$118+ Cheap flights from Midway (MDW) to Montego Bay (MBJ)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Apr 1 — Apr 81
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 Midway to Montego BayExplore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 2, 2026.
Explore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 2, 2026.
This Southwest deal was found by Cheapflights users on 2/28. 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.
Fri 6/510:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Mon 6/81:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 2/28![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 2/26. 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.
Sat 5/99:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Fri 5/152:25 pm
MBJ
- MDW
2 stops9h 05m
Southwest
Deal found 2/26![Southwest logo]()
$378
This Orbitz deal was found by Cheapflights users on 2/28. 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.
Tue 5/269:16 pm
MDW
- MBJ
1 stop15h 26m
Frontier
Tue 6/21:59 pm
MBJ
- MDW
1 stop17h 01m
Frontier
Deal found 2/28![Frontier logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- MBJ
2 stops22h 01m
Multiple Airlines
Sat 5/21:17 pm
MBJ
- MDW
1 stop8h 57m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/27:34 pm
MDW
- MBJ
2 stops16h 42m
Multiple Airlines
Sat 5/91:22 pm
MBJ
- MDW
1 stop8h 57m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 2/28. 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.
Sun 4/511:10 am
MDW
- MBJ
Nonstop3h 45m
Southwest
Thu 4/912:35 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 2/28![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:00 am
MDW
- MBJ
1 stop6h 55m
Southwest
Wed 4/2212:15 pm
MBJ
- MDW
1 stop9h 10m
Southwest
Deal found 3/1![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 2/28. 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.
Sat 5/239:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Fri 5/292:25 pm
MBJ
- MDW
1 stop9h 40m
Southwest
Deal found 2/28![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 2/26. 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.
Mon 4/207:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Thu 4/2312:35 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 2/26![Southwest logo]()
$419
Best flights from Midway to Montego BayDiscover carefully curated flight deals from Midway to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 2, 2026.
Discover carefully curated flight deals from Midway to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 2, 2026.
This Southwest deal was found by Cheapflights users on 2/27. 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.
Sun 3/811:10 am
MDW
- MBJ
Nonstop3h 45m
Southwest
Wed 3/1112:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 2/27![Southwest logo]()
$428
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/196:00 am
MDW
- MBJ
1 stop6h 54m
Delta
Thu 4/234:32 pm
MBJ
- MDW
2 stops16h 15m
Delta
Deal found 3/1![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 2/27. 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.
Wed 4/296:00 am
MDW
- MBJ
1 stop6h 54m
Delta
Sat 5/22:10 pm
MBJ
- MDW
1 stop8h 18m
Delta
Deal found 2/27![Delta logo]()
$513
This Delta deal was found by Cheapflights users on 2/25. 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.
Tue 3/176:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Mon 3/2311:15 am
MBJ
- MDW
2 stops21h 38m
Delta
Deal found 2/25![Delta logo]()
$518
This Southwest deal was found by Cheapflights users on 2/27. 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.
Thu 3/129:00 pm
MDW
- MBJ
2 stops17h 30m
Southwest
Sun 3/1512:30 pm
MBJ
- MDW
Nonstop4h 20m
Southwest
Deal found 2/27![Southwest logo]()
$595
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/2211:10 am
MDW
- MBJ
Nonstop3h 45m
Southwest
Wed 3/2512:55 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 3/1![Southwest logo]()
$598
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/66:35 am
MDW
- MBJ
1 stop7h 55m
Southwest
Tue 3/1012:55 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 3/1![Southwest logo]()
$612
This Southwest deal was found by Cheapflights users on 2/25. 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 3/116:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Tue 3/1712:55 pm
MBJ
- MDW
2 stops18h 50m
Southwest
Deal found 2/25![Southwest logo]()
$617
This Southwest deal was found by Cheapflights users on 2/25. 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.
Sat 3/146:30 am
MDW
- MBJ
1 stop7h 25m
Southwest
Sat 3/212:20 pm
MBJ
- MDW
Nonstop4h 15m
Southwest
Deal found 2/25![Southwest logo]()
$630
This Southwest deal was found by Cheapflights users on 2/26. 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.
Sat 3/218:45 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 3/2512:55 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 2/26![Southwest logo]()
$647
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/186:00 am
MDW
- MBJ
1 stop5h 55m
Southwest
Mon 3/233:30 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 3/1![Southwest logo]()
$675
Last-minute flights from Midway to Montego BayDiscover last-minute flight deals from Midway to Montego Bay. Data last updated March 2, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Montego Bay. Data last updated March 2, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/27. 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.
Sun 3/19:20 pm
MDW
- MBJ
2 stops16h 55m
Southwest
Sat 3/73:20 pm
MBJ
- MDW
Nonstop4h 15m
Southwest
Deal found 2/27![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/26:50 am
MDW
- MBJ
1 stop6h 20m
Southwest
Mon 3/93:30 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 3/1![Southwest logo]()
$512
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/56:35 am
MDW
- MBJ
1 stop7h 55m
Southwest
Sat 3/73:20 pm
MBJ
- MDW
Nonstop4h 15m
Southwest
Deal found 3/1![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:45 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 3/1112:55 pm
MBJ
- MDW
1 stop9h 45m
Southwest
Deal found 3/1![Southwest logo]()
$468
This CheapOair deal was found by Cheapflights users on 2/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:00 am
MDW
- MBJ
1 stop8h 17m
Frontier
Sat 3/143:32 pm
MBJ
- MDW
1 stop28h 15m
Frontier
Deal found 2/26![Frontier logo]()
$497
This Southwest deal was found by Cheapflights users on 2/27. 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.
