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Montego Bay

$132+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
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 December 22, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$446
(Mytrip)

One-way from

$132
(Trip.com)

Popular in

December

Cheapest in

April

Average price

$1,001
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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High demand for flights, 0% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in December 2024
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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 December 22, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/2612:58 pmMDW - MBJ
2 stops23h 32mMultiple Airlines
Tue 12/3110:29 amMBJ - MDW
1 stop27h 55mMultiple Airlines
Deal found 12/19$685
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/308:25 amMDW - MBJ
1 stop23h 44mFrontier
Sun 1/51:29 pmMBJ - MDW
2 stops24h 37mFrontier
Deal found 12/20$719
This Southwest deal was found by Cheapflights users on 12/19. 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.
Fri 12/207:30 amMDW - MBJ
1 stop6h 35mSouthwest
Mon 12/231:45 pmMBJ - MDW
2 stops7h 50mSouthwest
Deal found 12/19$879
This Delta deal was found by Cheapflights users on 12/20. 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.
Tue 12/316:00 amMDW - MBJ
1 stop7h 48mDelta
Wed 1/2212:36 pmMBJ - MDW
1 stop10h 44mDelta
Deal found 12/20$947
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Mon 12/235:04 pmMDW - MBJ
3 stops25h 25mWestJet
Fri 12/272:55 pmMBJ - MDW
2 stops21h 13mWestJet
Deal found 12/21$2,203

Find flights from Midway to Montego Bay within your budget

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 December 22, 2024.

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Route

Depart

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Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/22

8:01 pm-10:34 am

1 stop13h 33m

Montego Bay Sangster Intl

Sun 1/26

11:48 am-9:32 pm

1 stop10h 44m

$446

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/4

6:00 am-12:47 pm

1 stop5h 47m

Montego Bay Sangster Intl

Tue 2/11

12:36 pm-10:20 pm

1 stop10h 44m

$479

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/5

5:25 am-11:05 am

1 stop5h 40m

Montego Bay Sangster Intl

Wed 4/9

2:55 pm-8:50 am

2 stops17h 55m

$564

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 1/13

11:33 am-11:15 am

2 stops22h 42m

Montego Bay Sangster Intl

Sat 1/18

2:20 pm-11:29 pm

1 stop10h 09m

$591

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/4

1:26 pm-1:48 pm

2 stops23h 22m

Montego Bay Sangster Intl

Tue 2/11

8:25 pm-12:42 pm

2 stops17h 17m

$884

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/25

7:30 am-10:38 am

1 stop26h 08m

$132

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/25

8:30 am-1:36 pm

2 stops28h 06m

$161

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 1/20

6:00 am-3:24 pm

1 stop8h 24m

$216

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/2

8:35 pm-12:45 pm

2 stops15h 10m

$222

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 3/17

10:24 am-12:48 pm

3 stops26h 24m

$385

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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

Travel insights for flights from Midway to Montego Bay

Get recent, data-driven insights about flights from Midway to Montego Bay including ideal travel times, pricing trends, and more.

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 December 22, 2024.

It’s optimal to fly from Chicago Midway Airport to Montego Bay at noon. By choosing this option you can save up to 40% 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 December 22, 2024.
To help decide which airline to fly from Chicago to Montego Bay, see what other customers have to say about Southwest, Delta and Frontier. 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
8.1
Very good
4,804 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,597 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.3
Good
2,812 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,472 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $446. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $479 and $564, respectively. Frontier is currently priced 38% 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 ($132), Delta ($216), and Southwest ($222).

  • 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.

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$458Average$790FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$723FlexibilityNo cancel feeOn-time63%
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