ORD
1 stop7h 38m
Delta
Wed 9/167:05 am
ORD
- KIN
2 stops13h 05m
Delta
Deal found 7/30![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Mon 8/246:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Deal found 8/1![Delta logo]()
$531
Last-minute flights from Jamaica to IllinoisDiscover last-minute flight deals from Jamaica to Illinois. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Jamaica to Illinois. Data last updated August 2, 2026 and is based on user searches.
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.
Wed 8/195:16 pm
KIN
- ORD
1 stop7h 19m
American Airlines
Wed 9/28:37 am
ORD
- KIN
1 stop9h 49m
American Airlines
Deal found 7/29![American Airlines logo]()
$533
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 8/225:08 pm
MBJ
- ORD
1 stop14h 26m
American Airlines
Mon 8/244:00 pm
ORD
- MBJ
1 stop22h 23m
American Airlines
Deal found 7/29![American Airlines logo]()
$406
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 8/222:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Mon 8/246:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Deal found 7/28![Delta logo]()
$531
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.
Sat 8/2211:40 am
MBJ
- MDW
1 stop8h 50m
Southwest
Mon 8/247:25 am
MDW
- MBJ
1 stop5h 50m
Southwest
Deal found 7/31![Southwest logo]()
$577
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 8/255:16 pm
KIN
- ORD
1 stop16h 44m
American Airlines
Tue 9/155:00 am
ORD
- KIN
1 stop7h 04m
American Airlines
Deal found 7/30![American Airlines logo]()
$528
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:32 pm
MBJ
- ORD
1 stop18h 21m
Frontier
Thu 9/38:30 pm
ORD
- MBJ
2 stops39h 47m
Frontier
Deal found 7/28![Frontier logo]()
$518
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 8/282:00 pm
KIN
- ORD
2 stops9h 52m
American Airlines
Wed 9/165:00 am
ORD
- KIN
1 stop11h 02m
American Airlines
Deal found 7/30![American Airlines logo]()
$537
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 8/296:05 am
KIN
- ORD
1 stop17h 25m
American Airlines
Sat 9/196:00 am
ORD
- KIN
1 stop10h 02m
American Airlines
Deal found 7/29![American Airlines logo]()
$432
This Cheapflightsfares deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:08 pm
KIN
- ORD
1 stop11h 36m
JetBlue
Mon 9/216:00 am
ORD
- KIN
1 stop6h 45m
JetBlue
Deal found 8/2![JetBlue logo]()
$493
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:13 am
KIN
- ORD
1 stop9h 46m
Delta
Sat 9/197:05 am
ORD
- KIN
2 stops13h 05m
Delta
Deal found 8/2![Delta logo]()
$511
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.
Sun 8/302:52 pm
MBJ
- ORD
1 stop8h 38m
American Airlines
Sun 9/69:00 am
ORD
- MBJ
Nonstop4h 12m
American Airlines
Deal found 7/31![American Airlines logo]()
$490
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.
Sun 8/3012:45 pm
MBJ
- MDW
2 stops10h 10m
Southwest
Sun 9/67:45 am
MDW
- MBJ
1 stop6h 40m
Southwest
Deal found 7/31![Southwest logo]()
$566
One-way flights from Jamaica to IllinoisSearch for one-way flight options from Jamaica to Illinois. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
Search for one-way flight options from Jamaica to Illinois. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/23:57 pm
MBJ
- ORD
Nonstop4h 49m
American Airlines
Deal found 8/2![American Airlines logo]()
$209
This Orbitz deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/12:20 pm
MBJ
- ORD
1 stop30h 32m
Air Canada
Deal found 8/1![Air Canada logo]()
$227
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:20 pm
MBJ
- ORD
1 stop23h 18m
Air Canada
Deal found 7/31![Air Canada logo]()
$232
This Air Canada deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:20 pm
MBJ
- ORD
2 stops17h 47m
Air Canada
Deal found 8/2![Air Canada logo]()
$235
This Air Canada deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:50 pm
MBJ
- ORD
2 stops29h 30m
Air Canada
Deal found 8/1![Air Canada logo]()
$238
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.
