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$220+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$386
(Booking.com)

One-way from

$220
(Southwest)

Popular in

August

Cheapest in

March

Average price

$657

Good one-way deal

$262 or less
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 ($119 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 16, 2025.

This Booking.com deal was found by Cheapflights users on 6/15. 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.
Fri 8/19:05 amMBJ - MDW
1 stop14h 12mFrontier
Thu 8/72:55 pmMDW - MBJ
1 stop17h 00mFrontier
Deal found 6/15$386
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Fri 8/13:53 pmMBJ - MDW
1 stop7h 24mMultiple Airlines
Thu 8/79:12 pmMDW - MBJ
2 stops13h 53mMultiple Airlines
Deal found 6/15$543
This Southwest deal was found by Cheapflights users on 6/14. 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.
Wed 6/182:20 pmMBJ - MDW
Nonstop4h 10mSouthwest
Wed 6/256:15 amMDW - MBJ
1 stop8h 40mSouthwest
Deal found 6/14$584

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 June 16, 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

Fri 8/1

9:05 am-11:17 pm

1 stop14h 12m

Chicago Midway

Thu 8/7

2:55 pm-7:55 am

1 stop17h 00m

$386

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 8/1

3:53 pm-11:17 pm

1 stop7h 24m

Chicago Midway

Thu 8/7

9:12 pm-11:05 am

2 stops13h 53m

$543

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 8/1

12:45 pm-12:10 am

2 stops11h 25m

Chicago Midway

Thu 8/7

5:25 am-2:00 pm

2 stops8h 35m

$715

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/23

2:55 pm-9:15 pm

1 stop6h 20m

$220

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/13

2:30 pm-9:49 pm

1 stop7h 19m

$221

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 8/12

3:45 pm-10:40 am

1 stop18h 55m

$227

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 8/21

12:14 pm-8:42 am

2 stops20h 28m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

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 June 16, 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.

Weekly flight availability from Montego Bay to Chicago Midway Airport

Explore weekly flight availability from Montego Bay to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 16, 2025.

The most flights from MBJ to MDW are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 June 16, 2025.
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,296 reviews
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 1 outbound flight 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 $386 on this airline. An additional option worth looking into is Southwest, starting at $715. Users have found that Frontier is 36% 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 Southwest. According to our data, you can fly for as low as $220. Users have also found prices from $221 and $227 on Delta and Frontier, 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 $262. On average you can expect to pay $545. The most popular route, (Montego Bay Sangster Intl - Chicago Midway), can usually be booked for $394.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$509Average$608FlexibilityNo cancel feeOn-time63%

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