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$207+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$355
(Booking.com)

One-way from

$207
(Trip.com)

Popular in

August

Cheapest in

September

Average price

$608

Good round-trip deal

$460 or less

Good one-way deal

$312 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. 9% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Booking.com deal was found by Cheapflights users on 7/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/149:05 amMBJ - MDW
1 stop14h 12mFrontier
Mon 8/186:20 amMDW - MBJ
1 stop8h 20mFrontier
Deal found 7/27$355
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1510:52 amMBJ - MDW
1 stop7h 51mMultiple Airlines
Thu 9/251:49 pmMDW - MBJ
1 stop19h 58mMultiple Airlines
Deal found 7/26$367
This Southwest deal was found by Cheapflights users on 7/26. 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.
Sun 11/93:25 pmMBJ - MDW
2 stops10h 25mSouthwest
Wed 11/196:40 amMDW - MBJ
1 stop6h 45mSouthwest
Deal found 7/26$537
This WestJet deal was found by Cheapflights users on 7/28. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:45 pmMBJ - MDW
2 stops24h 18mWestJet
Thu 9/1812:43 pmMDW - MBJ
2 stops20h 43mWestJet
Deal found 7/28$1,267

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 July 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

Thu 8/14

9:05 am-11:17 pm

1 stop14h 12m

Chicago Midway

Mon 8/18

6:20 am-2:40 pm

1 stop8h 20m

$355

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 9/15

10:52 am-6:43 pm

1 stop7h 51m

Chicago Midway

Thu 9/25

1:49 pm-9:47 am

1 stop19h 58m

$367

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 11/9

3:25 pm-12:50 am

2 stops10h 25m

Chicago Midway

Wed 11/19

6:40 am-2:25 pm

1 stop6h 45m

$537

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/11

12:45 pm-1:03 pm

2 stops24h 18m

Chicago Midway

Thu 9/18

12:43 pm-9:26 am

2 stops20h 43m

$1,267

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 10/18

9:13 am-11:09 pm

1 stop13h 56m

$207

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 9/17

2:35 pm-9:36 pm

1 stop7h 01m

$215

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/16

12:50 pm-7:20 pm

1 stop6h 30m

$220

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 10/29

12:10 pm-7:20 am

2 stops19h 10m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 July 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.

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 July 29, 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).

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 July 29, 2025.
See what other customers who have flown with Southwest, Delta, and WestJet 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
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
2,973 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $355 on this airline. Additional options worth looking into are Southwest and WestJet, starting at $537 and $1,267 round-trip. Users have found that Frontier is 39% 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 $207. Users have also found prices from $215 and $220 on Delta and Southwest, 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 $236. On average you can expect to pay $586. The most popular route, (Montego Bay Sangster Intl - Chicago Midway), can usually be booked for $367.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%

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