$175+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Nov 2 — Nov 91
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Jamaica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 3, 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 3, 2026.
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 11/125:13 pm -
2 stops18h 08m
Mon 11/166:09 pm -
2 stops17h 41m
Deal found 10/2![American Airlines logo]()
$417
This Frontier deal was found by Cheapflights users on 9/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:15 am -
1 stop7h 13m
Thu 12/32:18 pm -
1 stop8h 22m
Deal found 9/30![Frontier logo]()
$442
This CheapOair deal was found by Cheapflights users on 9/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:32 pm -
1 stop16h 45m
Sat 12/126:20 pm -
2 stops14h 40m
Deal found 9/29![Multiple Airlines logo]()
$445
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
1 stop8h 12m
Sat 10/173:48 pm -
1 stop7h 55m
Deal found 9/30![Frontier logo]()
$447
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop7h 13m
Tue 11/242:01 pm -
1 stop10h 17m
Deal found 9/30![Frontier logo]()
$448
This Orbitz deal was found by Cheapflights users on 9/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:31 am -
1 stop28h 25m
Sun 11/222:20 pm -
1 stop30h 32m
Deal found 9/28![Multiple Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/315:29 pm -
1 stop16h 46m
Tue 11/32:12 pm -
1 stop18h 15m
Deal found 9/29![American Airlines logo]()
$450
This Priceline deal was found by Cheapflights users on 10/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:50 pm -
1 stop18h 18m
Sun 11/12:20 pm -
2 stops18h 34m
Deal found 10/2![Multiple Airlines logo]()
$452
This FlightHub deal was found by Cheapflights users on 9/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:42 pm -
1 stop19h 46m
Mon 11/94:23 pm -
1 stop8h 24m
Deal found 9/30![Frontier logo]()
$453
This FlightHub deal was found by Cheapflights users on 9/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:50 pm -
1 stop18h 18m
Sun 11/84:43 pm -
1 stop17h 34m
Deal found 9/30![Frontier logo]()
$453
This FlightHub deal was found by Cheapflights users on 10/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:42 pm -
1 stop19h 47m
Sat 11/144:43 pm -
1 stop8h 04m
Deal found 10/1![Frontier logo]()
$454
This FlightHub deal was found by Cheapflights users on 9/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:44 pm -
1 stop18h 49m
Sat 10/313:50 pm -
1 stop18h 06m
Deal found 9/30![Frontier logo]()
$454
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 3, 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 3, 2026.
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 11/125:13 pm -
2 stops18h 08m
Mon 11/166:09 pm -
2 stops17h 41m
Deal found 10/2![American Airlines logo]()
$417
This Copa Airlines deal was found by Cheapflights users on 10/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/202:13 pm -
1 stop20h 02m
Sat 2/272:28 pm -
1 stop10h 43m
Deal found 10/1![Copa Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:52 am -
1 stop6h 27m
Tue 12/82:54 pm -
Nonstop4h 26m
Deal found 10/2![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 9/29. 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 1/165:25 pm -
1 stop16h 45m
Wed 1/204:10 pm -
1 stop17h 39m
Deal found 9/29![Delta logo]()
$483
This Southwest deal was found by Cheapflights users on 9/28. 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 2/66:45 am -
1 stop7h 15m
Thu 2/112:00 pm -
1 stop10h 05m
Deal found 9/28![Southwest logo]()
$544
This Air Canada deal was found by Cheapflights users on 10/2. 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.
