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Montego Bay

$159+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Find 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 October 20, 2025.

This Delta deal was found by Cheapflights users on 10/19. 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 11/25:00 amMDW - MBJ
1 stop9h 34mDelta
Thu 11/63:45 pmMBJ - MDW
1 stop7h 29mDelta
Deal found 10/19$371
This Delta deal was found by Cheapflights users on 10/18. 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 11/46:00 amMDW - MBJ
1 stop7h 20mDelta
Thu 11/132:17 pmMBJ - MDW
1 stop10h 23mDelta
Deal found 10/18$396
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/88:42 pmMDW - MBJ
2 stops14h 28mMultiple Airlines
Thu 12/113:26 pmMBJ - MDW
1 stop29h 16mMultiple Airlines
Deal found 10/19$398
This Delta deal was found by Cheapflights users on 10/19. 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 11/176:00 amMDW - MBJ
1 stop5h 52mDelta
Mon 11/245:59 pmMBJ - MDW
1 stop6h 41mDelta
Deal found 10/19$408
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Thu 12/47:47 pmMDW - MBJ
1 stop18h 51mFrontier
Thu 12/113:26 pmMBJ - MDW
1 stop7h 46mFrontier
Deal found 10/20$428
This Delta deal was found by Cheapflights users on 10/19. 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 10/286:00 amMDW - MBJ
1 stop7h 20mDelta
Fri 10/311:32 pmMBJ - MDW
1 stop8h 42mDelta
Deal found 10/19$431
This Southwest deal was found by Cheapflights users on 10/18. 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 10/287:05 amMDW - MBJ
1 stop6h 40mSouthwest
Sun 11/23:55 pmMBJ - MDW
1 stop8h 05mSouthwest
Deal found 10/18$434
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/247:36 pmMDW - MBJ
2 stops15h 26mMultiple Airlines
Thu 11/272:43 pmMBJ - MDW
1 stop9h 00mMultiple Airlines
Deal found 10/19$435
This Southwest deal was found by Cheapflights users on 10/19. 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 10/266:25 amMDW - MBJ
1 stop5h 30mSouthwest
Fri 10/312:45 pmMBJ - MDW
1 stop6h 25mSouthwest
Deal found 10/19$447
This Priceline deal was found by Cheapflights users on 10/19. 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 11/236:05 amMDW - MBJ
1 stop8h 30mFrontier
Fri 11/284:30 pmMBJ - MDW
1 stop7h 13mFrontier
Deal found 10/19$453

Cheap 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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$363
(Delta)

One-way from

$159
(Kiwi.com)

Popular in

August

Cheapest in

October

Average price

$549
Provider with most accurate pricing for Chicago Midway-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Montego Bay Sangster Intl flights.
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From Chicago Midway to Montego Bay Sangster Intl
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One-way flight from Chicago Midway to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 20, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.

Fly from

Midway

Fly to

Montego Bay

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/27

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

Sat 1/31

12:45 pm-6:34 pm

1 stop6h 49m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 1/23

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

Wed 1/28

12:35 pm-9:46 pm

1 stop10h 11m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 11/2

5:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Thu 11/6

3:45 pm-10:14 pm

1 stop7h 29m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/10

9:30 am-8:25 pm

2 stops9h 55m

Montego Bay Sangster Intl

Sat 1/17

8:00 am-6:34 pm

2 stops11h 34m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/23

9:30 am-8:25 pm

2 stops9h 55m

Montego Bay Sangster Intl

Sat 2/28

8:00 am-9:46 pm

1 stop14h 46m

$409

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/8

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/11

2:00 pm-9:00 pm

1 stop8h 00m

$437

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/21

9:30 am-8:25 pm

2 stops9h 55m

Montego Bay Sangster Intl

Sat 2/28

8:00 am-9:46 pm

1 stop14h 46m

$461

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 2/5

6:00 am-2:22 pm

1 stop7h 22m

Montego Bay Sangster Intl

Mon 2/9

3:46 pm-11:25 pm

1 stop8h 39m

$490

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/10

6:40 am-3:00 pm

1 stop7h 20m

Montego Bay Sangster Intl

Fri 1/16

2:00 pm-10:25 pm

1 stop9h 25m

$490

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 3/10

6:00 am-11:40 am

1 stop5h 40m

Montego Bay Sangster Intl

Wed 3/11

1:05 pm-9:46 pm

1 stop8h 41m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 20 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $384). Flying from Chicago Midway Airport to Montego Bay in March is currently the most expensive (average of $594). 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 October 20, 2025.

It’s optimal to fly from Chicago Midway Airport to Montego Bay in the evening. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight at noon.

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 October 20, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier from Chicago Midway Airport to Montego Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,976 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,130 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Delta fly from Chicago Midway Airport to Montego Bay in about 8h 15m. 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 $370. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $395 and $549, respectively. Frontier is currently priced 45% 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $384). Flying from Chicago Midway Airport to Montego Bay in March is currently the most expensive (average of $594). 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
Whitehouse
Lucea

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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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$436FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$630FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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