$209+ Cheap flights from Jamaica to Chicago (CHI)
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 — CHI
Sep 3 — Sep 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Jamaica to Chicago 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Jamaica to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Jamaica to ChicagoExplore the most affordable flight options available from Jamaica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
Explore the most affordable flight options available from Jamaica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 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 -
1 stop21h 47m
Sat 10/315:54 pm -
1 stop19h 31m
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 -
1 stop16h 03m
Sun 11/294:30 pm -
1 stop23h 50m
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 -
Nonstop4h 43m
Tue 9/89:00 am -
Nonstop4h 12m
Deal found 8/2![American Airlines logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 -
1 stop9h 29m
Sun 11/298:40 am -
Nonstop4h 08m
Deal found 8/4![United Airlines logo]()
$402
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 9/122:40 pm -
1 stop29h 25m
Sat 9/195:45 pm -
1 stop17h 58m
Deal found 8/1![United Airlines 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 9/121:50 pm -
1 stop7h 10m
Sat 9/195:55 am -
1 stop6h 30m
Deal found 7/31![Southwest logo]()
$406
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.
Sat 8/225:08 pm -
1 stop14h 26m
Mon 8/244:00 pm -
1 stop22h 23m
Deal found 8/2![American Airlines logo]()
$409
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 -
2 stops14h 42m
Mon 9/285:20 am -
2 stops7h 33m
Deal found 7/31![American Airlines logo]()
$411
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 -
1 stop9h 49m
Mon 9/77:00 am -
1 stop10h 18m
Deal found 7/31![JetBlue logo]()
$447
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:40 pm -
1 stop9h 28m
Sun 9/276:00 am -
1 stop6h 45m
Deal found 8/2![JetBlue logo]()
$448
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:15 pm -
1 stop8h 30m
Wed 9/306:30 am -
1 stop6h 25m
Deal found 8/3![Southwest logo]()
$459
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 -
1 stop20h 09m
Sat 10/317:25 am -
1 stop5h 59m
Deal found 8/2![Frontier logo]()
$475
Best flights from Jamaica to ChicagoDiscover carefully curated flight deals from Jamaica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
Discover carefully curated flight deals from Jamaica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
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 11/236:20 pm -
2 stops17h 47m
Sun 11/295:58 pm -
2 stops22h 22m
Deal found 8/2![Air Canada logo]()
$394
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/233:20 pm -
1 stop9h 29m
Sun 11/298:40 am -
Nonstop4h 08m
Deal found 8/3![United Airlines logo]()
$402
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.
Tue 10/205:13 pm -
1 stop7h 25m
Tue 11/106:05 pm -
1 stop15h 10m
Deal found 8/2![American Airlines logo]()
$406
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 -
1 stop7h 10m
Sat 9/195:55 am -
1 stop6h 30m
Deal found 8/1![Southwest logo]()
$406
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:08 pm -
1 stop11h 36m
Mon 9/216:00 am -
1 stop6h 45m
Deal found 8/1![JetBlue logo]()
$493
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:57 pm -
1 stop10h 05m
Mon 9/73:20 pm -
1 stop22h 31m
Deal found 8/3![Copa Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:13 am -
1 stop14h 44m
Mon 9/217:05 am -
2 stops13h 05m
Deal found 8/3![Delta logo]()
$511
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 9/122:40 pm -
1 stop29h 25m
Sat 9/195:45 pm -
1 stop17h 58m
Deal found 8/1![United Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:15 pm -
1 stop8h 30m
Wed 9/306:30 am -
1 stop6h 25m
Deal found 8/3![Southwest logo]()
$459
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.
Sat 8/225:08 pm -
1 stop14h 26m
Mon 8/248:53 pm -
1 stop14h 44m
Deal found 7/31![American Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:52 pm -
1 stop10h 29m
Wed 9/306:00 am -
1 stop29h 43m
Deal found 8/3![United Airlines logo]()
$444
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 -
1 stop9h 28m
Mon 9/286:00 am -
1 stop6h 45m
Deal found 7/31![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.
