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$187+ Cheap flights from Montego Bay (MBJ) to Midway (MDW)

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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Montego Bay to Midway

Cheapest flights from Montego Bay to Midway
Explore the most affordable flight options available from Montego Bay to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Frontier deal was found by Cheapflights users on 12/10. 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.
Thu 12/253:47 pmMBJ - MDW
1 stop7h 25mFrontier
Wed 12/316:12 amMDW - MBJ
1 stop7h 17mFrontier
Deal found 12/10$322
This Delta deal was found by Cheapflights users on 12/10. 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 12/232:23 pmMBJ - MDW
1 stop8h 59mDelta
Sun 12/286:00 amMDW - MBJ
1 stop13h 41mDelta
Deal found 12/10$505
This Delta deal was found by Cheapflights users on 12/10. 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 12/218:00 amMBJ - MDW
1 stop15h 22mDelta
Sun 12/286:00 amMDW - MBJ
1 stop13h 41mDelta
Deal found 12/10$535
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/231:05 pmMBJ - MDW
2 stops34h 07mMultiple Airlines
Sun 12/286:00 amMDW - MBJ
1 stop7h 54mMultiple Airlines
Deal found 12/10$613
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Sun 12/211:05 pmMBJ - MDW
2 stops8h 59mMultiple Airlines
Sun 12/286:00 amMDW - MBJ
1 stop7h 54mMultiple Airlines
Deal found 12/10$661
This Delta deal was found by Cheapflights users on 12/10. 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.
Thu 12/258:00 amMBJ - MDW
2 stops10h 26mDelta
Wed 12/319:29 amMDW - MBJ
2 stops10h 12mDelta
Deal found 12/10$904
This Southwest deal was found by Cheapflights users on 12/10. 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.
Tue 12/231:50 pmMBJ - MDW
2 stops10h 15mSouthwest
Sun 12/281:50 pmMDW - MBJ
2 stops21h 10mSouthwest
Deal found 12/10$1,289

Find flight deals from Montego Bay to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Montego Bay (MBJ) to Midway (MDW). 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$322
(Frontier)

One-way from

$187
(Trip.com)

Popular in

February

Cheapest in

November

Average price

$441
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago Midway flights.
Search Deals
From Montego Bay Sangster Intl to Chicago Midway
Search Deals
One-way flight from Montego Bay Sangster Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montego Bay to Midway 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 December 12, 2025.
Use the filters below to find and compare flights from Montego Bay to Chicago Midway Airport that are best for you.

Fly from

Montego Bay

Fly to

Midway

Route

Depart

Return

Price

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 12/25

3:47 pm-10:12 pm

1 stop7h 25m

Chicago Midway

Wed 12/31

6:12 am-2:29 pm

1 stop7h 17m

$322

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 12/23

2:23 pm-10:22 pm

1 stop8h 59m

Chicago Midway

Sun 12/28

6:00 am-8:41 pm

1 stop13h 41m

$505

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 12/21

8:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Sun 12/28

6:00 am-8:41 pm

1 stop13h 41m

$535

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 12/23

1:05 pm-10:12 pm

2 stops34h 07m

Chicago Midway

Sun 12/28

6:00 am-2:54 pm

1 stop7h 54m

$613

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 12/21

1:05 pm-9:04 pm

2 stops8h 59m

Chicago Midway

Sun 12/28

6:00 am-2:54 pm

1 stop7h 54m

$661

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 12/25

8:00 am-5:26 pm

2 stops10h 26m

Chicago Midway

Wed 12/31

9:29 am-8:41 pm

2 stops10h 12m

$904

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 1/22

2:55 pm-12:46 pm

2 stops22h 51m

Chicago Midway

Mon 1/26

1:26 pm-7:23 pm

2 stops28h 57m

$1,104

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 1/25

1:25 pm-12:46 pm

2 stops24h 21m

Chicago Midway

Sun 2/1

9:33 am-1:49 pm

2 stops27h 16m

$1,129

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 12/23

1:50 pm-11:05 pm

2 stops10h 15m

Chicago Midway

Sun 12/28

1:50 pm-12:00 pm

2 stops21h 10m

$1,289

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 2/26

4:51 pm-11:25 pm

1 stop7h 34m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 18 results
1
2

Compare providers for flights from Montego Bay to Midway

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 Montego Bay to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 Montego Bay-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Montego Bay-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Montego Bay-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montego Bay-Chicago Midway Airport 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 Montego Bay-Chicago Midway Airport 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 Montego Bay to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Montego Bay 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 12, 2025.
See what other customers who have flown with Southwest from Montego Bay to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

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 Montego Bay to Midway. 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 from for flights from Montego Bay to Chicago Midway?

    Montego Bay Sangster Intl (MBJ), located 2.3 mi from the city center, is the airport you fly out of when you book flights from Montego Bay to Chicago Midway. 1 airline have flights from Sangster Intl to Chicago Midway on a regular basis. Booking flights from Montego Bay Sangster Intl to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    For as low as $322, Frontier can have you in Chicago Midway Airport from Montego Bay in 7h 25m. Airlines will cover 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 is the cheapest airline to fly from Montego Bay to Chicago Midway Airport round-trip?

    Our cheapest airline available from Montego Bay to Chicago Midway Airport is Southwest. Our recent data shows that you can find tickets from as low as $392 on this airline.

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

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

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

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

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

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

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Montego Bay to Midway

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

Top airline flying from Montego Bay to Midway

Discover the top airline that operate flights from Montego Bay to Midway. 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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