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Montego Bay

$128+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Feb 10 — Feb 171
Di 2/10
Di 2/17
1 adult, Economy
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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 Januar 11, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$396
(Delta)

One-way from

$128
(Trip.com)

Popular in

August

Cheapest in

October

Average price

$666

Good round-trip deal

$476 or less
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
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Highest demand for flights based on searches. 4% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago Midway to Montego Bay Sangster Intl.
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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 Januar 11, 2026.

This Delta deal was found by Cheapflights users on 1/8. 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.
Mi 4/156:30 amMDW - MBJ
1 stop6h 46mDelta
Mi 4/222:40 pmMBJ - MDW
1 stop7h 49mDelta
Deal found 1/8$396
This Mytrip deal was found by Cheapflights users on 1/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 2/126:25 amMDW - MBJ
1 stop6h 28mFrontier
Mo 2/1610:05 amMBJ - MDW
1 stop13h 24mFrontier
Deal found 1/9$398
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
Fr 1/305:01 pmMDW - MBJ
1 stop19h 29mMultiple Airlines
Mo 2/212:57 pmMBJ - MDW
2 stops10h 22mMultiple Airlines
Deal found 1/8$408
This Delta deal was found by Cheapflights users on 1/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 1/266:00 amMDW - MBJ
1 stop5h 54mDelta
Fr 2/64:45 pmMBJ - MDW
1 stop6h 37mDelta
Deal found 1/9$416
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 2/136:48 pmMDW - MBJ
1 stop14h 51mMultiple Airlines
Di 2/171:00 pmMBJ - MDW
2 stops31h 07mMultiple Airlines
Deal found 1/10$421
This Frontier deal was found by Cheapflights users on 1/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 2/159:04 pmMDW - MBJ
1 stop10h 56mFrontier
Sa 2/2110:40 amMBJ - MDW
1 stop11h 53mFrontier
Deal found 1/9$426
This Frontier deal was found by Cheapflights users on 1/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 2/126:25 amMDW - MBJ
1 stop6h 28mFrontier
So 2/1510:32 amMBJ - MDW
1 stop10h 27mFrontier
Deal found 1/9$429
This Delta deal was found by Cheapflights users on 1/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 2/176:00 amMDW - MBJ
1 stop8h 19mDelta
Di 2/244:44 pmMBJ - MDW
1 stop6h 49mDelta
Deal found 1/11$436
This Delta deal was found by Cheapflights users on 1/10. 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.
Mi 2/46:00 amMDW - MBJ
1 stop8h 20mDelta
Mi 2/112:19 pmMBJ - MDW
2 stops19h 35mDelta
Deal found 1/10$441
This Southwest deal was found by Cheapflights users on 1/9. 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.
Mo 4/209:15 pmMDW - MBJ
2 stops16h 10mSouthwest
Fr 4/242:25 pmMBJ - MDW
1 stop9h 15mSouthwest
Deal found 1/9$443
This Mytrip deal was found by Cheapflights users on 1/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 2/197:30 amMDW - MBJ
2 stops24h 20mFrontier
So 2/2210:32 amMBJ - MDW
2 stops27h 36mFrontier
Deal found 1/9$444
This Delta deal was found by Cheapflights users on 1/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 1/246:25 amMDW - MBJ
1 stop7h 55mDelta
Do 1/2912:38 pmMBJ - MDW
1 stop10h 44mDelta
Deal found 1/9$446

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 Januar 11, 2026.
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

So 5/3

6:30 am-1:16 pm

1 stop6h 46m

Montego Bay Sangster Intl

Di 5/5

12:55 pm-10:29 pm

1 stop9h 34m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

So 2/1

5:30 am-1:00 pm

1 stop6h 30m

Montego Bay Sangster Intl

Do 2/5

1:30 pm-9:10 pm

1 stop8h 40m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mo 2/9

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Do 2/12

12:20 pm-5:45 pm

1 stop6h 25m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

So 2/15

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

Mi 2/18

4:44 pm-10:31 pm

1 stop6h 47m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Di 2/10

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Fr 2/13

4:44 pm-10:31 pm

1 stop6h 47m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

So 2/15

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

Do 2/19

4:44 pm-10:31 pm

1 stop6h 47m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mo 1/26

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Di 2/3

12:38 pm-10:22 pm

1 stop10h 44m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Di 2/17

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Di 2/24

2:19 pm-10:33 pm

1 stop9h 14m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

So 2/8

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Mi 2/11

4:45 pm-10:22 pm

1 stop6h 37m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mi 2/4

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Do 2/12

12:20 pm-10:31 pm

1 stop11h 11m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 23 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Montego Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $595). 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 Januar 11, 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.

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 Januar 11, 2026.
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
4,254 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,035 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,057 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 and Southwest fly from Chicago Midway Airport to Montego Bay in about 6h 30m. The time it takes to get you to your destination can typically vary by up to 16m. 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 $549, 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 $459. On average you can expect to pay $507. The most popular route, (Chicago Midway - Montego Bay Sangster Intl), can usually be booked for $334.

  • 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 $595). 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 Januar 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$341Average$446FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$630FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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