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Montego Bay

$165+ Cheap flights from Midway (MDW) to Montego Bay (MBJ)

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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap flight deals from Midway to Montego Bay

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Montego Bay (MBJ). 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 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$448
(Booking.com)

One-way from

$165
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$644

Good round-trip deal

$689 or less

Good one-way deal

$372 or less
Provider with most accurate pricing for Chicago Midway-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Montego Bay Sangster Intl flights.
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From Chicago Midway to Montego Bay Sangster Intl
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One-way flight from Chicago Midway to Montego Bay Sangster Intl
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Highest demand for flights based on searches. 2% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 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 Chicago Midway to Montego Bay Sangster Intl.
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Price to beat on a one-way flight from Chicago Midway to Montego Bay Sangster Intl.
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Find flight deals from Midway to Montego Bay

Cheapest flights from Midway to Montego Bay
Explore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 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 5/274:46 pmMDW - MBJ
1 stop15h 04mFrontier
Tue 6/39:08 amMBJ - MDW
1 stop13h 36mFrontier
Deal found 4/29$448
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.
Sun 5/116:00 amMDW - MBJ
1 stop9h 30mDelta
Wed 5/141:02 pmMBJ - MDW
1 stop8h 26mDelta
Deal found 4/29$449
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/59:05 amMDW - MBJ
Nonstop4h 00mSouthwest
Tue 7/82:20 pmMBJ - MDW
Nonstop4h 10mSouthwest
Deal found 4/29$473
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.
Fri 6/69:12 pmMDW - MBJ
2 stops13h 50mMultiple Airlines
Tue 6/102:02 pmMBJ - MDW
1 stop22h 53mMultiple Airlines
Deal found 4/29$487
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/107:21 pmMDW - MBJ
3 stops23h 05mWestJet
Tue 7/1512:45 pmMBJ - MDW
3 stops28h 54mWestJet
Deal found 4/29$807

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to Montego Bay 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 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.

Fly from

Midway

Fly to

Montego Bay

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 5/29

9:50 am-7:50 am

1 stop22h 00m

Montego Bay Sangster Intl

Sun 6/1

9:38 am-9:32 pm

1 stop11h 54m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 5/7

6:00 am-11:37 am

1 stop5h 37m

Montego Bay Sangster Intl

Wed 5/14

1:02 pm-9:28 pm

1 stop8h 26m

$449

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/24

9:40 am-1:40 pm

Nonstop4h 00m

Montego Bay Sangster Intl

Thu 5/29

12:00 pm-10:00 pm

1 stop10h 00m

$465

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/24

9:40 am-11:42 am

1 stop26h 02m

Montego Bay Sangster Intl

Thu 5/29

12:07 pm-7:14 pm

2 stops31h 07m

$467

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 7/10

7:21 pm-6:26 pm

3 stops23h 05m

Montego Bay Sangster Intl

Tue 7/15

12:45 pm-5:39 pm

3 stops28h 54m

$807

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 7/7

9:12 pm-11:02 am

2 stops13h 50m

$165

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 5/28

6:40 am-1:51 pm

1 stop7h 11m

$191

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 7/13

9:00 am-1:00 pm

Nonstop4h 00m

$203

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/1

6:00 am-3:25 pm

1 stop9h 25m

$208

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 6/18

12:44 pm-11:42 am

2 stops22h 58m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 11 results
1
2

Compare providers for flights from Midway to Montego Bay

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 Midway to Montego Bay in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 Chicago Midway Airport-Montego Bay flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Montego Bay flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Montego Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Montego Bay 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 Chicago Midway Airport-Montego Bay 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 Midway to Montego Bay

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $403). Flying from Chicago Midway Airport to Montego Bay in July is currently the most expensive (average of $569). 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.

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

Find hourly flight availability from Midway to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 30, 2025.

It’s optimal to fly from Chicago Midway Airport to Montego Bay at noon. By choosing this option you can save up to 44% on the cost of your flight, compared to a flight in the morning.

Rainfall in Montego Bay by month

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

In terms of precipitation, rainfall in Montego Bay ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Montego Bay when rainfall is around 1.6 in.

Temperature in Montego Bay by month

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

If weather is an important factor for your trip to Montego Bay, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Montego Bay

Get insights into the airlines that provide service to Montego Bay. 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 Montego Bay. Reviews last updated April 30, 2025.
To help decide which airline to fly from Chicago to Montego Bay, see what other customers have to say about Southwest, Delta and WestJet. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

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

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

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
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

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

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

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
3,287 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

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

    Montego Bay Sangster Intl (MBJ), located 2.3 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Montego Bay. 2 airlines have flights to Sangster Intl from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Montego Bay Sangster Intl should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

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

    Flying on Frontier is currently your cheapest option to Montego Bay, with prices starting at $448. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $449 and $473, respectively. Frontier is currently priced 40% below the average price you’ll pay for this route.

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

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Montego Bay are Frontier ($193), Southwest ($203), and Delta ($208).

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

    The cheapest flight price from Chicago Midway Airport to Montego Bay is $285. On average you can expect to pay $582. The most popular route, (Chicago Midway - Montego Bay Sangster Intl), can usually be booked for $422.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Montego Bay 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 Chicago Midway Airport to Montego Bay?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $403). Flying from Chicago Midway Airport to Montego Bay in July is currently the most expensive (average of $569). 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
Whitehouse
Lucea

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Alternative routes for Midway to Montego Bay

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

Top 2 airlines flying from Midway to Montego Bay

Discover the top 2 airlines that operate flights from Midway to Montego Bay. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$452Average$821FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$748FlexibilityNo cancel feeOn-time63%

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