$204+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Oct 13 — Oct 201
Round-trip
1 adult, Economy
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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 September 13, 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 September 13, 2026.
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:50 pm -
1 stop26h 48m
Mon 11/164:30 pm -
1 stop19h 20m
Deal found 9/9![Air Canada logo]()
$353
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.
Wed 10/2112:18 pm -
1 stop9h 12m
Sat 10/246:59 pm -
1 stop16h 19m
Deal found 9/10![American Airlines logo]()
$366
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:20 pm -
1 stop16h 03m
Sun 11/294:30 pm -
1 stop23h 50m
Deal found 9/12![Air Canada logo]()
$373
This Air Canada deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 -
1 stop21h 47m
Sat 12/123:45 pm -
1 stop20h 40m
Deal found 9/8![Air Canada logo]()
$380
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/2312:30 pm -
1 stop20h 30m
Fri 10/308:40 pm -
1 stop19h 40m
Deal found 9/8![Air Canada logo]()
$385
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.
Wed 11/113:56 pm -
Nonstop4h 50m
Mon 11/169:40 am -
Nonstop4h 12m
Deal found 9/9![American Airlines logo]()
$391
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:43 pm -
1 stop8h 04m
Sat 11/147:25 am -
1 stop7h 03m
Deal found 9/12![Frontier logo]()
$405
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop11h 05m
Sat 12/125:00 am -
1 stop8h 30m
Deal found 9/8![Southwest logo]()
$504
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:45 pm -
2 stops9h 20m
Sat 11/145:00 am -
1 stop6h 50m
Deal found 9/12![Southwest logo]()
$593
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:00 pm -
2 stops10h 15m
Thu 11/128:40 pm -
2 stops16h 45m
Deal found 9/9![Southwest logo]()
$618
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.
Thu 10/13:42 pm -
1 stop8h 02m
Thu 10/86:40 pm -
1 stop19h 53m
Deal found 9/13![Frontier logo]()
$630
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:42 pm -
1 stop26h 09m
Thu 10/811:45 am -
2 stops27h 50m
Deal found 9/13![Multiple Airlines logo]()
$781
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 September 13, 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 September 13, 2026.
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:50 pm -
1 stop26h 48m
Mon 11/164:30 pm -
1 stop19h 20m
Deal found 9/9![Air Canada logo]()
$353
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:12 pm -
2 stops14h 34m
Tue 11/177:05 am -
2 stops8h 52m
Deal found 9/9![Delta logo]()
$397
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:43 pm -
1 stop8h 04m
Sat 11/147:25 am -
1 stop7h 03m
Deal found 9/12![Frontier logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/8![United Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop11h 05m
Sat 12/125:00 am -
1 stop8h 30m
Deal found 9/8![Southwest logo]()
$504
This Air Canada deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 -
1 stop21h 47m
Sat 12/123:45 pm -
1 stop20h 40m
Deal found 9/8![Air Canada logo]()
$380
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:42 pm -
1 stop26h 09m
Thu 10/811:45 am -
2 stops27h 50m
Deal found 9/13![Multiple Airlines logo]()
$781
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:12 pm -
2 stops14h 34m
Mon 11/167:05 am -
2 stops8h 52m
Deal found 9/9![Delta logo]()
$397
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:20 pm -
1 stop16h 03m
Sun 11/294:30 pm -
1 stop23h 50m
Deal found 9/9![Air Canada logo]()
$390
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/12:20 pm -
1 stop21h 47m
Sat 11/143:45 pm -
1 stop20h 40m
Deal found 9/12![Air Canada logo]()
$407
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:30 pm -
2 stops19h 14m
Sat 10/246:21 pm -
2 stops18h 04m
Deal found 9/10![Air Canada logo]()
$409
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:45 pm -
2 stops9h 20m
Sat 11/145:00 am -
1 stop6h 50m
Deal found 9/12![Southwest logo]()
$593
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.
Thu 10/13:42 pm -
1 stop8h 02m
Thu 10/86:40 pm -
1 stop19h 53m
Deal found 9/13![Frontier logo]()
$630
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:00 pm -
2 stops10h 15m
Thu 11/128:40 pm -
2 stops16h 45m
Deal found 9/9![Southwest logo]()
$618
This WestJet deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:35 pm -
2 stops20h 43m
Sat 12/129:37 am -
2 stops26h 58m
Deal found 9/8![WestJet logo]()
$1,789
Last-minute flights from Montego Bay to ChicagoDiscover last-minute flight deals from Montego Bay to Chicago. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Montego Bay to Chicago. Data last updated September 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:16 pm -
1 stop14h 32m
Mon 9/286:59 am -
1 stop5h 54m
Deal found 9/8![American Airlines logo]()
$426
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.