Tue 10/209:55 am -
1 stop28h 00m
Thu 10/222:35 pm -
2 stops41h 09m
Deal found 10/2![Air Canada logo]()
$843
This Mytrip deal was found by Cheapflights users on 10/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:29 am -
3 stops31h 16m
Mon 11/169:10 am -
3 stops34h 20m
Deal found 10/2![Multiple Airlines logo]()
$845
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Sat 1/165:44 pm -
2 stops19h 51m
Sun 1/243:35 pm -
2 stops20h 36m
Deal found 10/2![American Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 9/29. 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 1/165:55 pm -
1 stop16h 15m
Wed 1/204:10 pm -
1 stop17h 33m
Deal found 9/29![Delta logo]()
$483
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 1/107:00 pm -
2 stops16h 13m
Sat 1/162:54 pm -
1 stop9h 26m
Deal found 9/30![United Airlines logo]()
$512
This Delta deal was found by Cheapflights users on 9/30. 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 10/2712:49 pm -
2 stops22h 41m
Fri 12/46:12 pm -
2 stops16h 25m
Deal found 9/30![Delta logo]()
$487
This Copa Airlines deal was found by Cheapflights users on 10/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:13 pm -
1 stop22h 39m
Sun 11/222:58 pm -
1 stop10h 13m
Deal found 10/1![Copa Airlines logo]()
$536
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 11/115:13 pm -
1 stop22h 56m
Sat 11/146:09 pm -
2 stops17h 50m
Deal found 9/28![American Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:25 am -
1 stop7h 30m
Sun 12/63:45 pm -
2 stops9h 20m
Deal found 10/2![Southwest logo]()
$565
This Delta deal was found by Cheapflights users on 9/30. 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 10/2712:49 pm -
2 stops22h 41m
Thu 12/32:19 pm -
1 stop9h 35m
Deal found 9/30![Delta logo]()
$487
This United Airlines deal was found by Cheapflights users on 9/29. 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 11/128:40 am -
Nonstop4h 08m
Mon 11/162:54 pm -
Nonstop4h 26m
Deal found 9/29![United Airlines logo]()
$538
This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 2/123:58 pm -
2 stops19h 26m
Mon 2/224:29 pm -
2 stops22h 28m
Deal found 10/3![American Airlines logo]()
$503
This Copa Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 11/132:13 pm -
1 stop22h 39m
Fri 11/202:58 pm -
1 stop10h 13m
Deal found 9/29![Copa Airlines logo]()
$556
This Delta deal was found by Cheapflights users on 9/29. 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 11/96:49 am -
1 stop6h 14m
Thu 11/196:12 pm -
2 stops14h 37m
Deal found 9/29![Delta logo]()
$487
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Wed 3/178:42 am -
Nonstop4h 04m
Mon 3/221:48 pm -
Nonstop4h 28m
Deal found 9/30![United Airlines logo]()
$541
This Southwest deal was found by Cheapflights users on 9/28. 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.
Wed 1/136:25 am -
1 stop6h 45m
Sat 1/161:25 pm -
Nonstop4h 05m
Deal found 9/28![Southwest logo]()
$623
This Copa Airlines deal was found by Cheapflights users on 10/2. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/112:13 pm -
1 stop20h 06m
Sun 1/1712:18 pm -
1 stop25h 28m
Deal found 10/2![Copa Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 9/28. 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.
Mon 1/46:00 am -
1 stop5h 55m
Fri 1/154:50 pm -
2 stops16h 55m
Deal found 9/28![Delta logo]()
$488
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 2/12:31 pm -
2 stops20h 42m
Fri 2/53:20 pm -
2 stops24h 50m
Deal found 9/28![United Airlines logo]()
$548
This Southwest deal was found by Cheapflights users on 10/1. 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.
Fri 12/115:05 am -
2 stops8h 40m
Mon 12/141:50 pm -
2 stops9h 50m
Deal found 10/1![Southwest logo]()
$625
This Copa Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 3/253:13 pm -
1 stop19h 57m
Thu 4/112:19 pm -
1 stop12h 25m
Deal found 9/29![Copa Airlines logo]()
$573
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Sun 1/316:10 pm -
1 stop16h 59m
Wed 2/312:49 pm -
1 stop12h 10m
Deal found 9/28![American Airlines logo]()
$587
This Copa Airlines deal was found by Cheapflights users on 9/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:13 pm -
1 stop22h 39m
Thu 11/122:58 pm -
1 stop10h 13m
Deal found 9/28![Copa Airlines logo]()
$585
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Sat 11/77:50 pm -
1 stop15h 11m
Thu 11/1212:41 pm -
1 stop13h 03m
Deal found 10/2![American Airlines logo]()
$587
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/258:20 pm -
2 stops17h 40m
Mon 3/11:10 pm -
2 stops10h 50m
Deal found 10/2![Southwest logo]()
$646
Last-minute flights from Illinois to JamaicaDiscover last-minute flight deals from Illinois to Jamaica. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Jamaica. Data last updated October 3, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
1 stop8h 12m
Sat 10/173:48 pm -
1 stop7h 55m
Deal found 9/30![Frontier logo]()
$447
This FlightHub deal was found by Cheapflights users on 9/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:44 pm -
1 stop18h 49m
Sat 10/313:50 pm -
1 stop18h 06m
Deal found 9/30![Frontier logo]()
$454
This Priceline deal was found by Cheapflights users on 10/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:50 pm -
1 stop18h 18m
Sun 11/12:20 pm -
2 stops18h 34m
Deal found 10/2![Multiple Airlines logo]()
$452
This Frontier deal was found by Cheapflights users on 9/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:15 am -
1 stop7h 13m
Thu 12/32:18 pm -
1 stop8h 22m
