$183+ Cheap flights from Montego Bay (MBJ) 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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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 Montego Bay to ChicagoExplore the most affordable flight options available from Montego Bay to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2026.
Explore the most affordable flight options available from Montego Bay to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 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 6/14. 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.
Tue 11/31:50 pm
MBJ
- ORD
1 stop8h 43m
Delta
Tue 11/107:10 am
ORD
- MBJ
1 stop6h 05m
Delta
Deal found 6/14![Delta logo]()
$317
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 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
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.
Tue 11/31:50 pm
MBJ
- ORD
1 stop8h 43m
Delta
Fri 11/135:55 pm
ORD
- MBJ
2 stops17h 30m
Delta
Deal found 6/14![Delta logo]()
$365
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 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 United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/44:12 pm
MBJ
- ORD
1 stop7h 19m
United Airlines
Fri 8/76:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 6/11![United Airlines logo]()
$369
Best flights from Montego Bay to ChicagoDiscover carefully curated flight deals from Montego Bay to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
Discover carefully curated flight deals from Montego Bay to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 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 6/14. 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 Priceline deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Tue 8/41:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Fri 8/76:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/11![Frontier logo]()
$435
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 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 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.
Wed 11/42:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Tue 11/105:00 am
ORD
- MBJ
1 stop8h 29m
United Airlines
Deal found 6/14![United Airlines logo]()
$316
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 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 United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/44:12 pm
MBJ
- ORD
1 stop7h 19m
United Airlines
Fri 8/76:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 6/11![United Airlines logo]()
$369
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.
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 Copa Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/812:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Sat 7/111:20 am
ORD
- MBJ
1 stop8h 51m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$451
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.
Mon 11/236:00 pm
MBJ
- ORD
1 stop6h 50m
Delta
Sun 11/295:30 am
ORD
- MBJ
1 stop10h 05m
Delta
Deal found 6/14![Delta logo]()
$401
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 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 11/193:36 pm
MBJ
- ORD
1 stop9h 06m
United Airlines
Sun 11/297:10 am
ORD
- MBJ
1 stop30h 19m
United Airlines
Deal found 6/15![United Airlines logo]()
$473
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2811:45 am
MBJ
- MDW
2 stops8h 05m
Southwest
Tue 8/46:15 am
MDW
- MBJ
1 stop6h 55m
Southwest
Deal found 6/13![Southwest logo]()
$579
This Frontier deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Tue 7/141:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Mon 8/246:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Deal found 6/11![Frontier logo]()
$551
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/1411:45 am
MBJ
- MDW
2 stops8h 05m
Southwest
Mon 8/247:50 pm
MDW
- MBJ
2 stops17h 05m
Southwest
Deal found 6/11![Southwest logo]()
$581
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/110:27 am
MBJ
- MDW
2 stops48h 40m
Frontier
Sat 8/2211:59 am
MDW
- MBJ
1 stop24h 22m
Frontier
Deal found 6/11![Frontier logo]()
$584
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1711:45 am
MBJ
- MDW
2 stops10h 15m
Southwest
Tue 8/186:15 am
MDW
- MBJ
1 stop5h 40m
Southwest
Deal found 6/13![Southwest logo]()
$584
Last-minute flights from Montego Bay to ChicagoDiscover last-minute flight deals from Montego Bay to Chicago. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Montego Bay to Chicago. Data last updated June 16, 2026 and is based on user searches.
This American 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 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 6/13![American Airlines logo]()
$456
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:12 pm
MBJ
- ORD
1 stop16h 16m
United Airlines
Tue 7/76:00 am
ORD
- MBJ
1 stop9h 10m
United Airlines
Deal found 6/13![United Airlines logo]()
$496
This Priceline deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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.
Wed 7/81:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Sun 7/126:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Deal found 6/12![Frontier logo]()
$435
This Copa Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/812:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Sat 7/111:20 am
ORD
- MBJ
1 stop8h 51m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$451
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/93:02 pm
MBJ
- ORD
1 stop9h 27m
American Airlines
Sun 8/167:09 am
ORD
- MBJ
1 stop6h 40m
American Airlines
Deal found 6/12![American Airlines logo]()
$449
This Trip.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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.
