CA $293 Cheap Flights from Montego Bay (MBJ) to Chicago (MDW)

View CA $293 flight on Tue, Oct. 21, 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 (MBJ) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $293 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

November is typically the cheapest month to fly

From CA $332 - CA $1,223 per traveller.

Graph displaying average flight prices per month

Flight from Montego Bay to Chicago (MBJ - MDW) route information
Origin airport
Sir Donald Sangster Intl.
Destination airport
Midway Intl.
Distance
2735 km

Montego Bay to Chicago Flights

The easy way to book your flights from Montego Bay to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Montego Bay whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Montego Bay to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Sir Donald Sangster Intl., MBJ to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Montego Bay to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Montego Bay currently is just rising to .  

Here are more money-saving tips: 

  • Fly in when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Montego Bay 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Frequently asked questions

How much is a flight from Sangster Intl. Airport to Midway Airport?
Based on fares offered within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between MBJ and Midway Airport start from . Book now to score the best price for your big adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MBJ to Chicago Airport?
Most flights can be cancelled online, but every air carrier has its own set of terms and conditions. If you do decide to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from MBJ to Midway Airport that have flexible change policies?
Plenty of airlines offer the option to move your flight without charging a fee. All you pay is the cost difference between flights. When searching for MBJ to Chicago Airport flights, you'll find a "No change fees" box for you to pick.
How many hours is the flight from MBJ to MDW?
Consider bringing your own on-board entertainment, as it takes about 5 hours and 39 minutes to arrive at Midway Airport from Sir Donald Sangster Intl. Airport (MBJ). A good pair of noise-cancelling earphones will also be useful.
How far is the flight from Sir Donald Sangster Intl. Airport (MBJ) to MDW?
Around 2,800 kilometres separates Montego Bay and Chicago, so pack something to keep you occupied for a few hours. That action-packed novel you're eager to read will do the trick.
Which airlines fly direct from Sir Donald Sangster Intl. Airport (MBJ) to Midway Airport?
Operating 4 flights monthly, Southwest Airlines (WN) is a top choice when flying directly from Sangster Intl. Airport to Chicago Airport.
Are Sir Donald Sangster Intl. Airport (MBJ) to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Sangster Intl. Airport to MDW at the last minute could save you some cash. However, you might miss out on a flight altogether! If you'd prefer not to take the risk, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains as far ahead as 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time.

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