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Montego Bay

$138+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
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 septiembre 16, 2025.

Round-trip from

$380
(Kiwi.com)

One-way from

$138
(Trip.com)

Popular in

October

Cheapest in

July

Average price

$676
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. 5% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
jue. 10/306:20 amMDW - MBJ
1 stop8h 55mFrontier
jue. 11/64:30 pmMBJ - MDW
1 stop27h 09mFrontier
Deal found 9/15$380
This Delta deal was found by Cheapflights users on 9/15. 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.
lun. 9/296:00 amMDW - MBJ
1 stop7h 09mDelta
jue. 10/21:25 pmMBJ - MDW
1 stop8h 11mDelta
Deal found 9/15$385
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
dom. 12/76:00 amMDW - MBJ
1 stop8h 33mFrontier
sáb. 12/134:53 pmMBJ - MDW
1 stop7h 12mFrontier
Deal found 9/15$388
This Southwest deal was found by Cheapflights users on 9/14. 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.
vie. 10/38:45 pmMDW - MBJ
2 stops17h 15mSouthwest
mar. 10/71:00 pmMBJ - MDW
1 stop9h 35mSouthwest
Deal found 9/14$389
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/239:26 pmMDW - MBJ
1 stop17h 10mFrontier
dom. 10/263:51 pmMBJ - MDW
1 stop7h 55mFrontier
Deal found 9/13$390
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 11/186:00 amMDW - MBJ
1 stop5h 52mDelta
jue. 11/203:36 pmMBJ - MDW
1 stop8h 56mDelta
Deal found 9/15$391
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
vie. 12/126:00 amMDW - MBJ
1 stop8h 33mFrontier
lun. 12/154:53 pmMBJ - MDW
1 stop7h 12mFrontier
Deal found 9/14$392
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb. 10/116:15 amMDW - MBJ
1 stop8h 31mFrontier
vie. 10/173:51 pmMBJ - MDW
1 stop7h 55mFrontier
Deal found 9/15$393
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/195:35 amMDW - MBJ
2 stops8h 20mSouthwest
mar. 11/251:50 pmMBJ - MDW
2 stops10h 15mSouthwest
Deal found 9/13$395
This Frontier deal was found by Cheapflights users on 9/15. 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.
dom. 11/96:15 amMDW - MBJ
1 stop8h 00mFrontier
dom. 11/164:30 pmMBJ - MDW
2 stops17h 02mFrontier
Deal found 9/15$398
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 10/286:00 amMDW - MBJ
1 stop6h 07mDelta
jue. 11/61:48 pmMBJ - MDW
2 stops19h 52mDelta
Deal found 9/15$399
This Frontier deal was found by Cheapflights users on 9/16. 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.
sáb. 10/186:15 amMDW - MBJ
1 stop8h 31mFrontier
jue. 10/233:51 pmMBJ - MDW
1 stop7h 55mFrontier
Deal found 9/16$408

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 septiembre 16, 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

sáb. 10/18

6:25 am-1:35 pm

1 stop7h 10m

Montego Bay Sangster Intl

mar. 10/21

1:00 pm-12:05 am

2 stops11h 05m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 10/3

8:45 pm-2:00 pm

2 stops17h 15m

Montego Bay Sangster Intl

mar. 10/7

1:00 pm-10:35 pm

1 stop9h 35m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 11/17

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

vie. 11/21

5:59 pm-11:32 pm

1 stop6h 33m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 11/16

6:00 am-4:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

mié. 11/19

5:59 pm-11:32 pm

1 stop6h 33m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 11/19

6:40 am-2:25 pm

1 stop6h 45m

Montego Bay Sangster Intl

mar. 11/25

1:50 pm-9:55 pm

1 stop9h 05m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 12/8

6:00 am-4:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

mar. 12/16

5:59 pm-11:32 pm

1 stop6h 33m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 11/11

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

vie. 11/21

5:59 pm-11:32 pm

1 stop6h 33m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 11/18

6:00 am-12:52 pm

1 stop5h 52m

Montego Bay Sangster Intl

jue. 11/20

3:36 pm-11:32 pm

1 stop8h 56m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 11/16

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

vie. 11/21

5:59 pm-9:51 am

1 stop16h 52m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 11/17

6:00 am-4:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

mar. 11/25

5:59 pm-8:52 am

2 stops15h 53m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 21 results
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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 $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 septiembre 16, 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.

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 septiembre 16, 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.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago Midway Airport to Montego Bay?

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Montego Bay in about 7h 10m. The time it takes to get you to your destination can typically vary by up to 01m. Chicago Midway Airport and Montego Bay are separated by a distance of 1709 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $370. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $448 and $549, respectively. Frontier is currently priced 47% 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 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$446FlexibilityNo cancel feeOn-time62%
DeltaCheapest$448Average$645FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$726FlexibilityNo cancel feeOn-time63%

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