Thu 7/91:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Tue 8/116:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/12![Frontier logo]()
$496
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 6/15. 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 American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/142:36 pm
MBJ
- ORD
Nonstop4h 51m
American Airlines
Mon 8/249:00 am
ORD
- MBJ
Nonstop4h 12m
American Airlines
Deal found 6/11![American Airlines logo]()
$481
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Tue 8/46:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/13![Frontier logo]()
$506
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
One-way flights from Montego Bay to ChicagoSearch for one-way flight options from Montego Bay to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
Search for one-way flight options from Montego Bay to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 6/11![United Airlines logo]()
$183
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/52:40 pm
MBJ
- ORD
1 stop18h 25m
United Airlines
Deal found 6/11![United Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 12/85:04 pm
MBJ
- ORD
1 stop17h 04m
American Airlines
Deal found 6/11![American Airlines logo]()
$193
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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
- ORD
1 stop9h 10m
Delta
Deal found 6/11![Delta logo]()
$200
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 6/11![Delta logo]()
$200
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/64:59 pm
MBJ
- ORD
2 stops20h 09m
Delta
Deal found 6/11![Delta logo]()
$203
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 12/86:00 pm
MBJ
- MDW
1 stop16h 52m
Delta
Deal found 6/11![Delta logo]()
$203
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 12/113:40 pm
MBJ
- ORD
1 stop9h 10m
Delta
Deal found 6/12![Delta logo]()
$205
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 stop20h 52m
United Airlines
Deal found 6/12![United Airlines logo]()
$208
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 6/12![Delta logo]()
$208
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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
Deal found 6/12![American Airlines logo]()
$209
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:55 pm
MBJ
- ORD
1 stop10h 49m
JetBlue
Deal found 6/14![JetBlue logo]()
$210
Find flight deals from Montego Bay to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Montego Bay (MBJ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (United Airlines) |
One-way from | $183 (United Airlines) |
Popular in | March |
Cheapest in | July |
Average price | $500 |
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 Montego Bay 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 16, 2026.
Use the filters below to find and compare flights from Montego Bay 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
Wed 11/4
2:48 pm-6:16 pm
Nonstop4h 28m
Chicago O'Hare Intl
Tue 11/10
5:00 am-2:29 pm
1 stop8h 29m
$316
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
Tue 8/4
4:12 pm-11:31 pm
1 stop7h 19m
Chicago O'Hare Intl
Fri 8/7
6:30 am-3:10 pm
1 stop8h 40m
$369
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 - MDW
MBJMDW
Montego Bay Sangster Intl
Tue 8/4
1:32 pm-10:03 pm
1 stop8h 31m
Chicago Midway
Fri 8/7
6:05 am-12:27 pm
1 stop6h 22m
$435
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Tue 7/14
12:22 pm-1:57 pm
1 stop25h 35m
Chicago O'Hare Intl
Sat 7/25
8:02 am-11:15 am
1 stop27h 13m
$447
Showing 1-10 of 35 resultsSorted by cheapest first
Compare providers for flights from Montego Bay to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Montego Bay to Chicago in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Montego Bay-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montego Bay-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Montego Bay-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Montego Bay-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Montego Bay-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Montego Bay to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Montego Bay with our price prediction graph.
MBJ-CHI
MBJ-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 Montego Bay to Chicago
MBJ-CHI
MBJ-ORD
MBJ-MDW
What is the cheapest month to book a flight from Montego Bay to Chicago?
Currently, April is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $146). Flying from Montego Bay 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 MBJ to CHI?
Find hourly flight availability from Montego Bay 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 16, 2026.
When flying from Montego Bay to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Montego Bay to Chicago
Explore weekly flight availability from Montego Bay 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 16, 2026.
The most flights from MBJ 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).
How much does it cost to fly round-trip from Montego Bay to Chicago?
The best insider tips for Montego Bay to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Montego Bay to Chicago trip
Our travel experts
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 16, 2026.
See what other customers who have flown with American Airlines from Montego Bay to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Food
6.4
Overall
7.1
Crew
7.9
Boarding
7.5
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
Entertainment
6.8
Food
6.4
Overall
7.1
Crew
7.9
Boarding
7.5
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
Related info for your journey
Find useful and relevant information for your journey from Montego Bay 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
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Other flights to Chicago
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Montego Bay and Chicago flights
Browse other Montego Bay and Chicago flight options. Last updated on June 16, 2026.
Other flights from Montego Bay
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Top 2 airlines flying from Montego Bay to Chicago
Discover the top 2 airlines that operate flights from Montego Bay 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 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$280 | Average$387 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$281 | Average$409 | FlexibilityNo cancel fee | On-time71% |