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Montego Bay

$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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
May 18 — May 251
Mon 5/18
Mon 5/25
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 April 18, 2026.

This FlightHub deal was found by Cheapflights users on 4/16. 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.
Tue 5/56:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/16$304
This Frontier deal was found by Cheapflights users on 4/13. 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 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
Fri 5/81:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/13$308
This Southwest deal was found by Cheapflights users on 4/16. 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 7/267:50 am
MDW
-
MBJ
Nonstop3h 55m
Southwest
Thu 7/301:50 pm
MBJ
-
MDW
Nonstop4h 00m
Southwest
Deal found 4/16$318
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Mon 5/181:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/13$322
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:59 am
MDW
-
MBJ
1 stop24h 12m
Frontier
Mon 5/111:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/14$332
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia 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 stop21h 56m
Frontier
Deal found 4/14$335
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Mon 5/111:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/14$342
This Justfly.com deal was found by Cheapflights users on 4/14. 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 5/86:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Mon 5/111:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/14$344
This Justfly.com deal was found by Cheapflights users on 4/13. 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.
Wed 5/136:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/13$346
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:59 am
MDW
-
MBJ
1 stop24h 12m
Frontier
Sun 5/171:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/13$352

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 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$304
(FlightHub)

One-way from

$108
(Frontier)

Popular in

March

Cheapest in

October

Average price

$550

Good round-trip deal

$317 or less
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. 9% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Montego Bay Sangster Intl.
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 April 18, 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

Sat 6/20

6:00 am-12:21 pm

1 stop6h 21m

Montego Bay Sangster Intl

Thu 6/25

1:26 pm-10:11 pm

1 stop8h 45m

$452

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 4/28

6:00 am-11:35 am

1 stop5h 35m

Montego Bay Sangster Intl

Sun 5/3

3:20 pm-7:10 am

2 stops15h 50m

$467

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 8/12

6:30 am-12:55 pm

1 stop6h 25m

Montego Bay Sangster Intl

Wed 8/19

11:50 am-10:20 pm

2 stops10h 30m

$469

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/5

3:07 pm-12:11 pm

2 stops45h 04m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-10:02 pm

1 stop8h 46m

$484

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 9/2

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Sat 9/5

1:14 pm-9:46 pm

1 stop8h 32m

$513

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 6/5

6:23 am-3:34 pm

1 stop9h 11m

Montego Bay Sangster Intl

Wed 6/10

1:21 pm-10:17 pm

1 stop8h 56m

$513
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/25

10:10 am-2:00 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 8/1

1:15 pm-11:20 pm

2 stops10h 05m

$542

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 8/13

5:55 am-1:15 pm

2 stops7h 20m

Montego Bay Sangster Intl

Thu 8/20

2:15 pm-9:30 pm

1 stop7h 15m

$570

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/4

6:30 am-12:35 pm

1 stop6h 05m

Montego Bay Sangster Intl

Sat 7/11

1:15 pm-10:25 pm

2 stops9h 10m

$573

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/29

6:00 am-3:17 pm

1 stop9h 17m

Montego Bay Sangster Intl

Sat 5/2

2:10 pm-10:28 pm

1 stop8h 18m

$581

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
CheapTicketsDealPrice 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, 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.

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 April 18, 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.

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 18, 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
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,421 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,987 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 Frontier, Southwest, and Delta fly from Chicago Midway Airport to Montego Bay in about 5h 35m. The time it takes to get you to your destination can typically vary by up to 3h 59m. Chicago Midway Airport and Montego Bay are separated by a distance of 1709 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $341. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $395 and $518, respectively. Frontier is currently priced 48% below the average price you’ll pay for this route.

  • What are the cheapest flights from Chicago Midway Airport to Montego Bay?

    The cheapest flight price from Chicago Midway Airport to Montego Bay is $307. On average you can expect to pay $517. The most popular route, (Chicago Midway - Montego Bay Sangster Intl), can usually be booked for $318.

  • 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, 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.

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
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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 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$341Average$472FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$606FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$518Average$653FlexibilityNo cancel feeOn-time63%

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