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Montego Bay

$197+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheap flight deals from Midway to Montego Bay

Cheapest flights from Midway to Montego Bay
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 August 1, 2026.

This Delta deal was found by Cheapflights users on 7/29. 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.
Sun 11/156:00 am
MDW
-
MBJ
1 stop9h 35m
Delta
Tue 11/243:40 pm
MBJ
-
MDW
1 stop8h 16m
Delta
Deal found 7/29$442
This Southwest deal was found by Cheapflights users on 7/29. 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 9/231:55 pm
MBJ
-
MDW
1 stop6h 55m
Southwest
Deal found 7/29$444
This Delta deal was found by Cheapflights users on 7/29. 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.
Mon 11/96:00 am
MDW
-
MBJ
1 stop9h 35m
Delta
Mon 11/236:00 pm
MBJ
-
MDW
2 stops16h 42m
Delta
Deal found 7/29$447
This Southwest deal was found by Cheapflights users on 7/27. 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.
Tue 9/226:30 am
MDW
-
MBJ
1 stop6h 25m
Southwest
Tue 9/291:55 pm
MBJ
-
MDW
1 stop6h 55m
Southwest
Deal found 7/27$455
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:10 am
MDW
-
MBJ
1 stop7h 15m
Southwest
Sun 9/2012:45 pm
MBJ
-
MDW
1 stop9h 45m
Southwest
Deal found 7/30$480
This Frontier deal was found by Cheapflights users on 7/31. 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 9/146:25 am
MDW
-
MBJ
1 stop8h 02m
Frontier
Mon 9/213:42 pm
MBJ
-
MDW
1 stop8h 02m
Frontier
Deal found 7/31$481
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Wed 11/1112:03 pm
MDW
-
MBJ
1 stop25h 21m
Frontier
Sat 11/143:39 pm
MBJ
-
MDW
1 stop7h 14m
Frontier
Deal found 7/31$483
This Delta deal was found by Cheapflights users on 7/27. 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.
Tue 10/276:04 am
MDW
-
MBJ
1 stop6h 56m
Delta
Sun 11/15:44 pm
MBJ
-
MDW
2 stops20h 03m
Delta
Deal found 7/27$485
This Frontier deal was found by Cheapflights users on 7/30. 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.
Sun 9/136:25 am
MDW
-
MBJ
1 stop8h 02m
Frontier
Sun 9/203:42 pm
MBJ
-
MDW
1 stop8h 02m
Frontier
Deal found 7/30$486
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:05 am
MDW
-
MBJ
1 stop7h 20m
Southwest
Fri 12/111:50 pm
MBJ
-
MDW
2 stops9h 50m
Southwest
Deal found 7/27$490

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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$442
(Delta)

One-way from

$197
(Delta)

Popular in

March

Cheapest in

December

Average price

$675
Provider with most accurate pricing for Chicago Midway-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Montego Bay Sangster Intl flights.
Search Deals
From Chicago Midway to Montego Bay Sangster Intl
Search Deals
One-way flight from Chicago Midway to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($104 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

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 August 1, 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

Price

Cheapest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/22

6:30 am-12:55 pm

1 stop6h 25m

Montego Bay Sangster Intl

Tue 9/29

12:55 pm-9:25 pm

1 stop8h 30m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/12

5:55 am-12:25 pm

1 stop6h 30m

Montego Bay Sangster Intl

Sat 9/19

11:40 am-8:35 pm

1 stop8h 55m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/22

6:30 am-12:55 pm

1 stop6h 25m

Montego Bay Sangster Intl

Fri 10/30

12:50 pm-10:00 pm

1 stop9h 10m

$480
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/8

6:15 am-11:55 am

1 stop5h 40m

Montego Bay Sangster Intl

Sat 9/12

1:25 pm-8:35 pm

1 stop7h 10m

$512

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 9/11

7:50 pm-12:25 pm

2 stops16h 35m

Montego Bay Sangster Intl

Fri 9/18

2:15 pm-10:25 pm

2 stops8h 10m

$528

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 8/28

7:55 pm-11:20 am

2 stops15h 25m

Montego Bay Sangster Intl

Fri 9/4

2:15 pm-10:45 pm

1 stop8h 30m

$532

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/13

5:00 am-1:00 pm

1 stop8h 00m

Montego Bay Sangster Intl

Sun 9/20

12:45 pm-8:45 am

2 stops20h 00m

$556

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 9/11

7:55 pm-12:50 pm

2 stops16h 55m

Montego Bay Sangster Intl

Tue 9/15

12:55 pm-9:00 pm

1 stop8h 05m

$565

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 8/24

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Thu 8/27

1:09 pm-10:36 pm

1 stop9h 27m

$576
Cheapest one-way
Quickest one-way

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/29

6:05 am-11:48 am

1 stop5h 43m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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 March is currently the most expensive (average of $1,144). 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.

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 August 1, 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.
Southwest
8.0
Very good
4,226 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Southwest
8.0
Very good
4,226 reviews
Southwest
8.0
Very good
4,226 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Delta
7.8
Good
8,494 reviews
Southwest
8.0
Very good
4,226 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Frontier
5.6
Fair
2,746 reviews
Southwest
8.0
Very good
4,226 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.

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.

  • What airport do you fly into for flights to Montego Bay from Chicago Midway?

    Montego Bay Sangster Intl (MBJ), located 2.3 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Montego Bay. 3 airlines have flights to Sangster Intl from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Montego Bay Sangster Intl should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Montego Bay?

    Airlines like Southwest fly from Chicago Midway Airport to Montego Bay in about 6h 25m. The time it takes to get you to your destination can typically vary by up to . Chicago Midway Airport and Montego Bay are separated by a distance of 1709 mi.

  • What are the cheapest airlines flying from Chicago Midway Airport to Montego Bay round-trip?

    Flying on Frontier is currently your cheapest option to Montego Bay, with prices starting at $172. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $395 and $467, respectively. Frontier is currently priced 74% below the average price you’ll pay for this route.

  • Can I find deals for flights from Midway to Montego Bay that include hotel bookings?

    Yes. In addition to deals on Midway to Montego Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Montego Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Montego Bay.

  • Can I find deals for business class flights from Midway to Montego Bay?

    Yes. Cheapflights offers flight deals from Midway to Montego Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 March is currently the most expensive (average of $1,144). 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.

See more FAQs

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
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Alternative routes for Midway to Montego Bay

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Montego Bay flights
O'Hare Intl to Kingston flights
Midway to Kingston flights

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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$172Average$493FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$658FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$467Average$653FlexibilityNo cancel feeOn-time63%

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