Deal found 9/30![Frontier logo]()
$442
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/315:29 pm -
1 stop16h 46m
Tue 11/32:12 pm -
1 stop18h 15m
Deal found 9/29![American Airlines logo]()
$450
This FlightHub deal was found by Cheapflights users on 9/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:50 pm -
1 stop18h 18m
Sun 11/84:43 pm -
1 stop17h 34m
Deal found 9/30![Frontier logo]()
$453
This FlightHub deal was found by Cheapflights users on 9/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:42 pm -
1 stop19h 46m
Mon 11/94:23 pm -
1 stop8h 24m
Deal found 9/30![Frontier logo]()
$453
This Justfly.com deal was found by Cheapflights users on 9/30. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
1 stop7h 13m
Sun 11/154:43 pm -
1 stop17h 34m
Deal found 9/30![Frontier logo]()
$445
This FlightHub deal was found by Cheapflights users on 10/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:42 pm -
1 stop19h 47m
Sat 11/144:43 pm -
1 stop8h 04m
Deal found 10/1![Frontier logo]()
$454
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 11/125:13 pm -
2 stops18h 08m
Mon 11/166:09 pm -
2 stops17h 41m
Deal found 10/2![American Airlines logo]()
$417
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop7h 13m
Tue 11/242:01 pm -
1 stop10h 17m
Deal found 9/30![Frontier logo]()
$448
This Orbitz deal was found by Cheapflights users on 9/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:31 am -
1 stop28h 25m
Sun 11/222:20 pm -
1 stop30h 32m
Deal found 9/28![Multiple Airlines logo]()
$449
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 3, 2026.
Search for one-way flight options from Illinois to Jamaica. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:16 am -
1 stop7h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 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 9/29![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 9/30. 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 Frontier 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 9/30![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 9/30. 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 Frontier 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 9/30![Frontier logo]()
$177
This CheapOair deal was found by Cheapflights users on 9/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:16 am -
1 stop7h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$179
This FlightHub deal was found by Cheapflights users on 10/2. 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.
Fri 12/410:37 pm -
1 stop13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$179
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 1/37:18 pm -
1 stop17h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 9/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$187
This CheapOair deal was found by Cheapflights users on 9/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:15 am -
1 stop8h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$189
This FlightHub deal was found by Cheapflights users on 10/2. 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.
Thu 12/310:37 pm -
1 stop13h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$189
This CheapOair deal was found by Cheapflights users on 10/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop8h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$191
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 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $417 (American Airlines) |
One-way from | $175 (Cheapflightsfares) |
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 3, 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
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
Tue 1/12
8:40 am-1:48 pm
Nonstop4h 08m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
Quickest round-trip
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Tue 3/16
8:42 am-12:46 pm
Nonstop4h 04m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 1/12
6:00 am-3:25 pm
1 stop8h 25m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 1/19
5:45 am-1:00 pm
1 stop6h 15m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Fri 1/1
6:00 am-9:10 pm
1 stop14h 10m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Thu 12/31
6:00 am-12:56 pm
1 stop5h 56m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sat 12/5
5:30 pm-12:27 pm
2 stops17h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Fri 10/23
9:45 pm-1:30 pm
1 stop15h 45m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Thu 3/25
7:55 pm-10:05 am
1 stop14h 10m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from Illinois to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Illinois with our price prediction graph.
MDW-MBJ
ORD-MBJ
MLI-MBJ
ORD-KIN
BMI-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Illinois to Jamaica
USIL-JM0
MDW-MBJ
ORD-MBJ
MLI-MBJ
ORD-KIN
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 $480). Flying from Illinois to Jamaica in December is currently the most expensive (average of $660). 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 64 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.
Alternative routes
Complete your 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 3, 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 3, 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$616 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$302 | Average$575 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$314 | Average$611 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |