$210+ Cheap flights from Montego Bay (MBJ) to Chicago (CHI)
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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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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
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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 October 30, 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 October 30, 2026.
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 11/231:50 pm -
1 stop20h 33m
Sun 11/298:40 pm -
1 stop19h 40m
Deal found 10/26![Air Canada logo]()
$377
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:20 pm -
2 stops18h 40m
Sun 11/299:21 pm -
1 stop18h 59m
Deal found 10/25![Air Canada logo]()
$381
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:43 pm -
1 stop8h 30m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/26![Frontier logo]()
$392
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:50 pm -
1 stop28h 53m
Wed 12/28:45 am -
1 stop7h 35m
Deal found 10/26![Air Canada logo]()
$394
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:43 pm -
1 stop17h 31m
Thu 11/267:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$405
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:23 pm -
1 stop21h 28m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$407
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:43 pm -
1 stop8h 04m
Tue 11/249:09 am -
1 stop26h 47m
Deal found 10/29![Frontier logo]()
$420
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:01 pm -
1 stop24h 44m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$430
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:16 pm -
1 stop9h 38m
Sun 11/296:00 am -
1 stop9h 57m
Deal found 10/25![Delta logo]()
$465
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:43 pm -
1 stop20h 12m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$467
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 11/251:50 pm -
1 stop10h 25m
Wed 12/26:00 am -
1 stop7h 25m
Deal found 10/26![Southwest logo]()
$566
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.
Thu 11/191:50 pm -
2 stops8h 45m
Sun 11/228:40 pm -
2 stops16h 45m
Deal found 10/26![Southwest logo]()
$601
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 October 30, 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 October 30, 2026.
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 11/236:20 pm -
2 stops17h 47m
Sun 11/298:40 pm -
1 stop19h 40m
Deal found 10/26![Air Canada logo]()
$380
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:01 pm -
1 stop24h 44m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$430
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.
Thu 4/221:52 pm -
Nonstop4h 23m
Wed 4/286:00 am -
1 stop7h 10m
Deal found 10/25![United Airlines logo]()
$457
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:12 pm -
1 stop6h 42m
Sun 11/295:30 am -
1 stop6h 21m
Deal found 10/25![Delta logo]()
$465
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 11/253:45 pm -
2 stops9h 35m
Wed 12/26:00 am -
1 stop7h 25m
Deal found 10/26![Southwest logo]()
$571
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:20 pm -
2 stops18h 40m
Sun 11/299:21 pm -
1 stop18h 59m
Deal found 10/25![Air Canada logo]()
$381
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:50 pm -
3 stops34h 57m
Wed 11/258:42 pm -
3 stops39h 43m
Deal found 10/29![Multiple Airlines logo]()
$867
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:54 pm -
Nonstop4h 26m
Sun 11/298:40 am -
Nonstop4h 08m
Deal found 10/27![United Airlines logo]()
$462
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:16 pm -
1 stop9h 38m
Sun 11/296:00 am -
1 stop9h 57m
Deal found 10/25![Delta logo]()
$465
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.
Fri 11/201:50 pm -
2 stops10h 20m
Sun 11/228:40 pm -
2 stops16h 45m
Deal found 10/26![Southwest logo]()
$601
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.
Thu 11/123:25 pm -
1 stop8h 50m
Wed 11/255:25 am -
1 stop8h 20m
Deal found 10/29![Southwest logo]()
$624
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:40 pm -
2 stops20h 06m
Wed 11/2512:30 pm -
3 stops24h 05m
Deal found 10/29![WestJet logo]()
$1,508
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.
Fri 12/113:45 pm -
1 stop8h 15m
Fri 12/187:10 am -
1 stop6h 15m
Deal found 10/27![Southwest logo]()
$882
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:35 pm -
2 stops17h 26m
Fri 12/186:01 am -
3 stops27h 55m
Deal found 10/27![Multiple Airlines logo]()
$1,225
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:20 pm -
3 stops23h 31m
Sun 11/226:44 pm -
3 stops21h 36m
Deal found 10/26![Multiple Airlines logo]()
$1,515
Last-minute flights from Montego Bay to ChicagoDiscover last-minute flight deals from Montego Bay to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Montego Bay to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:23 pm -
1 stop21h 28m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$407
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:43 pm -
1 stop8h 04m
Tue 11/249:09 am -
1 stop26h 47m
Deal found 10/29![Frontier logo]()
$420
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:43 pm -
1 stop17h 31m
Thu 11/267:49 am -
1 stop28h 07m
Deal found 10/29![Frontier logo]()
$405
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:43 pm -
1 stop8h 30m
Sun 11/227:49 am -
1 stop28h 07m
Deal found 10/26![Frontier logo]()
$392
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:43 pm -
1 stop20h 12m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$467
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.
Thu 11/191:50 pm -
2 stops8h 45m
Sun 11/228:40 pm -
2 stops16h 45m
Deal found 10/26![Southwest logo]()
$601
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:20 pm -
2 stops18h 40m
Sun 11/299:21 pm -
1 stop18h 59m
Deal found 10/25![Air Canada logo]()
$381
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:01 pm -
1 stop24h 44m
Sun 11/221:16 pm -
1 stop22h 40m
Deal found 10/26![Frontier logo]()
$430
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:16 pm -
1 stop9h 38m
Sun 11/296:00 am -
1 stop9h 57m
Deal found 10/25![Delta 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.
Mon 11/231:50 pm -
1 stop20h 33m
Sun 11/298:40 pm -
1 stop19h 40m
Deal found 10/26![Air Canada logo]()
$377
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:50 pm -
1 stop28h 53m
Wed 12/28:45 am -
1 stop7h 35m
Deal found 10/26![Air Canada logo]()
$394
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 11/251:50 pm -
1 stop10h 25m
Wed 12/26:00 am -
1 stop7h 25m
Deal found 10/26![Southwest logo]()
$566
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 October 30, 2026.
Search for one-way flight options from Montego Bay to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
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.
Sat 2/272:35 pm -
Nonstop4h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$210
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:50 pm -
1 stop20h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Air Canada logo]()
$217
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 12/61:16 pm -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$224
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:22 pm -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$233
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:20 pm -
1 stop21h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Air Canada logo]()
$236
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:01 pm -
1 stop10h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$237
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 12/32:18 pm -
1 stop26h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$238
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:20 pm -
1 stop24h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Air Canada logo]()
$240
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 11/74:43 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$241
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.
Sun 12/62:22 pm -
1 stop26h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$249
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:01 pm -
1 stop19h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$253
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.
Tue 12/222:59 pm -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$254
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $377 (Air Canada) |
One-way from | $210 (American Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $469 |
Good round-trip deal | $461 or less |
Good one-way deal | $294 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 7,457,451 searches. Data last updated October 30, 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
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Mon 11/9
6:20 pm-8:00 am
2 stops14h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$270
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Fri 12/25
8:00 am-5:44 pm
2 stops10h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Wed 12/23
8:00 am-4:19 pm
1 stop9h 19m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Thu 1/21
6:09 pm-11:55 pm
1 stop6h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$280
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Wed 2/3
6:09 pm-10:04 am
1 stop16h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$284
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Fri 2/5
12:39 pm-11:55 pm
1 stop12h 16m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$284
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Mon 2/1
6:09 pm-8:40 am
1 stop15h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$290
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Mon 2/1
6:09 pm-11:55 pm
1 stop6h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$290
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Sat 1/30
3:35 pm-2:00 pm
2 stops23h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$293
Montego BayChicago
MBJ Montego Bay Sangster Intl - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Sat 1/30
6:09 pm-1:01 pm
2 stops19h 52m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$293
Showing 1-10 of 36 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 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 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, December is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $367). Flying from Montego Bay to Chicago in August is currently the most expensive (average of $643). 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 Montego Bay to Chicago?
Airfare is below average for this route at the moment.
Montego Bay to Chicago flights typically cost between $438 and $701 in November.The cheapest round-trip price found within the last 5 days was $377 on Air Canada (Nov 23-Nov 29).
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 October 30, 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.
Overall
7.0
Boarding
7.4
Comfort
7.1
Crew
7.9
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Overall
7.0
Boarding
7.4
Comfort
7.1
Crew
7.9
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Complete your trip
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Montego Bay and Chicago flights
Browse other Montego Bay and Chicago flight options. Last updated on October 30, 2026.
Other flights from Montego Bay
Browse through other flights departing from Montego Bay. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$281 | Average$431 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$281 | Average$418 | FlexibilityNo cancel fee | On-time71% |