$158+ Cheap flights from Illinois to Jamaica
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Nov 9 — Nov 161
Round-trip
1 adult, Economy
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Cheapest flights from Illinois to JamaicaExplore the most affordable flight options available from Illinois to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
Explore the most affordable flight options available from Illinois to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/34:04 pm -
2 stops21h 23m
Mon 12/76:09 pm -
2 stops20h 39m
Deal found 10/9![American Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop10h 12m
Sun 11/13:59 pm -
Nonstop4h 47m
Deal found 10/6![American Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:50 pm -
1 stop15h 31m
Sat 11/141:10 pm -
1 stop10h 20m
Deal found 10/7![American Airlines logo]()
$449
This Orbitz deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:30 pm -
1 stop23h 50m
Sat 12/52:22 pm -
1 stop17h 58m
Deal found 10/6![Multiple Airlines logo]()
$450
This FlightHub deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:00 am -
2 stops28h 13m
Mon 12/72:22 pm -
1 stop8h 20m
Deal found 10/6![Frontier logo]()
$451
This CheapOair deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:05 am -
1 stop7h 23m
Mon 11/236:20 pm -
2 stops14h 40m
Deal found 10/8![Multiple Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:08 pm -
2 stops17h 22m
Wed 11/186:12 pm -
1 stop15h 29m
Deal found 10/8![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:31 pm -
1 stop18h 32m
Wed 11/251:45 pm -
1 stop10h 46m
Deal found 10/7![American Airlines logo]()
$454
This CheapOair deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/410:37 pm -
1 stop13h 40m
Mon 12/76:20 pm -
2 stops14h 40m
Deal found 10/7![Multiple Airlines logo]()
$455
This Air Canada deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:40 pm -
1 stop20h 45m
Mon 11/236:20 pm -
2 stops17h 47m
Deal found 10/6![Air Canada logo]()
$456
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:05 pm -
1 stop17h 16m
Thu 11/123:56 pm -
Nonstop4h 50m
Deal found 10/8![American Airlines logo]()
$457
This Air Canada deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:30 pm -
1 stop23h 50m
Mon 11/166:20 pm -
1 stop16h 03m
Deal found 10/6![Air Canada logo]()
$458
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 October 10, 2026.
Discover carefully curated flight deals from Illinois to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/34:04 pm -
2 stops21h 23m
Mon 12/76:09 pm -
2 stops20h 39m
Deal found 10/9![American Airlines logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:13 pm -
1 stop20h 05m
Sun 11/812:17 pm -
1 stop12h 54m
Deal found 10/8![Copa Airlines logo]()
$468
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:40 am -
Nonstop4h 08m
Wed 12/22:54 pm -
Nonstop4h 26m
Deal found 10/9![United Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:40 pm -
2 stops16h 45m
Thu 11/53:45 pm -
2 stops9h 25m
Deal found 10/6![Southwest logo]()
$507
This JetBlue deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:00 am -
1 stop5h 55m
Wed 12/22:45 pm -
1 stop9h 48m
Deal found 10/9![JetBlue logo]()
$523
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/65:55 pm -
1 stop16h 15m
Tue 1/123:25 pm -
1 stop19h 08m
Deal found 10/9![Delta logo]()
$598
This Priceline deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:20 pm -
2 stops25h 48m
Mon 11/164:23 pm -
1 stop8h 24m
Deal found 10/9![Frontier logo]()
$649
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/165:44 pm -
2 stops19h 51m
Sun 1/243:35 pm -
2 stops20h 36m
Deal found 10/8![American Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/12:26 pm -
1 stop22h 22m
Fri 2/52:54 pm -
1 stop9h 30m
Deal found 10/5![United Airlines logo]()
$490
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/36:07 pm -
1 stop19h 45m
Sat 4/102:29 pm -
2 stops21h 18m
Deal found 10/9![American Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop7h 25m
Wed 12/91:50 pm -
2 stops8h 40m
Deal found 10/6![Southwest logo]()
$517
This Copa Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:13 pm -
1 stop22h 39m
Wed 11/112:58 pm -
1 stop10h 13m
Deal found 10/7![Copa Airlines logo]()
$536
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/75:55 am -
1 stop7h 19m
Wed 1/132:54 pm -
Nonstop4h 26m
Deal found 10/9![United Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/254:11 pm -
1 stop17h 01m
Thu 3/44:00 pm -
1 stop9h 08m
Deal found 10/7![American Airlines logo]()
$489
This Copa Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:13 pm -
1 stop20h 05m
Sun 11/812:17 pm -
1 stop25h 29m
Deal found 10/7![Copa Airlines logo]()
$551
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:20 am -
1 stop8h 25m
Wed 12/231:50 pm -
1 stop7h 55m
Deal found 10/9![Southwest logo]()
$557
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 am -
Nonstop4h 08m
Sat 11/142:54 pm -
Nonstop4h 26m
Deal found 10/6![United Airlines logo]()
$544
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/65:45 am -
1 stop6h 15m
Tue 1/123:10 pm -
1 stop7h 10m
Deal found 10/9![Southwest logo]()
$588
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:13 am -
1 stop28h 35m
Sat 11/72:54 pm -
1 stop7h 28m
Deal found 10/6![United Airlines logo]()
$549
This KAYAK deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/152:13 pm -
1 stop22h 39m
Fri 11/202:58 pm -
1 stop10h 13m
Deal found 10/6![Copa Airlines logo]()
$626
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/123:56 pm -
2 stops19h 26m
Sun 2/216:03 pm -
2 stops22h 17m
Deal found 10/6![American Airlines logo]()
$583
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:00 am -
1 stop6h 45m
Wed 12/163:25 pm -
1 stop7h 00m
Deal found 10/6![Southwest logo]()
$611
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:05 am -
2 stops11h 55m
Sun 11/229:00 am -
2 stops12h 17m
Deal found 10/9![Delta logo]()
$825
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:40 am -
Nonstop4h 08m
Thu 10/292:01 pm -
Nonstop4h 26m
Deal found 10/6![United Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:50 pm -
1 stop15h 11m
Thu 11/1212:41 pm -
1 stop13h 03m
Deal found 10/5![American Airlines logo]()
$587
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:00 am -
1 stop8h 30m
Tue 12/153:25 pm -
1 stop7h 00m
Deal found 10/6![Southwest logo]()
$621
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:09 am -
2 stops9h 06m
Sat 10/319:15 am -
1 stop11h 23m
Deal found 10/5![Delta logo]()
$859
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:40 am -
Nonstop4h 08m
Mon 11/92:54 pm -
Nonstop4h 26m
Deal found 10/5![United Airlines logo]()
$591
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:25 pm -
2 stops15h 25m
Mon 11/91:50 pm -
2 stops10h 25m
Deal found 10/5![Southwest logo]()
$625
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:09 am -
2 stops9h 06m
Tue 11/39:15 am -
1 stop12h 23m
Deal found 10/5![Delta logo]()
$859
Last-minute flights from Illinois to JamaicaDiscover last-minute flight deals from Illinois to Jamaica. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Jamaica. Data last updated October 10, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:03 am -
1 stop28h 47m
Sat 10/313:50 pm -
1 stop18h 10m
Deal found 10/6![Multiple Airlines logo]()
$462
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop10h 12m
Sun 11/13:59 pm -
Nonstop4h 47m
Deal found 10/6![American Airlines logo]()
$448
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:55 am -
1 stop7h 19m
Wed 11/42:54 pm -
Nonstop4h 26m
Deal found 10/8![United Airlines logo]()
$460
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:05 pm -
1 stop17h 16m
Thu 11/123:56 pm -
Nonstop4h 50m
Deal found 10/8![American Airlines logo]()
$457
This FlightHub deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:42 pm -
1 stop19h 26m
Sun 11/84:43 pm -
1 stop26h 04m
Deal found 10/9![Frontier logo]()
$462
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:23 pm -
2 stops22h 07m
Fri 11/136:12 pm -
1 stop6h 42m
Deal found 10/8![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:50 pm -
1 stop15h 31m
Sat 11/141:10 pm -
1 stop10h 20m
Deal found 10/7![American Airlines logo]()
$449
This Expedia deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:08 am -
1 stop8h 00m
Mon 11/164:23 pm -
1 stop8h 24m
Deal found 10/6![Frontier logo]()
$461
This Air Canada deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:30 pm -
1 stop23h 50m
Mon 11/166:20 pm -
1 stop16h 03m
Deal found 10/6![Air Canada logo]()
$458
This CheapOair deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:05 am -
1 stop7h 23m
Mon 11/236:20 pm -
2 stops14h 40m
Deal found 10/8![Multiple Airlines logo]()
$452
This Air Canada deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:40 pm -
1 stop20h 45m
Mon 11/236:20 pm -
2 stops17h 47m
Deal found 10/6![Air Canada logo]()
$456
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:31 pm -
