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$225+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$412
(Booking.com)

One-way from

$225
(Kiwi.com)

Popular in

August

Cheapest in

March

Average price

$608

Good round-trip deal

$532 or less

Good one-way deal

$287 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago Midway flights.
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From Montego Bay Sangster Intl to Chicago Midway
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One-way flight from Montego Bay Sangster Intl to Chicago Midway
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Highest demand for flights based on searches. 16% potential increase in price ($118 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Montego Bay Sangster Intl to Chicago Midway.
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Price to beat on a one-way flight from Montego Bay Sangster Intl to Chicago Midway.
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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 April 29, 2025.

This Booking.com deal was found by Cheapflights users on 4/29. 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.
Tue 6/39:08 amMBJ - MDW
1 stop13h 36mFrontier
Tue 6/105:36 pmMDW - MBJ
1 stop19h 01mFrontier
Deal found 4/29$412
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/3111:31 amMBJ - MDW
1 stop9h 42mDelta
Sun 6/86:00 amMDW - MBJ
1 stop9h 25mDelta
Deal found 4/29$462
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/39:08 amMBJ - MDW
1 stop13h 36mMultiple Airlines
Tue 6/105:36 pmMDW - MBJ
2 stops17h 26mMultiple Airlines
Deal found 4/29$476
This Southwest deal was found by Cheapflights users on 4/28. 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.
Mon 6/92:55 pmMBJ - MDW
2 stops10h 00mSouthwest
Thu 6/129:45 pmMDW - MBJ
2 stops15h 35mSouthwest
Deal found 4/28$717
This WestJet deal was found by Cheapflights users on 4/29. 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.
Sat 5/37:25 pmMBJ - MDW
2 stops26h 57mWestJet
Thu 7/3112:38 pmMDW - MBJ
2 stops20h 49mWestJet
Deal found 4/29$2,046

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 April 29, 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

Tue 6/3

9:08 am-10:44 pm

1 stop13h 36m

Chicago Midway

Tue 6/10

5:36 pm-12:37 pm

1 stop19h 01m

$412

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/31

11:31 am-9:13 pm

1 stop9h 42m

Chicago Midway

Sun 6/8

6:00 am-3:25 pm

1 stop9h 25m

$462

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 6/3

9:08 am-10:44 pm

1 stop13h 36m

Chicago Midway

Tue 6/10

5:36 pm-11:02 am

2 stops17h 26m

$476

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 6/9

2:55 pm-12:55 am

2 stops10h 00m

Chicago Midway

Thu 6/12

9:45 pm-1:20 pm

2 stops15h 35m

$717

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/25

12:07 pm-8:17 pm

2 stops32h 10m

$225

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 5/30

9:05 am-10:14 pm

1 stop13h 09m

$246

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 7/9

2:20 pm-6:30 pm

Nonstop4h 10m

$249

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/20

1:15 pm-9:47 pm

1 stop8h 32m

$254

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 6/20

12:45 pm-5:12 pm

3 stops28h 27m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Montego Bay-Chicago Midway Airport flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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.

Cheapflights Insights

Everything you need to know about your flight from Montego Bay to Chicago Midway Airport

What is the cheapest time of day to fly from MBJ to MDW?

Find hourly flight availability from Montego Bay to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 29, 2025.

One of the essential ways to save on airfare from Montego Bay to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 26% on airfare.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 29, 2025.
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,823 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,284 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • What are the cheapest airlines flying from Montego Bay to Chicago Midway Airport round-trip?

    Our cheapest airline available from Montego Bay to Chicago Midway Airport is Frontier. Our recent data shows that you can find tickets from as low as $412 on this airline. Additional options worth looking into are Delta and Southwest, starting at $462 and $717 round-trip. Users have found that Frontier is 32% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Montego Bay to Chicago Midway Airport one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $246. Users have also found prices from $249 and $254 on Southwest and Delta, respectively.

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

    The cheapest flight price from Montego Bay to Chicago Midway Airport is $277. On average you can expect to pay $455. The most popular route, (Montego Bay Sangster Intl - Chicago Midway), can usually be booked for $455.

  • 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.

  • What is the cheapest month to book a flight from Montego Bay to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Montego Bay to Chicago Midway Airport (average of $160). Flying from Montego Bay to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$451Average$657FlexibilityNo cancel feeOn-time63%

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