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Montego Bay

$161+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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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 August 14, 2025.

Round-trip from

$392
(FlightHub)

One-way from

$161
(Priceline)

Popular in

October

Cheapest in

July

Average price

$845
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. 4% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 14, 2025.

This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1310:51 amMDW - MBJ
2 stops25h 50mFrontier
Sat 9/202:05 pmMBJ - MDW
1 stop9h 12mFrontier
Deal found 8/13$392
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:20 amMDW - MBJ
1 stop6h 25mFrontier
Sat 9/202:05 pmMBJ - MDW
1 stop9h 12mFrontier
Deal found 8/13$400
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:26 pmMDW - MBJ
1 stop17h 10mFrontier
Mon 10/203:51 pmMBJ - MDW
1 stop21h 47mFrontier
Deal found 8/14$403
This Southwest deal was found by Cheapflights users on 8/12. 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.
Tue 10/75:25 amMDW - MBJ
1 stop6h 35mSouthwest
Tue 10/72:25 pmMBJ - MDW
1 stop8h 10mSouthwest
Deal found 8/12$405
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Wed 10/298:00 amMDW - MBJ
1 stop23h 53mFrontier
Sun 11/210:13 amMBJ - MDW
1 stop14h 12mFrontier
Deal found 8/12$406
This Frontier deal was found by Cheapflights users on 8/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/27:23 pmMDW - MBJ
1 stop12h 30mFrontier
Thu 11/610:13 amMBJ - MDW
1 stop9h 05mFrontier
Deal found 8/12$408
This Priceline deal was found by Cheapflights users on 8/11. 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.
Sun 9/146:20 amMDW - MBJ
1 stop6h 21mFrontier
Sat 9/202:05 pmMBJ - MDW
1 stop9h 12mFrontier
Deal found 8/11$409
This Southwest deal was found by Cheapflights users on 8/14. 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.
Sat 10/186:00 amMDW - MBJ
1 stop8h 00mSouthwest
Thu 10/2312:50 pmMBJ - MDW
2 stops7h 50mSouthwest
Deal found 8/14$410
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:15 amMDW - MBJ
1 stop6h 30mFrontier
Fri 9/192:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 8/13$413
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3111:03 amMDW - MBJ
1 stop20h 52mFrontier
Sat 9/62:05 pmMBJ - MDW
2 stops22h 39mFrontier
Deal found 8/14$415
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 10/306:20 amMDW - MBJ
1 stop8h 55mFrontier
Sun 11/24:30 pmMBJ - MDW
1 stop27h 09mFrontier
Deal found 8/13$417
This Frontier deal was found by Cheapflights users on 8/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:20 amMDW - MBJ
1 stop6h 25mFrontier
Fri 10/32:12 pmMBJ - MDW
2 stops19h 39mFrontier
Deal found 8/13$420

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 August 14, 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

Fri 11/7

7:23 pm-8:53 am

1 stop12h 30m

Montego Bay Sangster Intl

Mon 11/10

10:13 am-6:18 pm

1 stop9h 05m

$392

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/13

6:20 am-2:36 pm

1 stop8h 16m

Montego Bay Sangster Intl

Thu 10/16

3:51 pm-11:25 pm

1 stop7h 34m

$392

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/13

10:51 am-12:41 pm

2 stops25h 50m

Montego Bay Sangster Intl

Sat 9/20

2:05 pm-11:17 pm

1 stop9h 12m

$392

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/14

6:20 am-12:41 pm

1 stop6h 21m

Montego Bay Sangster Intl

Sat 9/20

2:05 pm-11:17 pm

1 stop9h 12m

$400

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 9/12

6:20 am-12:45 pm

1 stop6h 25m

Montego Bay Sangster Intl

Sat 9/20

2:05 pm-11:17 pm

1 stop9h 12m

$400

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/20

6:20 am-2:36 pm

1 stop8h 16m

Montego Bay Sangster Intl

Sat 10/25

4:01 pm-11:25 pm

1 stop7h 24m

$400

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 10/29

8:00 am-7:53 am

1 stop23h 53m

Montego Bay Sangster Intl

Mon 11/3

10:13 am-6:18 pm

1 stop9h 05m

$403

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 10/16

9:26 pm-2:36 pm

1 stop17h 10m

Montego Bay Sangster Intl

Mon 10/20

3:51 pm-1:38 pm

1 stop21h 47m

$403

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 10/7

5:25 am-12:00 pm

1 stop6h 35m

Montego Bay Sangster Intl

Tue 10/7

2:25 pm-10:35 pm

1 stop8h 10m

$405

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 10/29

8:00 am-7:53 am

1 stop23h 53m

Montego Bay Sangster Intl

Sun 11/2

10:13 am-11:25 pm

1 stop14h 12m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 21 results
1
2
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 August 8, 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 $561). 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 August 14, 2025.

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.

What’s the top layover airport for flights from Chicago Midway Airport to Montego Bay?

Share of 1-stop round-trip flights from Chicago Midway Airport to Montego Bay chosen by Cheapflights users in the past 12 months, using the same layover each way.

Baltimore (BWI) – chosen by Cheapflights users on 33% of 1-stop itineraries from Chicago Midway Airport to Montego Bay on Cheapflights.

What’s the cheapest layover airport for flights from Chicago Midway Airport to Montego Bay?

Average round-trip fare for 1-stop flights from Chicago Midway Airport to Montego Bay, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $370.

What’s the fastest layover option from Chicago Midway Airport to Montego Bay?

Shortest average travel time for 1-stop one-way flights from Chicago Midway Airport to Montego Bay, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 6h 05m.

Which airport typically offers the quickest layover for flights from Chicago Midway Airport to Montego Bay?

Average layover duration for 1-stop one-way flights from Chicago Midway Airport to Montego Bay, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 1h 20m.

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 August 14, 2025.
Read reviews from past customers who have flown Southwest and Delta 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.
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 Delta is currently your cheapest option to Montego Bay, with prices starting at $458. Another option worth looking into is Southwest, starting at $555 round trip. Delta is currently priced 36% below the average price you’ll pay for this route.

  • 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 $561). 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
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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$458Average$789FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$555Average$724FlexibilityNo cancel feeOn-time63%

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