$163+ Cheap flights from Chicago (CHI) to Montego Bay (MBJ)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Montego Bay 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.Cheapflights Tip: The best prices from Chicago to Montego Bay Sangster Intl are usually found in September or April, booked 89 days in advance, depart on a Tuesday or Sunday and return on a Wednesday
Cheap flight deals from Chicago to Montego Bay
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Cheapest flights from Chicago to Montego BayExplore the most affordable flight options available from Chicago to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
Explore the most affordable flight options available from Chicago to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/178:55 pm -
1 stop14h 13m
Fri 10/2312:18 pm -
1 stop9h 12m
Deal found 9/10![American Airlines logo]()
$430
This FlightHub deal was found by Cheapflights users on 9/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:15 am -
1 stop7h 13m
Tue 11/31:50 pm -
1 stop24h 23m
Deal found 9/13![Multiple Airlines logo]()
$431
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop7h 13m
Mon 11/236:20 pm -
2 stops14h 40m
Deal found 9/14![Multiple Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/109:29 pm -
1 stop18h 43m
Wed 10/145:13 pm -
1 stop16h 17m
Deal found 9/10![American Airlines logo]()
$438
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Sun 11/87:00 am -
1 stop6h 57m
Sat 11/213:00 pm -
1 stop9h 38m
Deal found 9/14![JetBlue logo]()
$439
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:29 pm -
1 stop16h 46m
Tue 11/33:56 pm -
Nonstop4h 50m
Deal found 9/10![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 11/309:37 am -
Nonstop4h 12m
Wed 2/173:46 pm -
1 stop16h 39m
Deal found 9/14![American Airlines logo]()
$441
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:46 pm -
1 stop17h 16m
Fri 10/303:23 pm -
1 stop8h 24m
Deal found 9/14![Frontier logo]()
$441
This Travelocity deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Thu 10/227:44 pm -
1 stop18h 49m
Sun 10/251:20 pm -
2 stops20h 03m
Deal found 9/10![Multiple Airlines logo]()
$442
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop8h 18m
Mon 10/263:48 pm -
1 stop7h 55m
Deal found 9/14![Frontier logo]()
$442
This Priceline deal was found by Cheapflights users on 9/11. 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.
Sat 10/246:21 pm -
2 stops18h 04m
Sat 10/313:50 pm -
1 stop18h 06m
Deal found 9/11![Multiple Airlines logo]()
$443
This Expedia deal was found by Cheapflights users on 9/14. 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.
Fri 11/67:50 pm -
1 stop18h 38m
Mon 11/96:20 pm -
1 stop26h 38m
Deal found 9/14![Multiple Airlines logo]()
$444
Best flights from Chicago to Montego BayDiscover carefully curated flight deals from Chicago to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
Discover carefully curated flight deals from Chicago to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:30 am -
1 stop8h 09m
Wed 3/33:20 pm -
1 stop8h 38m
Deal found 9/9![United Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 11/146:49 am -
1 stop9h 08m
Tue 11/246:12 pm -
1 stop6h 42m
Deal found 9/11![Delta logo]()
$462
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:00 am -
1 stop6h 57m
Tue 11/243:00 pm -
1 stop9h 38m
Deal found 9/12![JetBlue logo]()
$472
This Southwest deal was found by Cheapflights users on 9/14. 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 9/296:30 am -
1 stop6h 25m
Fri 10/3012:00 pm -
2 stops11h 10m
Deal found 9/14![Southwest logo]()
$487
This United Airlines deal was found by Cheapflights users on 9/11. 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 11/125:55 am -
1 stop7h 19m
Tue 11/172:54 pm -
Nonstop4h 26m
Deal found 9/11![United Airlines logo]()
$472
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Sun 10/187:00 am -
1 stop7h 05m
Mon 10/1912:01 pm -
1 stop11h 29m
Deal found 9/14![JetBlue logo]()
$477
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 pm -
1 stop17h 30m
Sat 11/211:55 pm -
1 stop8h 47m
Deal found 9/13![Delta logo]()
$482
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:55 pm -
2 stops14h 55m
Thu 10/2212:50 pm -
1 stop9h 10m
Deal found 9/10![Southwest logo]()
$490
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/288:40 am -
Nonstop4h 08m
Sun 11/12:54 pm -
Nonstop4h 26m
Deal found 9/14![United Airlines logo]()
$480
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop6h 57m
Wed 11/253:00 pm -
1 stop9h 38m
Deal found 9/13![JetBlue logo]()
$481
This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 11/146:00 am -
1 stop9h 57m
Sat 11/212:16 pm -
1 stop9h 38m
Deal found 9/14![Delta logo]()
$482
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sun 11/155:05 am -
2 stops8h 40m