Sun 3/811:10 am
MDW
- MBJ
Nonstop3h 45m
Southwest
Wed 3/1112:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 2/27![Southwest logo]()
$428
This Delta deal was found by Cheapflights users on 2/28. 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.
Mon 3/96:07 pm
MDW
- MBJ
1 stop15h 53m
Delta
Tue 3/1711:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Deal found 2/28![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 2/25. 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.
Mon 3/96:07 pm
MDW
- MBJ
1 stop15h 53m
Delta
Wed 3/184:49 pm
MBJ
- MDW
2 stops19h 40m
Delta
Deal found 2/25![Delta logo]()
$457
This Southwest deal was found by Cheapflights users on 2/26. 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 3/139:40 pm
MDW
- MBJ
1 stop13h 10m
Southwest
Sun 3/1512:30 pm
MBJ
- MDW
Nonstop4h 20m
Southwest
Deal found 2/26![Southwest logo]()
$502
This Delta deal was found by Cheapflights users on 2/25. 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.
Tue 3/176:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Thu 3/264:49 pm
MBJ
- MDW
1 stop17h 07m
Delta
Deal found 2/25![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 2/28. 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.
Sun 3/2211:10 am
MDW
- MBJ
Nonstop3h 45m
Southwest
Wed 3/2512:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 2/28![Southwest logo]()
$503
One-way flights from Midway to Montego BaySearch for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated March 2, 2026.
Search for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated March 2, 2026.
This Southwest deal was found by Cheapflights users on 2/27. 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.
Sun 4/511:10 am
MDW
- MBJ
Nonstop3h 45m
Southwest
Deal found 2/27![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 2/27. 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 5/117:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Deal found 2/27![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 2/27. 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.
Sat 4/119:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 2/27![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 2/28. 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.
Sat 3/78:45 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 2/28![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- MBJ
2 stops29h 05m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$151
This Priceline deal was found by Cheapflights users on 2/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- MBJ
1 stop6h 42m
Frontier
Deal found 2/26![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/272:15 pm
MDW
- MBJ
2 stops22h 01m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/112:56 pm
MDW
- MBJ
2 stops20h 09m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 2/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:15 pm
MDW
- MBJ
2 stops22h 01m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$156
This Priceline deal was found by Cheapflights users on 2/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:16 pm
MDW
- MBJ
1 stop15h 26m
Frontier
Deal found 2/26![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
- MBJ
2 stops30h 16m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$161
Find flight deals from Midway to Montego Bay
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 March 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $378 (Southwest) |
One-way from | $118 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $882 |
Good round-trip deal | $660 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway 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 2,558,603 searches. Data last updated March 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 3/8
11:10 am-2:55 pm
Nonstop3h 45m
Montego Bay Sangster Intl
Wed 3/11
12:55 pm-8:50 pm
1 stop7h 55m
$428
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 4/19
6:00 am-12:54 pm
1 stop6h 54m
Montego Bay Sangster Intl
Thu 4/23
4:32 pm-8:47 am
2 stops16h 15m
$457
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 4/29
6:00 am-12:54 pm
1 stop6h 54m
Montego Bay Sangster Intl
Sat 5/2
2:10 pm-10:28 pm
1 stop8h 18m
$513
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 3/17
6:00 am-3:28 pm
1 stop9h 28m
Montego Bay Sangster Intl
Mon 3/23
11:15 am-8:53 am
2 stops21h 38m
$518
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 3/12
9:00 pm-2:30 pm
2 stops17h 30m
Montego Bay Sangster Intl
Sun 3/15
12:30 pm-4:50 pm
Nonstop4h 20m
$595
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 3/22
11:10 am-2:55 pm
Nonstop3h 45m
Montego Bay Sangster Intl
Wed 3/25
12:55 pm-10:40 pm
1 stop9h 45m
$598
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 3/6
6:35 am-3:30 pm
1 stop7h 55m
Montego Bay Sangster Intl
Tue 3/10
12:55 pm-10:40 pm
1 stop9h 45m
$612
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 3/11
6:30 am-2:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Tue 3/17
12:55 pm-7:45 am
2 stops18h 50m
$617
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 3/14
6:30 am-1:55 pm
1 stop7h 25m
Montego Bay Sangster Intl
Sat 3/21
2:20 pm-6:35 pm
Nonstop4h 15m
$630
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 3/21
8:45 am-12:35 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Wed 3/25
12:55 pm-10:40 pm
1 stop9h 45m
$647
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Midway 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 Midway to Montego Bay in March.
| 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 Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-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 Midway Airport-Montego Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Montego Bay flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-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 Midway Airport-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 Midway to Montego Bay
Have a flexible travel schedule? Discover the best time to fly to Montego Bay from Midway with our price prediction graph.
MDW-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Montego Bay
What is the cheapest month to book a flight from Chicago Midway Airport to Montego Bay?
Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $384). Flying from Chicago Midway Airport to Montego Bay in November is currently the most expensive (average of $580). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to MBJ?
Find hourly flight availability from Midway to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 2, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Montego Bay as you normally would.
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 March 2, 2026.
Read reviews from past customers who have flown Southwest, Delta, and Frontier from Chicago Midway Airport 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
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Related info for your journey
Find useful and relevant information for your journey from Midway 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 March 2, 2026.
Midway and Montego Bay flights
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Top 3 airlines flying from Midway to Montego Bay
Discover the top 3 airlines that operate flights from Midway 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 2,558,603 searches. Data last updated March 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$446 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$606 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$518 | Average$693 | FlexibilityNo cancel fee | On-time63% |