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$199+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Find 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 October 28, 2025.

This Booking.com deal was found by Cheapflights users on 10/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/304:30 pmMBJ - MDW
1 stop29h 15mFrontier
Sat 11/16:20 amMDW - MBJ
1 stop7h 55mFrontier
Deal found 10/26$500
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 10/3012:50 pmMBJ - MDW
2 stops7h 50mSouthwest
Sat 11/18:15 amMDW - MBJ
1 stop5h 45mSouthwest
Deal found 10/26$506
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:26 pmMBJ - MDW
1 stop7h 46mMultiple Airlines
Thu 12/183:10 pmMDW - MBJ
1 stop21h 47mMultiple Airlines
Deal found 10/27$520
This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/202:43 pmMBJ - MDW
1 stop9h 00mFrontier
Sun 11/236:05 amMDW - MBJ
1 stop8h 30mFrontier
Deal found 10/27$522
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Thu 10/301:55 pmMBJ - MDW
2 stops23h 13mMultiple Airlines
Sat 11/19:20 amMDW - MBJ
3 stops32h 45mMultiple Airlines
Deal found 10/26$1,653
This WestJet deal was found by Cheapflights users on 10/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:55 pmMBJ - MDW
2 stops23h 15mWestJet
Thu 12/189:59 amMDW - MBJ
2 stops32h 24mWestJet
Deal found 10/27$1,763
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/291:40 pmMBJ - MDW
2 stops23h 28mMultiple Airlines
Sat 11/13:00 pmMDW - MBJ
3 stops27h 05mMultiple Airlines
Deal found 10/27$2,079

Cheap 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$520
(Kiwi.com)

One-way from

$199
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$744
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. 3% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 28, 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 11/20

2:43 pm-10:43 pm

1 stop9h 00m

Chicago Midway

Sun 11/23

6:05 am-3:35 pm

1 stop8h 30m

$522

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 12/11

3:26 pm-10:12 pm

1 stop7h 46m

Chicago Midway

Thu 12/18

6:33 pm-1:57 pm

2 stops18h 24m

$607

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 3/30

4:06 pm-11:42 pm

1 stop7h 36m

Chicago Midway

Mon 4/6

2:00 pm-12:49 pm

2 stops22h 49m

$790

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 3/30

3:05 pm-12:45 am

1 stop9h 40m

Chicago Midway

Mon 4/6

6:30 am-2:05 pm

1 stop7h 35m

$828

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 12/11

2:55 pm-1:10 pm

2 stops23h 15m

Chicago Midway

Thu 12/18

9:59 am-7:23 pm

2 stops32h 24m

$1,763

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 1/22

4:45 pm-10:26 pm

1 stop6h 41m

$209

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/13

5:58 pm-11:47 pm

1 stop6h 49m

$209

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 11/25

3:36 pm-11:40 pm

1 stop9h 04m

$209

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 11/26

3:36 pm-11:40 pm

1 stop9h 04m

$209

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 2/5

12:38 pm-10:26 pm

1 stop10h 48m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 15 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 October.
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 October 28, 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
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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 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 $522, Frontier can have you in Chicago Midway Airport from Montego Bay in 9h. 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. Users have found that Southwest is 30% cheaper than the other options available to this destination.

  • 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
Merrillville
Lansing
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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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