Thu 10/19:10 am -
2 stops9h 16m
Thu 10/158:29 am -
2 stops11h 46m
Deal found 8/2![Delta logo]()
$511
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 -
1 stop19h 35m
Sat 9/56:20 pm -
1 stop17h 23m
Deal found 8/1![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:13 am -
1 stop9h 46m
Sat 9/197:05 am -
2 stops13h 05m
Deal found 8/3![Delta logo]()
$511
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:55 pm -
1 stop6h 50m
Tue 9/86:30 am -
1 stop6h 25m
Deal found 8/2![Southwest logo]()
$529
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:10 am -
1 stop9h 35m
Wed 9/306:40 am -
1 stop13h 30m
Deal found 8/3![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:15 am -
1 stop8h 48m
Sun 11/157:00 am -
2 stops11h 00m
Deal found 8/3![Delta logo]()
$511
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 -
2 stops10h 10m
Sun 9/67:45 am -
1 stop6h 40m
Deal found 7/31![Southwest logo]()
$566
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:52 pm -
1 stop10h 30m
Wed 9/96:10 pm -
1 stop17h 33m
Deal found 8/3![United Airlines logo]()
$547
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:26 pm -
1 stop8h 10m
Mon 8/246:05 am -
1 stop9h 29m
Deal found 8/3![Delta logo]()
$531
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:50 pm -
1 stop7h 05m
Mon 8/245:55 am -
2 stops7h 20m
Deal found 8/2![Southwest logo]()
$616
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.
Tue 10/202:26 pm -
1 stop8h 07m
Tue 11/106:00 am -
1 stop7h 15m
Deal found 8/2![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/212:26 pm -
1 stop8h 10m
Mon 8/246:05 am -
1 stop9h 29m
Deal found 8/4![Delta logo]()
$587
Last-minute flights from Jamaica to ChicagoDiscover last-minute flight deals from Jamaica to Chicago. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Jamaica to Chicago. Data last updated August 4, 2026 and is based on user searches.
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.
Sat 8/225:08 pm -
1 stop14h 26m
Mon 8/244:00 pm -
1 stop22h 23m
Deal found 8/2![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:59 pm -
1 stop6h 58m
Mon 8/245:30 am -
1 stop10h 04m
Deal found 8/3![Delta logo]()
$463
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 -
1 stop19h 35m
Sat 9/56:20 pm -
1 stop17h 23m
Deal found 8/1![United Airlines logo]()
$444
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:08 pm -
1 stop11h 36m
Mon 9/216:00 am -
1 stop6h 45m
Deal found 8/1![JetBlue logo]()
$493
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 -
Nonstop4h 43m
Tue 9/89:00 am -
Nonstop4h 12m
Deal found 8/2![American Airlines logo]()
$391
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 -
1 stop9h 49m
Mon 9/77:00 am -
1 stop10h 18m
Deal found 7/31![JetBlue logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:57 pm -
1 stop10h 05m
Mon 9/73:20 pm -
1 stop22h 31m
Deal found 8/3![Copa Airlines logo]()
$499
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 9/122:40 pm -
1 stop29h 25m
Sat 9/195:45 pm -
1 stop17h 58m
Deal found 8/1![United Airlines 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 9/121:50 pm -
1 stop7h 10m
Sat 9/195:55 am -
1 stop6h 30m
Deal found 7/31![Southwest logo]()
$406
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:40 pm -
1 stop9h 28m
Sun 9/276:00 am -
1 stop6h 45m
Deal found 8/2![JetBlue logo]()
$448
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 -
2 stops14h 42m
Mon 9/285:20 am -
2 stops7h 33m
Deal found 7/31![American Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:15 pm -
1 stop8h 30m
Wed 9/306:30 am -
1 stop6h 25m
Deal found 8/3![Southwest logo]()
$459
One-way flights from Jamaica to ChicagoSearch for one-way flight options from Jamaica to Chicago. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
Search for one-way flight options from Jamaica to Chicago. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
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.
Mon 11/23:57 pm -
Nonstop4h 49m
Deal found 8/1![American Airlines logo]()
$209
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.
Wed 9/231:00 pm -
1 stop11h 33m
Deal found 8/1![American Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 10/1712:26 pm -
2 stops11h 18m
Deal found 8/4![American Airlines logo]()
$224
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 -
1 stop30h 32m
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 -
1 stop23h 18m
Deal found 7/31![Air Canada logo]()
$232
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.
Mon 11/26:20 pm -
2 stops17h 47m
Deal found 8/1![Air Canada logo]()
$235
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:50 pm -
1 stop20h 54m
Deal found 7/31![Air Canada logo]()
$238
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/293:55 pm -
1 stop8h 47m
Deal found 7/31![United Airlines logo]()
$239
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 -
Nonstop4h 49m
Deal found 8/1![American Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 -
1 stop8h 38m
Deal found 8/4![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:26 pm -
1 stop8h 10m
Deal found 8/3![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:50 pm -
2 stops19h 49m
Deal found 8/3![Delta logo]()
$248
Find flight deals from Jamaica to Chicago
Keep the following information in mind while searching for Jamaica to Chicago flight deals. Data was last updated August 4, 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 Chicago 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 4, 2026.
Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Mon 11/23
6:20 pm-11:07 am
2 stops17h 47m
Chicago O'Hare Intl
Sun 11/29
5:58 pm-5:20 pm
2 stops22h 22m
$394
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
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
$403
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Tue 10/20
5:13 pm-12:38 am
1 stop7h 25m
Chicago O'Hare Intl
Tue 11/10
6:05 pm-10:15 am
1 stop15h 10m
$406
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Sat 9/12
1:50 pm-9:00 pm
1 stop7h 10m
Chicago Midway
Sat 9/19
5:55 am-12:25 pm
1 stop6h 30m
$406
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 9/25
12:52 pm-11:21 pm
1 stop10h 29m
Chicago O'Hare Intl
Wed 9/30
6:00 am-11:43 am
1 stop29h 43m
$444
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 8/29
2:40 pm-10:15 am
1 stop19h 35m
Chicago O'Hare Intl
Sat 9/5
6:20 pm-11:43 am
1 stop17h 23m
$444
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Fri 9/25
2:15 pm-10:45 pm
1 stop8h 30m
Chicago Midway
Wed 9/30
6:30 am-12:55 pm
1 stop6h 25m
$459
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 8/22
5:08 pm-7:34 am
1 stop14h 26m
Chicago O'Hare Intl
Mon 8/24
8:53 pm-11:37 am
1 stop14h 44m
$463
KingstonChicago
KIN - ORD
KINORD
Kingston Norman Manley
Sat 8/29
12:08 pm-11:44 pm
1 stop11h 36m
Chicago O'Hare Intl
Mon 9/21
6:00 am-12:45 pm
1 stop6h 45m
$493
Showing 1-10 of 52 resultsSorted by cheapest first
Best time to book a flight from Jamaica to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Jamaica with our price prediction graph.
MBJ-ORD
MBJ-MDW
KIN-ORD
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 Chicago
JM0-CHI
MBJ-ORD
MBJ-MDW
KIN-ORD
What is the cheapest month to book a flight from Jamaica to Chicago?
Currently, September is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $348). Flying from Jamaica to Chicago 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 CHI?
Find hourly flight availability from Jamaica to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 4, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Jamaica to Chicago as you normally would.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 4, 2026.
Peruse reviews from past customers who have flown with American Airlines from Jamaica to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.5
Food
6.4
Entertainment
6.8
Crew
7.9
Overall
7.1
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Boarding
7.5
Food
6.4
Entertainment
6.8
Crew
7.9
Overall
7.1
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Related info for your journey
Find useful and relevant information for your journey from Jamaica to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Jamaica to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 4, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Jamaica to Chicago by cabin class
Find flights from Jamaica to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jamaica and Chicago flights
Browse other Jamaica and Chicago flight options. Last updated on August 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Jamaica to Chicago
Discover the top 2 airlines that operate flights from Jamaica to Chicago. 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 4, 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% |