$199+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Jul 18 — Jul 251
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 June 18, 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 June 18, 2026.
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/12:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Sat 11/78:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Deal found 6/14![United Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/12:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Mon 11/98:00 pm
ORD
- MBJ
1 stop15h 07m
United Airlines
Deal found 6/14![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/161:32 pm
MBJ
- ORD
1 stop6h 48m
Delta
Mon 10/197:10 am
ORD
- MBJ
1 stop6h 10m
Delta
Deal found 6/16![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/161:32 pm
MBJ
- MDW
1 stop8h 38m
Delta
Mon 10/196:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Deal found 6/16![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 11/232:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Sun 11/298:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Deal found 6/16![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/55:59 pm
MBJ
- ORD
2 stops15h 01m
Delta
Fri 11/137:40 pm
ORD
- MBJ
1 stop17h 55m
Delta
Deal found 6/14![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/55:59 pm
MBJ
- MDW
2 stops19h 34m
Delta
Sun 11/86:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Deal found 6/14![Delta logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/31:55 pm
MBJ
- ORD
1 stop10h 45m
American Airlines
Tue 11/105:00 am
ORD
- MBJ
1 stop6h 42m
American Airlines
Deal found 6/14![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/133:23 pm
MBJ
- ORD
1 stop8h 21m
American Airlines
Mon 8/179:00 am
ORD
- MBJ
Nonstop4h 12m
American Airlines
Deal found 6/17![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 9/75:08 pm
MBJ
- ORD
1 stop14h 26m
American Airlines
Mon 9/285:20 am
ORD
- MBJ
2 stops7h 33m
American Airlines
Deal found 6/17![American Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/134:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Mon 8/175:30 am
ORD
- MBJ
1 stop6h 14m
Delta
Deal found 6/14![Delta logo]()
$359
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/23:59 pm
MBJ
- ORD
1 stop8h 45m
JetBlue
Mon 11/97:00 am
ORD
- MBJ
1 stop6h 54m
JetBlue
Deal found 6/14![JetBlue logo]()
$362
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 June 18, 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 June 18, 2026.
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 11/232:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Sun 11/298:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Deal found 6/15![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/161:32 pm
MBJ
- ORD
1 stop6h 48m
Delta
Mon 10/197:10 am
ORD
- MBJ
1 stop6h 10m
Delta
Deal found 6/16![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/132:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Mon 8/179:00 am
ORD
- MBJ
Nonstop4h 12m
American Airlines
Deal found 6/17![American Airlines logo]()
$399
This Copa Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/1412:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Mon 8/243:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Deal found 6/17![Copa Airlines logo]()
$436
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Sat 8/11:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Sat 8/86:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/16![Frontier logo]()
$455
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/1612:00 pm
MBJ
- MDW
2 stops8h 25m
Southwest
Mon 10/195:10 am
MDW
- MBJ
1 stop8h 15m
Southwest
Deal found 6/16![Southwest logo]()
$492
This Justfly.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
Tue 9/16:00 am
KIN
- ORD
1 stop7h 39m
JetBlue
Tue 9/16:27 pm
ORD
- KIN
1 stop29h 20m
JetBlue
Deal found 6/13![JetBlue logo]()
$509
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/41:50 pm
MBJ
- ORD
1 stop8h 43m
Delta
Fri 11/137:40 pm
ORD
- MBJ
1 stop17h 55m
Delta
Deal found 6/14![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/55:59 pm
MBJ
- MDW
2 stops19h 34m
Delta
Mon 11/96:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Deal found 6/14![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/134:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Mon 8/175:30 am
ORD
- MBJ
1 stop6h 14m
Delta
Deal found 6/14![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am
KIN
- ORD
2 stops11h 09m
American Airlines
Sat 9/510:00 am
ORD
- KIN
2 stops9h 42m
American Airlines
Deal found 6/17![American Airlines logo]()
$484
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Fri 7/311:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Fri 8/711:06 am
MDW
- MBJ
2 stops22h 06m
Frontier
Deal found 6/16![Frontier logo]()
$485
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/42:32 pm
MBJ
- MDW
1 stop8h 38m
Delta
Mon 11/96:00 am
MDW
- MBJ
1 stop7h 15m
Delta
Deal found 6/14![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:00 pm
MBJ
- MDW
1 stop9h 20m
Southwest
