$169 Cheap Flights from Chicago (MDW) to Montego Bay (MBJ)

View $169 flight on Mon, Sep 8, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $169 for one-way flights and $373 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Sep 13 - Sat, Sep 20
MDW
Chicago
MBJ
Montego Bay
$373 Roundtrip, found 1 hour ago
$373
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Chicago to Montego Bay, returning Sat, Sep 20, priced at $373 found 1 hour ago
Frontier Airlines
Sat, Nov 1 - Sat, Nov 8
MDW
Chicago
MBJ
Montego Bay
$377 Roundtrip, found 1 day ago
$377
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 1 from Chicago to Montego Bay, returning Sat, Nov 8, priced at $377 found 1 day ago
Frontier Airlines
Sat, Oct 4 - Sat, Oct 11
MDW
Chicago
MBJ
Montego Bay
$379 Roundtrip, found 1 hour ago
$379
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 4 from Chicago to Montego Bay, returning Sat, Oct 11, priced at $379 found 1 hour ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
MDW
Chicago
MBJ
Montego Bay
$382 Roundtrip, found 4 hours ago
$382
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Chicago to Montego Bay, returning Sat, Sep 13, priced at $382 found 4 hours ago
Frontier Airlines
Sun, Sep 14 - Sat, Sep 20
MDW
Chicago
MBJ
Montego Bay
$383 Roundtrip, found 2 hours ago
$383
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Sep 14 from Chicago to Montego Bay, returning Sat, Sep 20, priced at $383 found 2 hours ago
Delta
Mon, Sep 8 - Thu, Sep 11
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 Thu, Sep 11, priced at $385 just found
Southwest Airlines
Sun, Oct 5 - Fri, Oct 10
MDW
Chicago
MBJ
Montego Bay
$385 Roundtrip, found 3 hours ago
$385
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sun, Oct 5 from Chicago to Montego Bay, returning Fri, Oct 10, priced at $385 found 3 hours ago
Southwest Airlines
Tue, Oct 21 - Tue, Oct 28
MDW
Chicago
MBJ
Montego Bay
$386 Roundtrip, found 4 days ago
$386
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Chicago to Montego Bay, returning Tue, Oct 28, priced at $386 found 4 days ago
Frontier Airlines
Sat, Nov 8 - Mon, Nov 10
MDW
Chicago
MBJ
Montego Bay
$388 Roundtrip, found 1 day ago
$388
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 8 from Chicago to Montego Bay, returning Mon, Nov 10, priced at $388 found 1 day ago
Delta
Tue, Oct 21 - Tue, Oct 28
MDW
Chicago
MBJ
Montego Bay
$389 Roundtrip, found 3 hours ago
$389
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Oct 21 from Chicago to Montego Bay, returning Tue, Oct 28, priced at $389 found 3 hours ago

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

November is typically the cheapest month to fly

From $286 - $931 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 $677
MBJ
Sir Donald Sangster Intl.
CheapestClosest
Average driving time to city center4 min
Flights from $677
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
$372
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 $169 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?
Secure a cheap one-way flight from $169 or cheap return flight from $373 from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
The cheapest month to fly from MDW to MBJ is September, when there's less demand. Off-peak months are typically when you'll find cheap fares for travel between these airports.
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 Midway Intl. Airport (MDW) to Sir Donald Sangster Intl. Airport (MBJ)?
To find the cheapest airline flying from MDW to MBJ, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
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.

Explore a world of travel with Expedia

*Available to One Key members.