Fri 11/201:50 pm -
2 stops10h 20m
Deal found 9/14![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/35:27 am -
1 stop6h 24m
Tue 11/106:12 pm -
2 stops14h 34m
Deal found 9/10![Delta logo]()
$490
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sun 10/259:20 pm -
2 stops14h 30m
Wed 10/2812:00 pm -
2 stops10h 15m
Deal found 9/13![Southwest logo]()
$561
This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 1/236:00 am -
1 stop7h 10m
Sat 1/303:40 pm -
1 stop7h 30m
Deal found 9/14![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 11/148:40 am -
Nonstop4h 08m
Mon 11/232:54 pm -
Nonstop4h 26m
Deal found 9/11![United Airlines logo]()
$588
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sat 9/265:55 am -
1 stop6h 30m
Sat 10/312:55 pm -
1 stop9h 20m
Deal found 9/14![Southwest logo]()
$599
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 12/55:00 am -
1 stop6h 50m
Sat 12/121:25 pm -
2 stops9h 55m
Deal found 9/13![Southwest logo]()
$606
This Delta deal was found by Cheapflights users on 9/12. 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.
Tue 11/36:04 am -
1 stop5h 47m
Tue 11/102:16 pm -
1 stop9h 38m
Deal found 9/12![Delta logo]()
$613
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 1/97:55 am -
Nonstop3h 55m
Sat 1/161:25 pm -
Nonstop4h 05m
Deal found 9/13![Southwest logo]()
$611
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/296:30 pm -
2 stops16h 30m
Thu 11/53:45 pm -
1 stop8h 15m
Deal found 9/14![Southwest logo]()
$615
Last-minute flights from Chicago to Montego BayDiscover last-minute flight deals from Chicago to Montego Bay. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Montego Bay. Data last updated September 15, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:46 pm -
1 stop17h 16m
Fri 10/303:23 pm -
1 stop8h 24m
Deal found 9/14![Frontier logo]()
$441
This JetBlue deal was found by Cheapflights users on 9/14. 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 10/56:00 am -
1 stop6h 03m
Sat 10/1012:03 pm -
1 stop11h 27m
Deal found 9/14![JetBlue logo]()
$445
This Justfly.com deal was found by Cheapflights users on 9/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 am -
1 stop7h 37m
Sat 10/103:48 pm -
1 stop7h 55m
Deal found 9/14![Frontier logo]()
$445
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/109:29 pm -
1 stop18h 43m
Wed 10/145:13 pm -
1 stop16h 17m
Deal found 9/10![American Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/178:55 pm -
1 stop14h 13m
Fri 10/2312:18 pm -
1 stop9h 12m
Deal found 9/10![American Airlines logo]()
$430
This Travelocity deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Thu 10/227:44 pm -
1 stop18h 49m
Sun 10/251:20 pm -
2 stops20h 03m
Deal found 9/10![Multiple Airlines logo]()
$442
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop8h 18m
Mon 10/263:48 pm -
1 stop7h 55m
Deal found 9/14![Frontier logo]()
$442
This Travelocity deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Fri 10/232:00 pm -
2 stops46h 25m
Mon 10/263:48 pm -
1 stop21h 03m
Deal found 9/10![Multiple Airlines logo]()
$446
This Priceline deal was found by Cheapflights users on 9/11. 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.
Sat 10/246:21 pm -
2 stops18h 04m
Sat 10/313:50 pm -
1 stop18h 06m
Deal found 9/11![Multiple Airlines logo]()
$443
This Priceline deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/307:50 pm -
1 stop18h 38m
Tue 11/31:50 pm -
2 stops22h 17m
Deal found 9/10![Multiple Airlines logo]()
$447
This FlightHub deal was found by Cheapflights users on 9/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:15 am -
1 stop7h 13m
Tue 11/31:50 pm -
1 stop24h 23m
Deal found 9/13![Multiple Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:55 pm -
2 stops13h 20m
Tue 11/36:09 pm -
1 stop7h 35m
Deal found 9/9![American Airlines logo]()
$435
One-way flights from Chicago to Montego BaySearch for one-way flight options from Chicago to Montego Bay. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
Search for one-way flight options from Chicago to Montego Bay. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/135:00 am -
1 stop8h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$163
This Super.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$175
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Sat 10/107:00 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$176
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Sun 9/276:25 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$177
This FlightHub deal was found by Cheapflights users on 9/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:28 pm -
1 stop16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$179
This Trip.com deal was found by Cheapflights users on 9/12. 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.