Tue 11/105:15 am
MDW
- MBJ
1 stop8h 30m
Southwest
Deal found 6/14![Southwest logo]()
$502
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/42:32 pm
MBJ
- MDW
1 stop8h 38m
Delta
Sun 11/86:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Deal found 6/14![Delta logo]()
$368
This Copa Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/152:56 pm
KIN
- ORD
1 stop13h 04m
Copa Airlines
Fri 7/241:20 am
ORD
- KIN
1 stop12h 34m
Copa Airlines
Deal found 6/13![Copa Airlines logo]()
$540
This Cheapflightsfares deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
Wed 7/151:55 pm
KIN
- ORD
1 stop9h 49m
JetBlue
Sat 7/252:35 pm
ORD
- KIN
1 stop6h 42m
JetBlue
Deal found 6/13![JetBlue logo]()
$549
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/246:20 am
KIN
- ORD
1 stop13h 33m
American Airlines
Sun 8/25:58 am
ORD
- KIN
2 stops10h 05m
American Airlines
Deal found 6/15![American Airlines logo]()
$530
This Expedia deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
Tue 7/146:28 pm
KIN
- ORD
1 stop19h 11m
JetBlue
Sat 7/257:00 am
ORD
- KIN
1 stop10h 18m
JetBlue
Deal found 6/14![JetBlue logo]()
$549
This Orbitz deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/121:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Sun 7/196:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Deal found 6/15![Frontier logo]()
$551
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 11/236:00 pm
MBJ
- ORD
1 stop6h 50m
Delta
Sun 11/295:30 am
ORD
- MBJ
1 stop10h 05m
Delta
Deal found 6/15![Delta logo]()
$401
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/158:00 am
KIN
- ORD
1 stop14h 01m
American Airlines
Sat 7/255:00 am
ORD
- KIN
2 stops10h 55m
American Airlines
Deal found 6/16![American Airlines logo]()
$540
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/312:20 pm
MBJ
- MDW
2 stops9h 50m
Southwest
Fri 8/77:55 pm
MDW
- MBJ
2 stops15h 25m
Southwest
Deal found 6/16![Southwest logo]()
$607
This Trip.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Tue 8/46:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/18![Frontier logo]()
$585
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/279:00 am
KIN
- ORD
1 stop11h 33m
Delta
Fri 7/316:35 am
ORD
- KIN
1 stop13h 28m
Delta
Deal found 6/16![Delta logo]()
$535
Last-minute flights from Jamaica to ChicagoDiscover last-minute flight deals from Jamaica to Chicago. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Jamaica to Chicago. Data last updated June 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 6/243:00 pm
MBJ
- ORD
1 stop15h 57m
American Airlines
Tue 6/308:19 am
ORD
- MBJ
1 stop7h 57m
American Airlines
Deal found 6/16![American Airlines logo]()
$456
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 6/2412:31 pm
MBJ
- ORD
1 stop11h 27m
American Airlines
Wed 7/19:31 am
ORD
- MBJ
Nonstop4h 00m
American Airlines
Deal found 6/17![American Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/96:20 am
KIN
- ORD
1 stop8h 38m
American Airlines
Thu 8/136:00 am
ORD
- KIN
1 stop13h 42m
American Airlines
Deal found 6/14![American Airlines logo]()
$486
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/103:02 pm
MBJ
- ORD
1 stop8h 28m
American Airlines
Thu 8/135:00 am
ORD
- MBJ
1 stop11h 08m
American Airlines
Deal found 6/14![American Airlines logo]()
$426
This Copa Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
Sun 7/1211:16 am
MBJ
- ORD
1 stop26h 41m
Copa Airlines
Sat 7/181:20 am
ORD
- MBJ
1 stop9h 55m
Copa Airlines
Deal found 6/14![Copa Airlines logo]()
$474
This Copa Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/1412:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Mon 8/243:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Deal found 6/17![Copa Airlines logo]()
$436
This Copa Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/1412:22 pm
MBJ
- ORD
1 stop25h 35m
Copa Airlines
Sat 7/258:02 am
ORD
- MBJ
1 stop27h 13m
Copa Airlines
Deal found 6/15![Copa Airlines logo]()
$447
This Copa Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/1712:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Tue 8/183:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Deal found 6/13![Copa Airlines logo]()
$451
This Orbitz deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Fri 7/171:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Fri 7/2412:11 pm
MDW
- MBJ
1 stop24h 16m
Frontier
Deal found 6/17![Frontier logo]()
$475
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/305:14 pm
MBJ
- ORD
1 stop7h 12m
American Airlines
Thu 8/64:10 pm
ORD
- MBJ
1 stop19h 32m
American Airlines
Deal found 6/15![American Airlines logo]()
$458
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Fri 7/311:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Fri 8/76:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/16![Frontier logo]()
$455
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/314:12 pm
MBJ
- ORD
1 stop26h 38m
United Airlines
Fri 8/75:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Deal found 6/16![United Airlines logo]()
$472
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 June 18, 2026.
