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CA $441 Cheap Flights from Montego Bay (MBJ) to Chicago (MDW)

View CA $441 flight on Sat, Oct 31, 2026Opens 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 $441 for one-way flights and CA $1,499 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $1,499 Roundtrip, found 6 days ago
CA $1,499
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $1,499 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $1,712 Roundtrip, found 6 days ago
CA $1,712
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $1,712 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $1,772 Roundtrip, found 6 days ago
CA $1,772
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $1,772 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $1,904 Roundtrip, found 6 days ago
CA $1,904
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $1,904 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $1,985 Roundtrip, found 6 days ago
CA $1,985
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $1,985 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $2,053 Roundtrip, found 6 days ago
CA $2,053
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $2,053 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $2,100 Roundtrip, found 6 days ago
CA $2,100
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $2,100 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $2,176 Roundtrip, found 6 days ago
CA $2,176
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $2,176 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $2,254 Roundtrip, found 6 days ago
CA $2,254
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $2,254 found 6 days ago
Delta
Fri, Jul 10 - Wed, Jul 15
MBJ
Montego Bay
MDW
Chicago
CA $2,302 Roundtrip, found 6 days ago
CA $2,302
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 10 from Montego Bay to Chicago, returning Wed, Jul 15, priced at CA $2,302 found 6 days ago

Frequently asked questions

How much does a flight from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from MBJ to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when MBJ to MDW ticket fares go up or down.
What is the cheapest month to fly from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from MBJ to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
Only one airline offers direct flights from Montego Bay (MBJ) to Chicago, IL (MDW). Southwest Airlines operates 7 direct flights from MBJ to MDW every week.
What is the cheapest airline that flies from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering nonstop return flights from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$388 for flights that can be booked for departure within the next year. Frontier Airlines offers one of the cheapest connecting return flights on this route, with tickets starting from around CA$515. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Southwest Airlines offers early morning flights. If price is the most important factor, Southwest Airlines typically offers the lowest fares. Southwest Airlines offers the most daily flights from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
While direct flights are limited, you'll find approximately 9 connecting flights per day from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.). Some common connection points include Orlando Intl. (MCO), Baltimore Washington Intl. Thurgood Marshall (BWI), and William P. Hobby (HOU).
What is the earliest flight from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 8:00 AM. This service is operated by Delta and is a seasonal offering, active only in December. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) on a Tuesday, with around 8 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Southwest Airlines, Delta, and Frontier Airlines. Flight schedules are fairly consistent throughout the week, so you should find suitable options on other days as well.
What are the most popular departure times for flights from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) are between 12pm and 3pm. Many major carriers, including Southwest Airlines, Delta and Frontier Airlines, offer flights during this window. This timing works well for travellers who prefer a midday departure, allowing for a relaxed morning before heading to the airport.
How long does it take to fly from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) typically takes around 4 hours, covering a distance of approximately 2,752 kilometers. If you opt for a flight with one stop, your travel time will be significantly longer, usually around 19 hours 48 minutes. Flights with two or more stops generally take about 18 hours 18 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.
Can you fly business or first class from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class from Montego Bay (MBJ) to Chicago, IL (MDW). However, it's important to note that only Frontier Airlines offers business class service on this route.
How do I earn miles on a Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (MDW) from Montego Bay (MBJ)?
If you're planning to travel to Chicago from Sir Donald Sangster Intl. (MBJ), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Orlando Intl. (MCO), or William P. Hobby (HOU) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Montego Bay (MBJ-Sir Donald Sangster Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. 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, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Sir Donald Sangster Intl.
Destination airport
Midway Intl.
Roundtrip price
CA $1,498
Distance
2735 km

Book with confidence

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 CA $1,499 rising to CA $2,302.  

Here are more money-saving tips: 

  • Fly in July 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.

Montego Bay to Chicago Flights

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