Sun 10/116:24 am -
1 stop8h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$179
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/121:55 pm -
2 stops23h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Air Canada logo]()
$181
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:28 pm -
1 stop16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$182
This CheapOair deal was found by Cheapflights users on 9/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$182
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:58 pm -
2 stops42h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Air Canada logo]()
$184
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/119:21 pm -
1 stop14h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$189
Find flight deals from Chicago to Montego Bay
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Montego Bay (MBJ). 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 September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $430 (American Airlines) |
One-way from | $163 (American Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $460 |
Good round-trip deal | $482 or less |
Good one-way deal | $202 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Montego Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 15, 2026.
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sat 1/2
5:30 am-8:41 pm
1 stop14h 11m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 9/28
5:55 am-1:15 pm
2 stops7h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 3/8
1:35 pm-11:05 am
2 stops20h 30m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Tue 1/12
6:00 am-2:45 pm
1 stop7h 45m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 1/12
6:00 am-3:25 pm
1 stop8h 25m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/8
6:00 am-4:57 pm
1 stop9h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 12/6
6:00 am-4:57 pm
1 stop9h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 10/6
6:04 am-1:00 pm
1 stop6h 56m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
Quickest round-trip
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Fri 11/6
8:40 am-1:48 pm
Nonstop4h 08m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 11/8
7:30 pm-4:57 pm
2 stops20h 27m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from Chicago to Montego Bay
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 Chicago to Montego Bay in September.
| 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 Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Montego Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Montego Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Montego Bay flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Montego Bay 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 Chicago-Montego Bay 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 Chicago to Montego Bay
Have a flexible travel schedule? Discover the best time to fly to Montego Bay from Chicago with our price prediction graph.
CHI-MBJ
ORD-MBJ
MDW-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Montego Bay
CHI-MBJ
ORD-MBJ
MDW-MBJ
What is the cheapest month to book a flight from Chicago to Montego Bay?
Currently, October is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $467). Flying from Chicago to Montego Bay in December is currently the most expensive (average of $640). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago to Montego Bay?
Airfare is typical for this route at the moment.
Chicago to Montego Bay flights typically cost between $414 and $553 in October.The cheapest round-trip price found within the last 5 days was $430 on American Airlines (Oct 17-Oct 23).
What’s the top layover airport for flights from Chicago to Montego Bay?
Share of 1-stop round-trip flights from Chicago to Montego Bay chosen by Cheapflights users in the past 12 months, using the same layover each way.
Charlotte (CLT) – chosen by Cheapflights users on 40% of 1-stop itineraries from Chicago to Montego Bay on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Montego Bay?
Average round-trip fare for 1-stop flights from Chicago to Montego Bay, chosen by Cheapflights users in the past 12 months, with the same layover each way.
New York (JFK) is the most affordable 1-stop option, with an average round-trip price of $549.
What’s the fastest layover option from Chicago to Montego Bay?
Shortest average travel time for 1-stop one-way flights from Chicago to Montego Bay, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Miami (MIA) have the shortest average one-way travel time for 1-stop routes: 5h 40m.
Which airport typically offers the quickest layover for flights from Chicago to Montego Bay?
Average layover duration for 1-stop one-way flights from Chicago to Montego Bay, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Charlotte (CLT) offer the fastest connection on this route, with an average layover time of 1h 20m.
How far ahead should I book a flight from Chicago to Montego Bay?
The best time to book flights from Chicago to Montego Bay is 13 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
The best insider tips for Chicago to Montego Bay 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 Chicago to Montego Bay trip
Our travel experts
Reviews of airlines servicing Montego Bay
Get insights into the airlines that provide service to Montego Bay. 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 Montego Bay. Reviews last updated September 15, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Chicago to Montego Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Montego Bay. 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 Montego Bay?
Book flights to Montego Bay if you plan to visit one of these locationsLucea
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Other flights to Montego Bay
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Chicago and Montego Bay flights
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Top 6 airlines flying from Chicago to Montego Bay
Discover the top 6 airlines that operate flights from Chicago to Montego Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$462 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$570 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$297 | Average$510 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$302 | Average$547 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$317 | Average$541 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |