$220 Cheap Flights from Montego Bay (MBJ) to Chicago (MDW)

View $220 flight on Fri, Oct 3, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $220 for one-way flights and $339 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Sep 13 - Sat, Sep 27
MBJ
Montego Bay
MDW
Chicago
$339 Roundtrip, found 6 days ago
$339
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Montego Bay to Chicago, returning Sat, Sep 27, priced at $339 found 6 days ago
Frontier Airlines
Sat, Sep 13 - Mon, Sep 29
MBJ
Montego Bay
MDW
Chicago
$341 Roundtrip, found 6 days ago
$341
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Montego Bay to Chicago, returning Mon, Sep 29, priced at $341 found 6 days ago
Frontier Airlines
Fri, Sep 26 - Mon, Sep 29
MBJ
Montego Bay
MDW
Chicago
$343 Roundtrip, found 1 day ago
$343
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Sep 26 from Montego Bay to Chicago, returning Mon, Sep 29, priced at $343 found 1 day ago
Frontier Airlines
Sat, Aug 30 - Sat, Sep 6
MBJ
Montego Bay
MDW
Chicago
$344 Roundtrip, found 5 days ago
$344
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Montego Bay to Chicago, returning Sat, Sep 6, priced at $344 found 5 days ago
Frontier Airlines
Sat, Aug 23 - Sat, Sep 6
MBJ
Montego Bay
MDW
Chicago
$346 Roundtrip, found 23 hours ago
$346
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Aug 23 from Montego Bay to Chicago, returning Sat, Sep 6, priced at $346 found 23 hours ago
Delta
Fri, Oct 3 - Tue, Oct 7
MBJ
Montego Bay
MDW
Chicago
$348 Roundtrip, just found
$348
Roundtrip
just found
Select Delta flight, departing Fri, Oct 3 from Montego Bay to Chicago, returning Tue, Oct 7, priced at $348 just found
Southwest Airlines
Thu, Oct 16 - Mon, Oct 27
MBJ
Montego Bay
MDW
Chicago
$348 Roundtrip, found 3 days ago
$348
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 16 from Montego Bay to Chicago, returning Mon, Oct 27, priced at $348 found 3 days ago
Frontier Airlines
Sat, Sep 27 - Mon, Sep 29
MBJ
Montego Bay
MDW
Chicago
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 27 from Montego Bay to Chicago, returning Mon, Sep 29, priced at $349 found 1 day ago
Frontier Airlines
Sat, Sep 13 - Wed, Oct 1
MBJ
Montego Bay
MDW
Chicago
$351 Roundtrip, found 6 days ago
$351
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Montego Bay to Chicago, returning Wed, Oct 1, priced at $351 found 6 days ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
MBJ
Montego Bay
MDW
Chicago
$352 Roundtrip, found 2 days ago
$352
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Montego Bay to Chicago, returning Sat, Sep 13, priced at $352 found 2 days ago

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

November is typically the cheapest month to fly

From $241 - $888 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $364
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $364
Flights from Montego Bay (MBJ) to Chicago (MDW)
Origin airport
Sir Donald Sangster Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$339
Distance
1709 mi
Average flight time
5 hours 10 mins

Montego Bay to Chicago Flights

The cheapest times to fly from Montego Bay to Chicago

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 Montego Bay to Chicago are during the month of September. You can find some of the cheapest flights from Montego Bay to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Montego Bay to Chicago: 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 Montego Bay to Chicago

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 Montego Bay to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $220 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 Montego Bay to Chicago 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 Montego Bay to Chicago 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 Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from MBJ to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MBJ to MDW?
The cheapest flights from MBJ to MDW 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 Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW)?
Catch a direct flight with Southwest Airlines and head straight from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from MBJ to MDW?
Take off from MBJ to MDW with Southwest Airlines. This airline currently offers the cheapest one-way fare for this route, starting at $345. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MBJ on July 29 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW)?
On average, there are 1 direct flights taking off from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW) every week. If you don't see one that fits your schedule, think about a flight with a layover. Filter your search results on Expedia to include one stop or more and select the best alternative.
What are the most popular departure times for flights from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW)?
More people fly between MBJ and MDW at 2 PM than at any other time. Looking to skip the crowds? Consider flying outside peak hours and you're likely to save on your fare as well.
What day of the week has the most flights from MBJ to MDW?
Saturday offers the most flights from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW). Consider taking off on this day and you'll have a greater chance of finding a departure that fits your plans.
What is the earliest flight from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW)?
Sir Donald Sangster Intl. Airport (MBJ)'s first flight to Midway Intl. Airport (MDW) departs at approximately 2:10PM UTC-5. With a total travel time of 4h 15m, you'll arrive at around 5:25PM UTC-6.
How long does it take to fly from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW)?
Flights from MBJ to MDW have an average travel time of 4 hours and 15 minutes. The distance between the two is 1,700 mi.
What is the best time to fly from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW)?
Opt for a flight from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**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 Chicago from Sir Donald Sangster Intl. Airport (MBJ)?
If you're catching a direct flight from Sir Donald Sangster Intl. Airport (MBJ) to Chicago, you'll come into land at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a ticket from MBJ to MDW generally means paying more. Although you may find some last-minute offers, they're not always guaranteed. Keep your travel plans flexible to maximize your chances of scoring a bargain.
Is it cheaper to book a MBJ to MDW flight and hotel package?
You can save money by securing a MBJ to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've chosen your preferred flights and accommodations, consider other add-ons like activities, car rentals and tours.
Can I cancel or change the date of my flight from Sir Donald Sangster Intl. Airport (MBJ) to Midway Intl. Airport (MDW)?
If you booked your MBJ to MDW flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

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*Available to One Key members.