$184+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Nov 29 — Dec 61
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 59 days in advance, depart on a Tuesday or Monday and return on a Tuesday
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 October 30, 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 October 30, 2026.
This Air Canada deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/145:58 pm -
2 stops18h 27m
Tue 11/241:50 pm -
1 stop20h 33m
Deal found 10/27![Air Canada logo]()
$465
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 10/313:45 pm -
2 stops21h 05m
Tue 11/31:50 pm -
1 stop20h 33m
Deal found 10/26![Air Canada logo]()
$468
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:08 am -
1 stop8h 00m
Mon 11/232:01 pm -
1 stop19h 13m
Deal found 10/28![Frontier logo]()
$469
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 stop27h 54m
Deal found 10/27![Multiple Airlines logo]()
$469
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/145:58 pm -
2 stops18h 27m
Thu 11/191:50 pm -
2 stops19h 10m
Deal found 10/26![Air Canada logo]()
$470
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:30 pm -
1 stop18h 46m
Wed 12/911:05 am -
1 stop8h 20m
Deal found 10/28![American Airlines logo]()
$471
This Justfly.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
1 stop23h 49m
Thu 12/102:22 pm -
1 stop26h 44m
Deal found 10/30![Frontier logo]()
$472
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:58 pm -
2 stops42h 27m
Sun 12/62:22 pm -
1 stop8h 20m
Deal found 10/28![Multiple Airlines logo]()
$472
This Justfly.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Thu 11/197:50 pm -
1 stop16h 06m
Mon 11/236:20 pm -
1 stop16h 24m
Deal found 10/27![Multiple Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/69:40 am -
Nonstop4h 13m
Wed 12/93:58 pm -
Nonstop4h 47m
Deal found 10/28![American Airlines logo]()
$476
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:42 pm -
1 stop19h 26m
Mon 11/232:01 pm -
1 stop23h 20m
Deal found 10/27![Frontier logo]()
$477
This Orbitz deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:45 am -
2 stops27h 40m
Mon 11/236:20 pm -
2 stops25h 10m
Deal found 10/27![Air Canada logo]()
$478
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 October 30, 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 October 30, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/227:35 am -
1 stop26h 40m
Mon 3/112:20 pm -
1 stop25h 26m
Deal found 10/25![Copa Airlines logo]()
$500
This JetBlue deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/167:00 am -
1 stop6h 05m
Tue 2/233:00 pm -
1 stop9h 37m
Deal found 10/29![JetBlue logo]()
$509
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:00 am -
2 stops8h 44m
Wed 2/36:09 pm -
2 stops19h 55m
Deal found 10/28![Delta logo]()
$516
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:25 am -
1 stop8h 20m
Wed 12/21:50 pm -
1 stop6h 45m
Deal found 10/28![Southwest logo]()
$525
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/228:40 am -
Nonstop4h 08m
Mon 3/11:25 pm -
1 stop9h 28m
Deal found 10/25![United Airlines logo]()
$547
This JetBlue deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 1/177:50 pm -
1 stop12h 48m
Sat 1/232:41 pm -
1 stop10h 06m
Deal found 10/25![JetBlue logo]()
$515
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 4/97:35 pm -
1 stop15h 55m
Tue 4/132:25 pm -
2 stops17h 14m
Deal found 10/26![Delta logo]()
$522
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 2/226:30 am -
1 stop6h 40m
Mon 3/14:00 pm -
1 stop8h 00m
Deal found 10/25![Southwest logo]()
$552
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/178:39 am -
Nonstop4h 09m
Mon 3/221:54 pm -
Nonstop4h 26m
Deal found 10/28![United Airlines logo]()
$558
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:40 am -
Nonstop4h 08m
Sun 12/133:45 pm -
1 stop8h 10m
Deal found 10/28![United Airlines logo]()
$572
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/176:35 am -
1 stop6h 35m
Wed 2/241:10 pm -
1 stop8h 35m
Deal found 10/26![Southwest logo]()
$589
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
1 stop9h 57m
Wed 12/92:19 pm -
1 stop9h 35m
Deal found 10/29![Delta logo]()
$599
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/238:40 am -
Nonstop4h 08m
Wed 1/272:54 pm -
Nonstop4h 26m
Deal found 10/28![United Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 3/297:35 pm -
1 stop15h 55m
Sun 4/42:25 pm -
1 stop19h 08m
Deal found 10/27![Delta logo]()
$600
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop7h 25m
Sat 12/51:25 pm -
1 stop8h 00m
Deal found 10/29![Southwest logo]()
$645
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/48:40 am -
Nonstop4h 08m
Mon 1/112:54 pm -
Nonstop4h 26m
Deal found 10/28![United Airlines logo]()
$604
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/46:00 am -
1 stop9h 44m
Mon 2/86:09 pm -
1 stop6h 46m
Deal found 10/26![Delta logo]()
$606
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/176:35 am -
1 stop6h 35m
Sat 1/2312:45 pm -
2 stops11h 00m
Deal found 10/29![Southwest logo]()
$658
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:40 am -
Nonstop4h 08m
Sun 12/62:54 pm -
Nonstop4h 26m
Deal found 10/29![United Airlines logo]()
$612
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/205:25 am -
1 stop6h 35m
Sun 1/242:00 pm -
1 stop8h 00m
Deal found 10/25![Southwest logo]()
$698
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 3/66:00 am -
1 stop8h 25m
Wed 3/102:35 pm -
1 stop8h 35m
Deal found 10/26![Delta logo]()
$752
Last-minute flights from Chicago to Montego BayDiscover last-minute flight deals from Chicago to Montego Bay. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Montego Bay. Data last updated October 30, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 10/313:45 pm -
2 stops21h 05m
Tue 11/31:50 pm -
1 stop20h 33m
Deal found 10/26![Air Canada logo]()
$468
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 stop27h 54m
Deal found 10/27![Multiple Airlines logo]()
$469
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:42 pm -
1 stop19h 26m
Mon 11/232:01 pm -
1 stop23h 20m
Deal found 10/27![Frontier logo]()
