$200 Cheap Flights from Chicago (MDW) to Montego Bay (MBJ)

View $200 flight on Mon, May 26, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $200 for one-way flights and $391 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Sep 16 - Thu, Sep 25
MDW
Chicago
MBJ
Montego Bay
$391 Roundtrip, found 6 days ago
$391
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 16 from Chicago to Montego Bay, returning Thu, Sep 25, priced at $391 found 6 days ago
Delta
Tue, Sep 16 - Thu, Sep 25
MDW
Chicago
MBJ
Montego Bay
$436 Roundtrip, found 6 days ago
$436
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 16 from Chicago to Montego Bay, returning Thu, Sep 25, priced at $436 found 6 days ago
Frontier Airlines
Mon, Jun 2 - Fri, Jun 6
MDW
Chicago
MBJ
Montego Bay
$447 Roundtrip, found 1 hour ago
$447
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Jun 2 from Chicago to Montego Bay, returning Fri, Jun 6, priced at $447 found 1 hour ago
Southwest Airlines
Tue, May 6 - Fri, May 9
MDW
Chicago
MBJ
Montego Bay
$449 Roundtrip, found 14 hours ago
$449
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Tue, May 6 from Chicago to Montego Bay, returning Fri, May 9, priced at $449 found 14 hours ago
Delta
Wed, May 7 - Thu, May 8
MDW
Chicago
MBJ
Montego Bay
$452 Roundtrip, found 22 hours ago
$452
Roundtrip
found 22 hours ago
Select Delta flight, departing Wed, May 7 from Chicago to Montego Bay, returning Thu, May 8, priced at $452 found 22 hours ago
Southwest Airlines
Sun, May 11 - Fri, May 16
MDW
Chicago
MBJ
Montego Bay
$453 Roundtrip, found 5 hours ago
$453
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sun, May 11 from Chicago to Montego Bay, returning Fri, May 16, priced at $453 found 5 hours ago
Frontier Airlines
Thu, May 8 - Thu, May 15
MDW
Chicago
MBJ
Montego Bay
$455 Roundtrip, found 1 hour ago
$455
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to Montego Bay, returning Thu, May 15, priced at $455 found 1 hour ago
Southwest Airlines
Sun, Sep 28 - Fri, Oct 3
MDW
Chicago
MBJ
Montego Bay
$457 Roundtrip, found 2 days ago
$457
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Sep 28 from Chicago to Montego Bay, returning Fri, Oct 3, priced at $457 found 2 days ago
Southwest Airlines
Mon, May 12 - Thu, May 15
MDW
Chicago
MBJ
Montego Bay
$457 Roundtrip, found 1 day ago
$457
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, May 12 from Chicago to Montego Bay, returning Thu, May 15, priced at $457 found 1 day ago
Southwest Airlines
Sun, May 11 - Fri, May 16
MDW
Chicago
MBJ
Montego Bay
$459 Roundtrip, found 5 hours ago
$459
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sun, May 11 from Chicago to Montego Bay, returning Fri, May 16, priced at $459 found 5 hours ago

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 $476. 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 May 10 2025 and touching down at MBJ. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from MDW to MBJ?
The cheapest flights from MDW to MBJ are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 $217. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on May 17 2025. Prices were last updated on April 24 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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