Search for one-way flight options from Jamaica to Chicago. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 12/103:36 pm
MBJ
- ORD
1 stop9h 06m
United Airlines
Deal found 6/16![United Airlines logo]()
$199
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 12/123:36 pm
MBJ
- ORD
1 stop9h 06m
United Airlines
Deal found 6/17![United Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 12/116:00 pm
MBJ
- ORD
1 stop6h 50m
Delta
Deal found 6/16![Delta logo]()
$205
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 12/93:40 pm
MBJ
- MDW
1 stop7h 30m
Delta
Deal found 6/14![Delta logo]()
$205
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/1012:52 pm
MBJ
- ORD
1 stop11h 36m
United Airlines
Deal found 6/15![United Airlines logo]()
$208
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:59 pm
MBJ
- MDW
1 stop16h 51m
Delta
Deal found 6/16![Delta logo]()
$208
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 6/252:40 pm
MBJ
- ORD
1 stop17h 19m
United Airlines
Deal found 6/14![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:59 pm
MBJ
- ORD
1 stop8h 38m
Delta
Deal found 6/16![Delta logo]()
$210
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:59 pm
MBJ
- MDW
2 stops16h 08m
Delta
Deal found 6/15![Delta logo]()
$210
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/44:33 pm
MBJ
- ORD
1 stop15h 26m
United Airlines
Deal found 6/17![United Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:59 pm
MBJ
- ORD
2 stops20h 05m
Delta
Deal found 6/16![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 12/116:00 pm
MBJ
- MDW
1 stop16h 52m
Delta
Deal found 6/16![Delta logo]()
$213
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 June 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (United Airlines) |
One-way from | $199 (United Airlines) |
Popular in | March |
Cheapest in | July |
Average price | $568 |
Good round-trip deal | $426 or less |
Good one-way deal | $286 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 June 18, 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
Quickest round-trip
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Mon 11/23
2:48 pm-6:16 pm
Nonstop4h 28m
Chicago O'Hare Intl
Sun 11/29
8:42 am-1:46 pm
Nonstop4h 04m
$311
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 10/16
1:32 pm-8:20 pm
1 stop6h 48m
Chicago O'Hare Intl
Mon 10/19
7:10 am-1:20 pm
1 stop6h 10m
$317
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Wed 11/4
1:50 pm-9:33 pm
1 stop8h 43m
Chicago O'Hare Intl
Fri 11/13
7:40 pm-2:35 pm
1 stop17h 55m
$322
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Thu 11/5
5:59 pm-12:33 pm
2 stops19h 34m
Chicago Midway
Mon 11/9
6:00 am-4:35 pm
1 stop9h 35m
$322
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 8/13
4:59 pm-7:56 am
2 stops14h 57m
Chicago O'Hare Intl
Mon 8/17
5:30 am-11:44 am
1 stop6h 14m
$359
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Wed 11/4
2:32 pm-10:10 pm
1 stop8h 38m
Chicago Midway
Mon 11/9
6:00 am-2:15 pm
1 stop7h 15m
$365
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Wed 11/4
2:32 pm-10:10 pm
1 stop8h 38m
Chicago Midway
Sun 11/8
6:00 am-4:34 pm
1 stop9h 34m
$368
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 8/13
2:12 pm-6:55 pm
Nonstop4h 43m
Chicago O'Hare Intl
Mon 8/17
9:00 am-1:12 pm
Nonstop4h 12m
$399
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Mon 11/23
6:00 pm-11:50 pm
1 stop6h 50m
Chicago O'Hare Intl
Sun 11/29
5:30 am-4:35 pm
1 stop10h 05m
$401
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Tue 7/14
12:22 pm-4:00 am
1 stop15h 38m
Chicago O'Hare Intl
Mon 8/24
3:21 pm-11:15 am
1 stop19h 54m
$436
Showing 1-10 of 51 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
KIN-ORD
MBJ-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Jamaica to Chicago
JM0-CHI
MBJ-ORD
KIN-ORD
MBJ-MDW
What is the cheapest month to book a flight from Jamaica to Chicago?
Currently, April is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $146). Flying from Jamaica to Chicago in January is currently the most expensive (average of $397). 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 June 18, 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.
Weekly flight availability from Jamaica to Chicago
Explore weekly flight availability from Jamaica to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 18, 2026.
The most flights from JM0 to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
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 June 18, 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.
Comfort
7.2
Boarding
7.5
Entertainment
6.8
Overall
7.1
Crew
7.9
Food
6.4
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
Comfort
7.2
Boarding
7.5
Entertainment
6.8
Overall
7.1
Crew
7.9
Food
6.4
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
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
Hammond
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 June 18, 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 June 18, 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$280 | Average$387 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$281 | Average$464 | FlexibilityNo cancel fee | On-time71% |