Thu 1/283:55 pm
MBJ
- ORD
1 stop8h 47m
United Airlines
Deal found 7/29![United Airlines logo]()
$239
This Air Canada deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:50 pm
MBJ
- ORD
2 stops26h 02m
Air Canada
Deal found 8/1![Air Canada logo]()
$241
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:57 pm
MBJ
- ORD
Nonstop4h 49m
American Airlines
Deal found 8/1![American Airlines logo]()
$244
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 9/3012:59 pm
MBJ
- ORD
1 stop8h 38m
Delta
Deal found 7/29![Delta logo]()
$245
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.
Wed 10/282:26 pm
MBJ
- MDW
1 stop8h 07m
Delta
Deal found 7/30![Delta logo]()
$245
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.
Tue 9/2912:52 pm
MBJ
- ORD
1 stop24h 02m
United Airlines
Deal found 7/29![United Airlines logo]()
$248
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.
Tue 1/263:25 pm
MBJ
- MDW
2 stops18h 20m
Delta
Deal found 7/30![Delta logo]()
$248
Find flight deals from Jamaica to Illinois
Keep the following information in mind while searching for Jamaica to Illinois flight deals. Data was last updated August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $382 (FlightHub) |
One-way from | $209 (American Airlines) |
Good round-trip deal | $430 or less |
Good one-way deal | $301 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Jamaica to Illinois 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 August 2, 2026.
Use the filters below to find and compare flights from Jamaica to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 9/12
2:40 pm-8:05 pm
1 stop29h 25m
Chicago O'Hare Intl
Sat 9/19
5:45 pm-11:43 am
1 stop17h 58m
$402
Quickest round-trip
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Mon 11/23
3:20 pm-11:49 pm
1 stop9h 29m
Chicago O'Hare Intl
Sun 11/29
8:40 am-1:48 pm
Nonstop4h 08m
$402
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Mon 9/7
1:09 pm-8:55 pm
1 stop7h 46m
Chicago O'Hare Intl
Sat 9/19
6:00 pm-11:33 am
1 stop17h 33m
$403
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 9/5
4:59 pm-10:42 am
2 stops17h 43m
Chicago O'Hare Intl
Sun 9/20
7:30 pm-11:48 am
2 stops16h 18m
$403
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 9/4
12:52 pm-7:40 am
1 stop18h 48m
Chicago O'Hare Intl
Fri 9/18
9:35 pm-1:30 pm
1 stop15h 55m
$403
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 9/3
2:26 pm-7:56 am
2 stops17h 30m
Chicago O'Hare Intl
Mon 9/14
6:25 pm-11:33 am
2 stops17h 08m
$403
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Mon 9/7
1:09 pm-9:07 am
2 stops19h 58m
Chicago Midway
Mon 9/14
7:01 pm-11:33 am
2 stops16h 32m
$403
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Wed 9/2
1:09 pm-10:36 pm
1 stop9h 27m
Chicago Midway
Sun 9/20
7:01 pm-11:48 am
2 stops16h 47m
$403
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Fri 9/4
4:59 pm-9:17 am
2 stops16h 18m
Chicago Midway
Mon 9/14
6:05 am-1:01 pm
1 stop6h 56m
$403
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Mon 9/7
1:09 pm-10:36 pm
1 stop9h 27m
Chicago Midway
Sun 9/20
7:01 pm-11:48 am
2 stops16h 47m
$403
Showing 1-10 of 50 resultsSorted by cheapest first
Best time to book a flight from Jamaica to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Jamaica with our price prediction graph.
MBJ-ORD
KIN-ORD
MBJ-MDW
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 Jamaica to Illinois
JM0-USIL
MBJ-ORD
KIN-ORD
MBJ-MDW
What is the cheapest month to book a flight from Jamaica to Illinois?
Currently, September is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $348). Flying from Jamaica to Illinois in August is currently the most expensive (average of $563). 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 JM to IL?
Find hourly flight availability from Jamaica to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2026.
When flying from Jamaica to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated August 2, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Jamaica to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Related info for your journey
Find useful and relevant information for your journey from Jamaica to Illinois. 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
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Alternative routes for Jamaica to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Jamaica to Illinois by cabin class
Find flights from Jamaica to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jamaica and Illinois flights
Browse other Jamaica and Illinois flight options. Last updated on August 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Jamaica after your stay in Illinois
Jamaica to Illinois flights
Consider these flights traveling from Jamaica to Illinois.
Top 2 airlines flying from Jamaica to Illinois
Discover the top 2 airlines that operate flights from Jamaica to Illinois. 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 August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$281 | Average$431 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$281 | Average$405 | FlexibilityNo cancel fee | On-time71% |