$108+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
May 30 — Jun 61
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Montego Bay with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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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 April 30, 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 April 30, 2026.
This Southwest deal was found by Cheapflights users on 4/26. 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 7/410:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Tue 7/71:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/26![Southwest logo]()
$318
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$328
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 6/21:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$338
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$348
This Priceline deal was found by Cheapflights users on 4/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 5/131:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/27![Frontier logo]()
$349
This Frontier deal was found by Cheapflights users on 4/26. 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 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 5/301:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/26![Frontier logo]()
$362
This Orbitz deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Wed 8/51:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 4/27![Frontier logo]()
$372
This FlightHub deal was found by Cheapflights users on 4/27. 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 6/412:27 pm
MDW
- MBJ
1 stop23h 44m
Frontier
Mon 6/81:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/27![Frontier logo]()
$390
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Mon 6/81:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$392
This Priceline deal was found by Cheapflights users on 4/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$393
This deal was found by Cheapflights users on 4/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Tue 7/71:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 4/26![Frontier logo]()
$406
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 April 30, 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 April 30, 2026.
This Priceline deal was found by Cheapflights users on 4/29. 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.
Thu 7/96:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Sat 7/251:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 4/29![Frontier logo]()
$432
This Southwest deal was found by Cheapflights users on 4/27. 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 7/1110:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 7/1512:35 pm
MBJ
- MDW
1 stop9h 00m
Southwest
Deal found 4/27![Southwest logo]()
$443
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Wed 9/231:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 4/29![Delta logo]()
$462
This Southwest deal was found by Cheapflights users on 4/29. 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.
Fri 7/247:00 am
MDW
- MBJ
1 stop7h 55m
Southwest
Wed 7/291:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/29![Southwest logo]()
$450
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Sat 9/261:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 4/27![Delta logo]()
$513
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 7/2210:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Fri 7/311:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/28![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 4/26. 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 6/295:10 am
MDW
- MBJ
2 stops9h 45m
Southwest
Sun 7/52:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/26![Southwest logo]()
$490
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 7/2911:45 am
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 4/29![Southwest logo]()
$501
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 9/195:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Wed 9/2312:55 pm
MBJ
- MDW
2 stops8h 55m
Southwest
Deal found 4/29![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 4/25. 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 6/207:35 pm
MDW
- MBJ
2 stops19h 20m
Southwest
Wed 6/243:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 4/25![Southwest logo]()
$595
Last-minute flights from Midway to Montego BayDiscover last-minute flight deals from Midway to Montego Bay. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Montego Bay. Data last updated April 30, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$328
This Priceline deal was found by Cheapflights users on 4/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 5/131:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/27![Frontier logo]()
$349
This Priceline deal was found by Cheapflights users on 4/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/28![Frontier logo]()
$393
This Frontier deal was found by Cheapflights users on 4/26. 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.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Thu 5/141:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/26![Frontier logo]()
$412
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$348
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 6/21:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/29![Frontier logo]()
$338
This Frontier deal was found by Cheapflights users on 4/26. 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 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 5/301:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/26![Frontier logo]()
$362
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 6/91:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 4/29![Frontier logo]()
$422
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 April 30, 2026.
Search for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Priceline deal was found by Cheapflights users on 4/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/27![Frontier logo]()
$108
This Priceline deal was found by Cheapflights users on 4/29. 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.
Thu 5/1412:19 pm
MDW
- MBJ
1 stop23h 52m
Frontier
Deal found 4/29![Frontier logo]()
$135
This Southwest deal was found by Cheapflights users on 4/26. 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 7/2410:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 4/26![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 7/2110:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 4/29![Southwest logo]()
$148
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/27![Frontier logo]()
$152
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/30![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/29![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
MDW
- MBJ
1 stop30h 21m
Frontier
Deal found 4/30![Frontier logo]()
$174
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Deal found 4/29![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/286:00 am
MDW
- MBJ
1 stop30h 21m
Frontier
Deal found 4/30![Frontier logo]()
$178
This FlightHub deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:04 pm
MDW
- MBJ
1 stop24h 07m
Frontier
Deal found 4/28![Frontier logo]()
$181
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 April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (Southwest) |
One-way from | $108 (Priceline) |
Popular in | March |
Cheapest in | October |
Average price | $547 |
Good round-trip deal | $517 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 April 30, 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
Cheapest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 7/9
6:00 am-12:27 pm
1 stop6h 27m
Montego Bay Sangster Intl
Sat 7/25
1:32 pm-10:08 pm
1 stop8h 36m
$432
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 7/11
10:10 am-2:00 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Wed 7/15
12:35 pm-9:35 pm
1 stop9h 00m
$443
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 7/24
7:00 am-2:55 pm
1 stop7h 55m
Montego Bay Sangster Intl
Wed 7/29
1:50 pm-5:50 pm
Nonstop4h 00m
$450
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 9/19
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Wed 9/23
1:25 pm-9:46 pm
1 stop8h 21m
$462
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 7/22
10:05 am-1:55 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Fri 7/31
1:50 pm-5:50 pm
Nonstop4h 00m
$481
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 6/29
5:10 am-2:55 pm
2 stops9h 45m
Montego Bay Sangster Intl
Sun 7/5
2:30 pm-6:35 pm
Nonstop4h 05m
$490
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 7/22
10:05 am-1:55 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Wed 7/29
11:45 am-7:50 pm
2 stops8h 05m
$501
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 9/21
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Sat 9/26
1:25 pm-9:46 pm
1 stop8h 21m
$513
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 9/19
5:55 am-12:25 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 9/23
12:55 pm-9:50 pm
2 stops8h 55m
$570
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 6/20
7:35 pm-2:55 pm
2 stops19h 20m
Montego Bay Sangster Intl
Wed 6/24
3:55 pm-11:50 pm
1 stop7h 55m
$595
Showing 1-10 of 20 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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $525). Flying from Chicago Midway Airport to Montego Bay in March is currently the most expensive (average of $984). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago Midway Airport to Montego Bay?
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 April 30, 2026.
Read reviews from past customers who have flown Southwest,Delta, andFrontier 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
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 30, 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$472 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$564 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$468 | Average$653 | FlexibilityNo cancel fee | On-time63% |