Thu 10/13:42 pm -
1 stop8h 02m
Thu 10/86:40 pm -
1 stop19h 53m
Deal found 9/13![Frontier logo]()
$630
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:42 pm -
1 stop26h 09m
Thu 10/811:45 am -
2 stops27h 50m
Deal found 9/13![Multiple Airlines logo]()
$781
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:00 pm -
2 stops10h 15m
Thu 11/128:40 pm -
2 stops16h 45m
Deal found 9/9![Southwest logo]()
$618
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.
Wed 10/2112:18 pm -
1 stop9h 12m
Sat 10/246:59 pm -
1 stop16h 19m
Deal found 9/10![American Airlines logo]()
$366
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:30 pm -
2 stops19h 14m
Sat 10/246:21 pm -
2 stops18h 04m
Deal found 9/10![Air Canada logo]()
$409
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/2312:30 pm -
1 stop20h 30m
Fri 10/308:40 pm -
1 stop19h 40m
Deal found 9/8![Air Canada logo]()
$385
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates ” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:13 pm -
2 stops10h 47m
Fri 10/306:55 am -
1 stop9h 17m
Deal found 9/8![American Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:52 pm -
1 stop8h 40m
Fri 10/308:40 am -
Nonstop4h 08m
Deal found 9/8![United Airlines logo]()
$422
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.
Thu 10/2912:18 pm -
1 stop10h 42m
Tue 11/39:40 am -
Nonstop4h 12m
Deal found 9/10![American Airlines logo]()
$402
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 September 13, 2026.
Search for one-way flight options from Montego Bay to Chicago. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
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.
Wed 10/2812:50 pm -
1 stop24h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Air Canada logo]()
$204
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.
Mon 11/23:56 pm -
Nonstop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$209
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:43 pm -
1 stop27h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$212
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/82:20 pm -
1 stop30h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Air Canada logo]()
$214
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 2/2712:07 pm -
1 stop9h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$220
This Travelocity 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 Travelocity 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 9/11![Air Canada logo]()
$223
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:48 pm -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$224
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.
Sun 12/133:20 pm -
1 stop28h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Air Canada logo]()
$225
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.
Fri 9/253:42 pm -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Sun 10/43:42 pm -
1 stop17h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$229
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 9/273:42 pm -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$229
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.
Sat 10/103:48 pm -
1 stop17h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$230
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 September 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $353 (Trip.com) |
One-way from | $204 (Trip.com) |
Good round-trip deal | $540 or less |
Good one-way deal | $295 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 September 13, 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 - MDW Chicago Midway
MBJMDW
Montego Bay Sangster Intl
Fri 11/13
4:23 pm-11:47 pm
1 stop8h 24m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$229
Quickest round-trip
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Sat 11/7
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$249
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Fri 11/6
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$249
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Sun 3/7
2:48 pm-6:16 pm
Nonstop4h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$250
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Wed 3/10
3:20 pm-10:58 pm
1 stop8h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$250
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Thu 3/4
3:20 pm-10:58 pm
1 stop8h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$250
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Thu 11/12
1:07 pm-11:55 pm
1 stop11h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$253
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Wed 10/7
1:16 pm-8:38 pm
1 stop7h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Sat 12/12
6:12 pm-11:52 pm
1 stop6h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
Montego BayChicago
MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl
MBJORD
Montego Bay Sangster Intl
Mon 11/9
2:54 pm-6:20 pm
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
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 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 Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Montego Bay-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montego Bay-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Montego Bay-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Montego Bay-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Montego Bay-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Montego Bay to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Montego Bay with our price prediction graph.
MBJ-CHI
MBJ-ORD
MBJ-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Montego Bay to Chicago
MBJ-CHI
MBJ-ORD
MBJ-MDW
No data available for this route at this time. Please check back soon.
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 September 13, 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.
Boarding
7.4
Comfort
7.2
Crew
7.9
Food
6.4
Overall
7.1
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Boarding
7.4
Comfort
7.2
Crew
7.9
Food
6.4
Overall
7.1
Entertainment
6.8
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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Montego Bay and Chicago flights
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Top 3 airlines flying from Montego Bay to Chicago
Discover the top 3 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 September 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$281 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$281 | Average$548 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$281 | Average$417 | FlexibilityNo cancel fee | On-time71% |