$125 Cheap Flights from Chicago (ORD) to Montego Bay (MBJ)

View $125 flight on Tue, Sep 30, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)

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

Prices were available within the past 7 days and start at $125 for one-way flights and $276 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Aug 13 - Tue, Aug 19
ORD
Chicago
MBJ
Montego Bay
$276 Roundtrip, found 4 hours ago
$276
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Aug 13 from Chicago to Montego Bay, returning Tue, Aug 19, priced at $276 found 4 hours ago
Spirit Airlines
Thu, Aug 21 - Wed, Aug 27
ORD
Chicago
MBJ
Montego Bay
$286 Roundtrip, found 4 hours ago
$286
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, Aug 21 from Chicago to Montego Bay, returning Wed, Aug 27, priced at $286 found 4 hours ago
Spirit Airlines
Tue, Jul 29 - Thu, Jul 31
ORD
Chicago
MBJ
Montego Bay
$293 Roundtrip, found 13 hours ago
$293
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Tue, Jul 29 from Chicago to Montego Bay, returning Thu, Jul 31, priced at $293 found 13 hours ago
Spirit Airlines
Sun, Aug 31 - Sat, Sep 6
ORD
Chicago
MBJ
Montego Bay
$296 Roundtrip, found 2 hours ago
$296
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Aug 31 from Chicago to Montego Bay, returning Sat, Sep 6, priced at $296 found 2 hours ago
Spirit Airlines
Thu, Sep 25 - Wed, Oct 1
ORD
Chicago
MBJ
Montego Bay
$306 Roundtrip, found 4 hours ago
$306
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, Sep 25 from Chicago to Montego Bay, returning Wed, Oct 1, priced at $306 found 4 hours ago
Spirit Airlines
Mon, Aug 18 - Sun, Aug 24
ORD
Chicago
MBJ
Montego Bay
$311 Roundtrip, found 4 hours ago
$311
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Mon, Aug 18 from Chicago to Montego Bay, returning Sun, Aug 24, priced at $311 found 4 hours ago
American Airlines
Tue, Oct 7 - Fri, Oct 10
ORD
Chicago
MBJ
Montego Bay
$370 Roundtrip, just found
$370
Roundtrip
just found
Select American Airlines flight, departing Tue, Oct 7 from Chicago to Montego Bay, returning Fri, Oct 10, priced at $370 just found
Delta
Tue, Sep 23 - Wed, Oct 1
ORD
Chicago
MBJ
Montego Bay
$385 Roundtrip, just found
$385
Roundtrip
just found
Select Delta flight, departing Tue, Sep 23 from Chicago to Montego Bay, returning Wed, Oct 1, priced at $385 just found
United
Mon, Sep 22 - Tue, Sep 30
ORD
Chicago
MBJ
Montego Bay
$385 Roundtrip, just found
$385
Roundtrip
just found
Select United flight, departing Mon, Sep 22 from Chicago to Montego Bay, returning Tue, Sep 30, priced at $385 just found
Southwest Airlines
Wed, Oct 1 - Wed, Oct 8
ORD
Chicago
MBJ
Montego Bay
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Chicago to Montego Bay, returning Wed, Oct 8, priced at $389 found 1 day ago

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

October is typically the cheapest month to fly

From $262 - $471 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (ORD) to Montego Bay (MBJ)
Origin airport
O'Hare Intl.
Destination airport
Sir Donald Sangster Intl.
Airlines serving
Air Canada, American Airlines, Copa, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$276
Distance
1725 mi
Average flight time
4 hours 2 mins

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 August. 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 $125 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 O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ) cost?
Cheap round-trip flights from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ) start at $370. 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 United flight leaving ORD on July 7 2025 and touching down at MBJ. The price was last updated on June 29 2025 and has not changed since.
What is the cheapest month to fly from ORD to MBJ?
The cheapest flights from ORD 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 O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)?
Catch a direct flight with United Airlines and head straight from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ).
What is the cheapest airline that flies from ORD to MBJ?
Take off from ORD to MBJ with United. This airline currently offers the lowest one-way fare for this route, starting at $164. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on August 17 2025. Prices were last updated on June 29 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)?
On average, just 1 nonstop flight departs daily from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ). Seeking more options? Use Expedia's filter tool to find flights with layovers and explore a new city along the way.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)?
The 8 AM departures from ORD to MBJ are the busiest. Prices can be higher for these popular slots. If you're looking to save, pick a less crowded time to fly.
What day of the week has the most flights from ORD to MBJ?
Saturday offers the most flights from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ). Consider traveling on this day and you'll have a greater chance of finding a departure that works with your plans.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)?
The earliest flight departing from O'Hare Intl. Airport (ORD) is at around 7:05AM UTC-6. Board this flight and you'll arrive at Sir Donald Sangster Intl. Airport (MBJ) at approximately 12:15PM UTC-5. The total travel time is 4h 10m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)?
It takes approximately 4 hours and 6 minutes to cover the 1,750 mi from ORD to MBJ.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)?
To land at Sir Donald Sangster Intl. Airport (MBJ) without delays, select a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 O'Hare Intl. Airport (ORD)?
Sir Donald Sangster Intl. Airport (MBJ) is the only airport in Montego Bay with direct flights from O'Hare Intl. Airport (ORD). Compare your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ) last-minute?
Booking your plane ticket from ORD to MBJ just before your trip is typically more expensive. However, if there's some wiggle room with your travel times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book an ORD to MBJ flight and hotel package?
Booking an ORD to MBJ flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our extensive range of hotels and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Sir Donald Sangster Intl. Airport (MBJ)?
If you booked your ORD to MBJ flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

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*Available to One Key members.