$477
This Orbitz deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:45 am -
2 stops27h 40m
Mon 11/236:20 pm -
2 stops25h 10m
Deal found 10/27![Air Canada logo]()
$478
This Air Canada deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/145:58 pm -
2 stops18h 27m
Tue 11/241:50 pm -
1 stop20h 33m
Deal found 10/27![Air Canada logo]()
$465
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/145:58 pm -
2 stops18h 27m
Thu 11/191:50 pm -
2 stops19h 10m
Deal found 10/26![Air Canada logo]()
$470
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:08 am -
1 stop8h 00m
Mon 11/232:01 pm -
1 stop19h 13m
Deal found 10/28![Frontier logo]()
$469
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:42 pm -
1 stop17h 14m
Sun 11/222:01 pm -
1 stop19h 13m
Deal found 10/28![Frontier logo]()
$472
This Justfly.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Thu 11/197:50 pm -
1 stop16h 06m
Mon 11/236:20 pm -
1 stop16h 24m
Deal found 10/27![Multiple Airlines logo]()
$474
This CheapOair deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:49 am -
1 stop28h 07m
Wed 11/251:50 pm -
2 stops19h 10m
Deal found 10/28![Multiple Airlines logo]()
$476
This Travelocity deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Mon 11/237:49 am -
1 stop28h 07m
Wed 12/26:20 pm -
1 stop26h 38m
Deal found 10/25![Multiple Airlines logo]()
$482
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:41 am -
1 stop6h 51m
Wed 12/211:05 am -
1 stop8h 20m
Deal found 10/28![American Airlines logo]()
$471
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 October 30, 2026.
Search for one-way flight options from Chicago to Montego Bay. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Super.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:08 am -
1 stop8h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Sat 11/147:05 am -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$184
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/147:15 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$189
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:45 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Air Canada logo]()
$196
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:49 am -
1 stop28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$202
This Trip.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/278:40 pm -
1 stop19h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Air Canada logo]()
$213
This Frontier deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/285:58 am -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$222
This Orbitz deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:30 pm -
2 stops19h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Air Canada logo]()
$224
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/169:40 am -
Nonstop4h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/235:05 am -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:25 am -
1 stop13h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$231
This FlightHub deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:40 pm -
1 stop21h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$233
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $465 (Air Canada) |
One-way from | $184 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $522 |
Good round-trip deal | $626 or less |
Good one-way deal | $268 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 October 30, 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
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/29
6:00 am-9:10 pm
1 stop14h 10m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$231
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 11/23
5:05 am-2:25 pm
1 stop8h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$231
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 11/15
7:00 am-2:57 pm
1 stop6h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sat 11/21
7:49 am-12:56 pm
1 stop28h 07m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
Quickest round-trip
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Fri 1/22
7:00 am-2:12 pm
1 stop6h 12m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/29
1:11 pm-1:44 pm
1 stop23h 33m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$253
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 3/22
6:00 am-1:39 pm
1 stop7h 39m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$257
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Wed 11/18
5:55 am-2:14 pm
1 stop7h 19m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$258
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 11/15
5:05 am-2:45 pm
2 stops8h 40m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$277
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/29
6:52 am-12:45 pm
2 stops28h 53m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
Showing 1-10 of 39 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
MDW-MBJ
ORD-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
MDW-MBJ
ORD-MBJ
What is the cheapest month to book a flight from Chicago to Montego Bay?
Currently, April is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $472). Flying from Chicago to Montego Bay in December is currently the most expensive (average of $694). 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 $449 and $697 in November.The cheapest round-trip price found within the last 5 days was $465 on Air Canada (Nov 14-Nov 24).
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 58 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 October 30, 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.
Overall
7.9
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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
Explore flights to Montego Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$584 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$552 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$301 | Average$575 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$550 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$322 | Average$625 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |