$164 Cheap Flights from Chicago (MDW) to Montego Bay (MBJ)

View $164 flight on Mon, Aug 4, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)

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Cheap Flights from Chicago to Montego Bay (MDW-MBJ)

Prices were available within the past 7 days and start at $164 for one-way flights and $385 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Sep 8 - Fri, Sep 12
MDW
Chicago
MBJ
Montego Bay
$385 Roundtrip, just found
$385
Roundtrip
just found
Select Delta flight, departing Mon, Sep 8 from Chicago to Montego Bay, returning Fri, Sep 12, priced at $385 just found
Delta
Tue, Aug 12 - Thu, Sep 4
MDW
Chicago
MBJ
Montego Bay
$388 Roundtrip, found 1 hour ago
$388
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 12 from Chicago to Montego Bay, returning Thu, Sep 4, priced at $388 found 1 hour ago
Southwest Airlines
Wed, Oct 8 - Tue, Oct 14
MDW
Chicago
MBJ
Montego Bay
$389 Roundtrip, found 1 hour ago
$389
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Oct 8 from Chicago to Montego Bay, returning Tue, Oct 14, priced at $389 found 1 hour ago
Southwest Airlines
Mon, Sep 15 - Fri, Sep 19
MDW
Chicago
MBJ
Montego Bay
$392 Roundtrip, found 1 day ago
$392
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Montego Bay, returning Fri, Sep 19, priced at $392 found 1 day ago
Frontier Airlines
Fri, Jul 25 - Tue, Aug 12
MDW
Chicago
MBJ
Montego Bay
$393 Roundtrip, found 5 days ago
$393
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jul 25 from Chicago to Montego Bay, returning Tue, Aug 12, priced at $393 found 5 days ago
Southwest Airlines
Mon, Sep 8 - Fri, Sep 12
MDW
Chicago
MBJ
Montego Bay
$394 Roundtrip, just found
$394
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Sep 8 from Chicago to Montego Bay, returning Fri, Sep 12, priced at $394 just found
Southwest Airlines
Wed, Oct 1 - Wed, Oct 8
MDW
Chicago
MBJ
Montego Bay
$394 Roundtrip, found 1 hour ago
$394
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Chicago to Montego Bay, returning Wed, Oct 8, priced at $394 found 1 hour ago
Southwest Airlines
Tue, Aug 12 - Thu, Sep 4
MDW
Chicago
MBJ
Montego Bay
$395 Roundtrip, found 1 hour ago
$395
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to Montego Bay, returning Thu, Sep 4, priced at $395 found 1 hour ago
Southwest Airlines
Mon, Oct 13 - Sat, Oct 18
MDW
Chicago
MBJ
Montego Bay
$396 Roundtrip, found 5 days ago
$396
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Oct 13 from Chicago to Montego Bay, returning Sat, Oct 18, priced at $396 found 5 days ago
Southwest Airlines
Wed, Oct 1 - Wed, Oct 8
MDW
Chicago
MBJ
Montego Bay
$398 Roundtrip, found 1 hour ago
$398
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Chicago to Montego Bay, returning Wed, Oct 8, priced at $398 found 1 hour ago

Find the cheapest month to fly from Chicago (MDW) to Montego Bay (MBJ)

October is typically the cheapest month to fly

From $268 - $878 per traveler.

Graph displaying average flight prices per month

Alternative airports near Montego Bay

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Sir Donald Sangster Intl. MBJ. Cheapest and Closest option available. Average driving time to city center is 4 minutes. Flights from $439
MBJ
Sir Donald Sangster Intl.
CheapestClosest
Average driving time to city center4 min
Flights from $439
0
Flights from Chicago (MDW) to Montego Bay (MBJ)
Origin airport
Midway Intl.
Destination airport
Sir Donald Sangster Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$384
Distance
1709 mi

Chicago to Montego Bay Flights

The cheapest times to fly from Chicago to Montego Bay

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Montego Bay are during the month of September. You can find some of the cheapest flights from Chicago to Montego Bay with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Montego Bay

Sunday is one of the best days to book for cheap flights from Chicago to Montego Bay: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Montego Bay

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Montego Bay in 2025. You can also book with separate airlines for your outbound and return journeys, from $164 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Montego Bay flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Montego Bay airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ) cost?
You can score cheap return tickets from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ) starting at $395. Snag a seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on July 11 2025 and touching down at MBJ. The price was last updated on July 1 2025 and has not changed since.
What is the cheapest month to fly from MDW to MBJ?
Snag a low fare by booking your nonstop flight from MDW to MBJ in July. You can find a one-way Southwest Airlines flight for $164 leaving on July 29 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on July 1 2025 and remains unchanged.
Which airlines fly direct from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
When setting off from Midway Intl. Airport (MDW), you can board a direct flight to Sir Donald Sangster Intl. Airport (MBJ) with Southwest Airlines.
What is the cheapest airline that flies from MDW to MBJ?
Take off from MDW to MBJ with Southwest Airlines. This carrier currently has the cheapest one-way ticket on this route, starting at $164. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on July 29 2025. Prices were last updated on July 1 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
On average, you can take your pick of 1 direct flights departing from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ) every week. If you don't see one that works for your schedule, think about hopping on a flight that includes a layover. Filter your search results on Expedia to include one or more stops and opt for the best alternative.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
Flights between MDW and MBJ tend to be busiest at 8 AM. If you want a more relaxed trip and possibly cheaper prices, look for a departure that's outside typical rush times.
What day of the week has the most flights from MDW to MBJ?
Depart on a Saturday if you're searching for the largest selection of flights from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ).
What is the earliest flight from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
Take the earliest flight at around 8:25AM UTC-6, leaving from Midway Intl. Airport (MDW). You'll be traveling for about 3h 55m, touching down at Sir Donald Sangster Intl. Airport (MBJ) at approximately 1:20PM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
It takes roughly 3 hours and 55 minutes to travel the 1,700 mi from MDW to MBJ.
What is the best time to fly from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
Choose a flight from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ) that takes off before 3 PM to reduce the risk of delays and cancellations. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Montego Bay from Midway Intl. Airport (MDW)?
Check out your flight options from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ). This is the only Montego Bay airport you can touch down at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ) last-minute?
Holding off until just before your departure to book a ticket from MDW to MBJ generally means paying more. While you may come across some last-minute discounts, there's no guarantee. Allow some flexibility in your schedule for a better chance of getting a bargain.
Is it cheaper to book a MDW to MBJ flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to MBJ flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one place takes the hassle out of travel planning. Just secure your flights and choose from our wide range of hotels, then tailor your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
Typically, it's possible to reschedule or cancel your MDW to MBJ flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

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