$175+ Cheap flights from Midway (MDW) to Montego Bay (MBJ)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Oct 14 — Oct 211
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
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Montego Bay
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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 September 14, 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 September 14, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:42 pm -
1 stop19h 26m
Sun 11/84:43 pm -
1 stop26h 04m
Deal found 9/9![Frontier logo]()
$431
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:46 pm -
1 stop17h 16m
Mon 10/53:42 pm -
1 stop8h 01m
Deal found 9/12![Frontier logo]()
$453
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:04 am -
1 stop9h 31m
Tue 11/33:26 pm -
1 stop8h 07m
Deal found 9/10![Delta logo]()
$462
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:05 am -
1 stop5h 43m
Fri 10/234:42 pm -
2 stops20h 05m
Deal found 9/10![Delta logo]()
$467
This Justfly.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:46 pm -
1 stop17h 16m
Sun 9/203:42 pm -
1 stop8h 02m
Deal found 9/14![Frontier logo]()
$472
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.
Mon 11/305:20 am -
2 stops8h 25m
Tue 12/83:45 pm -
1 stop6h 30m
Deal found 9/9![Southwest logo]()
$485
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:05 am -
1 stop6h 56m
Wed 10/211:16 pm -
2 stops20h 16m
Deal found 9/10![Delta logo]()
$490
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:04 pm -
1 stop22h 04m
Mon 12/142:25 pm -
1 stop23h 34m
Deal found 9/13![Frontier logo]()
$492
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.
Sat 10/106:21 am -
1 stop8h 12m
Thu 10/223:48 pm -
1 stop7h 55m
Deal found 9/10![Frontier logo]()
$494
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.
Thu 10/16:46 pm -
1 stop19h 41m
Mon 10/53:42 pm -
1 stop8h 01m
Deal found 9/10![Frontier logo]()
$495
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 September 14, 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 September 14, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:05 am -
1 stop5h 43m
Fri 10/234:42 pm -
2 stops20h 05m
Deal found 9/10![Delta logo]()
$467
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.
Mon 11/305:20 am -
2 stops8h 25m
Tue 12/83:45 pm -
1 stop6h 30m
Deal found 9/9![Southwest logo]()
$485
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:04 am -
1 stop9h 31m
Tue 11/33:26 pm -
1 stop8h 07m
Deal found 9/13![Delta logo]()
$482
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.
Sun 11/298:45 pm -
2 stops16h 40m
Tue 12/83:45 pm -
1 stop6h 30m
Deal found 9/9![Southwest logo]()
$490
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:10 am -
1 stop6h 45m
Wed 10/2812:00 pm -
1 stop7h 45m
Deal found 9/13![Southwest logo]()
$542
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:04 am -
1 stop5h 47m
Thu 10/221:16 pm -
1 stop9h 17m
Deal found 9/10![Delta logo]()
$563
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:05 am -
2 stops8h 40m
Wed 12/161:00 pm -
2 stops10h 40m
Deal found 9/10![Southwest logo]()
$542
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:30 pm -
2 stops18h 30m
Thu 10/2212:00 pm -
2 stops11h 55m
Deal found 9/10![Southwest logo]()
$543
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.
Mon 10/55:00 am -
1 stop6h 50m
Thu 10/812:00 pm -
2 stops11h 15m
Deal found 9/12![Southwest logo]()
$559
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.
Tue 11/35:20 am -
1 stop6h 30m
Sun 11/81:00 pm -
1 stop11h 05m
Deal found 9/9![Southwest logo]()
$600
Last-minute flights from Midway to Montego BayDiscover last-minute flight deals from Midway to Montego Bay. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Montego Bay. Data last updated September 14, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:46 pm -
1 stop17h 16m
Sun 9/203:42 pm -
1 stop8h 02m
Deal found 9/14![Frontier logo]()
$472
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.
Thu 10/16:46 pm -
1 stop19h 41m
Mon 10/53:42 pm -
1 stop8h 01m
Deal found 9/10![Frontier logo]()
$495
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:46 pm -
1 stop17h 16m
Mon 10/53:42 pm -
1 stop8h 01m
Deal found 9/12![Frontier logo]()
$453
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:05 am -
1 stop5h 43m
Fri 10/234:42 pm -
2 stops20h 05m
Deal found 9/10![Delta logo]()
$467
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:05 am -
1 stop5h 43m
Wed 10/211:16 pm -
1 stop9h 17m
Deal found 9/10![Delta logo]()
$485
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.
Sat 10/106:21 am -
1 stop8h 12m
Thu 10/223:48 pm -
1 stop7h 55m
Deal found 9/10![Frontier logo]()
$494
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.
Thu 10/221:12 pm -
2 stops25h 21m
Mon 10/263:48 pm -
1 stop7h 55m
Deal found 9/10![Frontier logo]()
$503
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:12 pm -
2 stops25h 21m
Mon 10/263:48 pm -
1 stop7h 55m
Deal found 9/10![Frontier logo]()
$512
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.
Fri 10/236:15 am -
1 stop8h 18m
Sun 10/253:48 pm -
1 stop7h 55m
Deal found 9/10![Frontier logo]()
$515
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:04 am -
1 stop9h 31m
Tue 11/33:26 pm -
1 stop8h 07m
Deal found 9/10![Delta logo]()
$462
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 September 14, 2026.
Search for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$175
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:16 am -
1 stop8h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$176
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.
Mon 11/96:16 am -
1 stop7h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$177
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.
Sun 10/116:24 am -
1 stop8h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$179
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$182
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:46 pm -
1 stop17h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$192
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 9/186:46 pm -
1 stop17h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$196
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:20 pm -
2 stops26h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$199
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$207
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:44 pm -
2 stops21h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$213
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 September 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $431 (FlightHub) |
One-way from | $175 (Super.com) |
Popular in | November |
Cheapest in | December |
Average price | $585 |
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 7,457,451 searches. Data last updated September 14, 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 Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 12/8
6:00 am-4:57 pm
1 stop9h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 9/28
5:55 am-1:15 pm
2 stops7h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
Quickest round-trip
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 11/10
6:00 am-12:51 pm
1 stop5h 51m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 10/6
6:04 am-1:00 pm
1 stop6h 56m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 11/9
6:44 pm-4:57 pm
2 stops21h 13m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 10/11
6:44 pm-3:27 pm
2 stops20h 43m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$223
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Fri 11/13
6:44 pm-4:57 pm
2 stops21h 13m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$223
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Wed 11/11
5:13 pm-12:30 pm
2 stops18h 17m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$237
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 12/13
2:04 pm-1:08 pm
1 stop22h 04m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$244
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sat 9/26
6:05 am-3:44 pm
1 stop9h 39m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$263
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 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 Accuracy- | Trust Score*1 star | |
| 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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $493). Flying from Chicago Midway Airport to Montego Bay in November is currently the most expensive (average of $924). 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?
Airfare is below average for this route at the moment.
Chicago Midway Airport to Montego Bay flights typically cost between $554 and $658 in November.The cheapest round-trip price found within the last 5 days was $431 on Frontier (Nov 5-Nov 8).
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 September 14, 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.
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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Top 3 airlines flying from Midway to Montego Bay
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$493 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$658 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |