Montego Bay

$109+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Jul 8 — Jul 151
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Cheapflights Tip: The best prices from Chicago Midway to Montego Bay Sangster Intl are usually found in July or November, booked 85 days in advance, depart on a Thursday or Friday and return on a Tuesday

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 July 3, 2025.

Round-trip from

$401
(Priceline)

One-way from

$109
(Priceline)

Popular in

December

Cheapest in

July

Average price

$620

Good round-trip deal

$549 or less
From Chicago Midway to Montego Bay Sangster Intl
One-way flight from Chicago Midway to Montego Bay Sangster Intl
Highest demand for flights based on searches. 3% potential increase in price ($23 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Chicago Midway to Montego Bay Sangster Intl.

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 July 3, 2025.

This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:10 amMDW - MBJ
1 stop6h 35mFrontier
Sat 9/272:05 pmMBJ - MDW
1 stop8h 28mFrontier
Deal found 7/1$401
This Delta deal was found by Cheapflights users on 7/1. 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 9/206:00 amMDW - MBJ
1 stop9h 34mDelta
Fri 9/262:35 pmMBJ - MDW
1 stop7h 01mDelta
Deal found 7/1$410
This Southwest deal was found by Cheapflights users on 7/1. 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 9/147:55 pmMDW - MBJ
2 stops17h 35mSouthwest
Thu 9/1812:45 pmMBJ - MDW
1 stop9h 40mSouthwest
Deal found 7/1$427
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Sat 7/269:12 pmMDW - MBJ
2 stops12h 41mMultiple Airlines
Sat 8/22:09 pmMBJ - MDW
1 stop24h 57mMultiple Airlines
Deal found 7/1$432

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 July 3, 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

Sat 9/20

6:10 am-12:45 pm

1 stop6h 35m

Montego Bay Sangster Intl

Sat 9/27

2:05 pm-10:33 pm

1 stop8h 28m

$401

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/20

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Thu 9/25

2:35 pm-9:36 pm

1 stop7h 01m

$410

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/14

7:55 pm-1:30 pm

2 stops17h 35m

Montego Bay Sangster Intl

Thu 9/18

12:45 pm-10:25 pm

1 stop9h 40m

$427

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/26

9:12 pm-9:53 am

2 stops12h 41m

Montego Bay Sangster Intl

Sat 8/2

2:09 pm-3:06 pm

1 stop24h 57m

$432

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 10/2

6:20 am-12:45 pm

1 stop6h 25m

$109

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 9/29

9:47 pm-11:10 am

2 stops13h 23m

$165

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/7

6:00 am-11:55 am

1 stop5h 55m

$169

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 11/4

5:35 am-2:55 pm

2 stops8h 20m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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

How far ahead should I book a flight from Chicago Midway Airport to Montego Bay?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Montego Bay. Price data was last updated on June 27, 2025.

The price you pay for your flight from Chicago Midway Airport to Montego Bay may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 3, 2025.

It’s optimal to fly from Chicago Midway Airport to Montego Bay at noon. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the morning.

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 July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier from Chicago Midway Airport to Montego Bay. 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.

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

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.

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

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.
8.0
Very good

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

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.

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

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 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. 3 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 $401. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $410 and $427, respectively. Frontier is currently priced 45% 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 ($109), Delta ($169), and Southwest ($207).

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

    The cheapest flight price from Chicago Midway Airport to Montego Bay is $455. On average you can expect to pay $712. The most popular route, (Chicago Midway - Montego Bay Sangster Intl), can usually be booked for $385.

  • 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.

Top 3 airlines flying from Midway to Montego Bay

Discover the top 3 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$338Average$436FlexibilityNo cancel feeOn-time62%
DeltaCheapest$452Average$790FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$555Average$726FlexibilityNo cancel feeOn-time63%

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