1 stop18h 32m
Wed 11/251:45 pm -
1 stop10h 46m
Deal found 10/7![American Airlines logo]()
$454
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 October 10, 2026.
Search for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This JetBlue deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:00 am -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![JetBlue logo]()
$158
This JetBlue deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$159
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 am -
1 stop10h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![American Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:27 am -
1 stop7h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:04 am -
1 stop9h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$167
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/66:00 am -
1 stop10h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:40 am -
Nonstop4h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![American Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:30 pm -
2 stops20h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$173
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:05 am -
2 stops8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop7h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:15 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$175
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 October 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $438 (American Airlines) |
One-way from | $158 (JetBlue) |
Popular in | December |
Cheapest in | September |
Average price | $572 |
Good round-trip deal | $553 or less |
Good one-way deal | $250 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 7,457,451 searches. Data last updated October 10, 2026.
Use the filters below to find and compare flights from Illinois to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 11/8
7:00 am-2:57 pm
1 stop6h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 11/9
7:00 am-2:57 pm
1 stop6h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 11/16
7:05 am-4:57 pm
2 stops8h 52m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 12/7
6:49 am-4:57 pm
1 stop9h 08m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 11/10
6:00 am-4:57 pm
1 stop9h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 11/9
6:08 am-3:08 pm
1 stop8h 00m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
MolineMontego Bay
MLI Moline Quad-City - MBJ Montego Bay Sangster Intl
MLIMBJ
Moline Quad-City
Sun 1/3
7:18 pm-2:14 pm
2 stops17h 56m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 11/8
7:30 pm-4:57 pm
2 stops20h 27m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$183
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 11/9
7:15 pm-12:51 pm
2 stops16h 36m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$183
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 11/9
6:44 pm-4:57 pm
2 stops21h 13m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$183
Showing 1-10 of 59 resultsSorted by cheapest first
Best time to book a flight from Illinois to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Illinois with our price prediction graph.
ORD-MBJ
MDW-MBJ
BMI-MBJ
MLI-MBJ
ORD-KIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Illinois to Jamaica
USIL-JM0
ORD-MBJ
MDW-MBJ
BMI-MBJ
MLI-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 $474). Flying from Illinois to Jamaica in December is currently the most expensive (average of $670). 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.
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 58 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 October 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Jamaica
Find the right flight back to Illinois after your stay in Jamaica
Illinois to Jamaica flights
Consider these flights traveling from Illinois to Jamaica.
Top 6 airlines flying from Illinois to Jamaica
Discover the top 6 airlines that operate flights from Illinois to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$592 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$493 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$301 | Average$575 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$302 | Average$591 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$611 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$467 | Average$660 | FlexibilityNo cancel fee | On-time63% |