$151 Cheap Flights from Montego Bay (MBJ) to Chicago (ORD)

View $151 flight on Tue, Sep 9, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

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

Prices were available within the past 7 days and start at $151 for one-way flights and $258 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
MBJ
Montego Bay
ORD
Chicago
$258 Roundtrip, found 6 hours ago
$258
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Montego Bay to Chicago, returning Sat, Aug 30, priced at $258 found 6 hours ago
Spirit Airlines
Thu, Aug 14 - Sat, Aug 23
MBJ
Montego Bay
ORD
Chicago
$266 Roundtrip, found 1 day ago
$266
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Aug 14 from Montego Bay to Chicago, returning Sat, Aug 23, priced at $266 found 1 day ago
Spirit Airlines
Thu, Sep 18 - Sat, Sep 27
MBJ
Montego Bay
ORD
Chicago
$268 Roundtrip, found 2 hours ago
$268
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Sep 18 from Montego Bay to Chicago, returning Sat, Sep 27, priced at $268 found 2 hours ago
Spirit Airlines
Thu, Aug 14 - Mon, Sep 1
MBJ
Montego Bay
ORD
Chicago
$269 Roundtrip, found 5 hours ago
$269
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Thu, Aug 14 from Montego Bay to Chicago, returning Mon, Sep 1, priced at $269 found 5 hours ago
Spirit Airlines
Thu, Aug 14 - Fri, Aug 15
MBJ
Montego Bay
ORD
Chicago
$278 Roundtrip, found 10 hours ago
$278
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Thu, Aug 14 from Montego Bay to Chicago, returning Fri, Aug 15, priced at $278 found 10 hours ago
Spirit Airlines
Wed, Sep 10 - Mon, Sep 15
MBJ
Montego Bay
ORD
Chicago
$280 Roundtrip, found 15 hours ago
$280
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Wed, Sep 10 from Montego Bay to Chicago, returning Mon, Sep 15, priced at $280 found 15 hours ago
American Airlines
Fri, Aug 29 - Tue, Sep 2
MBJ
Montego Bay
ORD
Chicago
$311 Roundtrip, found 10 hours ago
$311
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Fri, Aug 29 from Montego Bay to Chicago, returning Tue, Sep 2, priced at $311 found 10 hours ago
Frontier Airlines
Sat, Nov 8 - Sat, Nov 15
MBJ
Montego Bay
ORD
Chicago
$332 Roundtrip, found 5 days ago
$332
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Nov 8 from Montego Bay to Chicago, returning Sat, Nov 15, priced at $332 found 5 days ago
United
Wed, Oct 22 - Sun, Oct 26
MBJ
Montego Bay
ORD
Chicago
$344 Roundtrip, found 8 hours ago
$344
Roundtrip
found 8 hours ago
Select United flight, departing Wed, Oct 22 from Montego Bay to Chicago, returning Sun, Oct 26, priced at $344 found 8 hours ago
Delta
Wed, Oct 22 - Sun, Oct 26
MBJ
Montego Bay
ORD
Chicago
$348 Roundtrip, found 8 hours ago
$348
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Oct 22 from Montego Bay to Chicago, returning Sun, Oct 26, priced at $348 found 8 hours ago

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

February is typically the cheapest month to fly

From $237 - $498 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 Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $388
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $388
Flights from Montego Bay (MBJ) to Chicago (ORD)
Origin airport
Sir Donald Sangster Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Copa, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$258
Distance
1725 mi
Average flight time
5 hours 30 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 August. 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 $151 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 O'Hare Intl. Airport (ORD) cost?
You can score cheap return tickets from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD) starting from $334. Book a seat and be on your way. 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 American Airlines flight leaving MBJ on August 15 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from MBJ to ORD?
The cheapest flights from MBJ to ORD 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 O'Hare Intl. Airport (ORD)?
Jump on a direct flight with United Airlines and head straight from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from MBJ to ORD?
With fares starting at $210 for a one-way flight from MBJ to ORD, American Airlines is currently the cheapest airline for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MBJ on August 28 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 O'Hare Intl. Airport (ORD)?
On average, you'll only find 1 direct flight operating from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD) per day. If this doesn't fit your travel plans, consider flights with layovers. Just filter your search on Expedia to include one stop or more to discover the next best option.
What are the most popular departure times for flights from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD)?
More travelers fly between MBJ and ORD at 2 PM than at any other time of day. Rather skip the crowds? Travel outside of rush hours and there's a chance you'll save on your ticket as well.
What day of the week has the most flights from MBJ to ORD?
If you travel on a Saturday, you'll get the widest range of options for flights from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD)?
The earliest flight out of Sir Donald Sangster Intl. Airport (MBJ) is at around 1:15PM UTC-5. Board this plane and you'll reach O'Hare Intl. Airport (ORD) at approximately 4:50PM UTC-6. The total travel time is 4h 35m.
How long does it take to fly from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD)?
Flights from MBJ to ORD have an average travel time of 4 hours and 25 minutes. The distance between the two airports is 1,750 mi.
What is the best time to fly from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD)?
Choose a flight from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the likelihood of delays and cancellations. 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 traveling on a direct flight from Sir Donald Sangster Intl. Airport (MBJ) to Chicago, you can 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 O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from MBJ to ORD are generally more expensive. For the best rates, start looking for flights early. That said, if your travel plans are flexible, it's possible to find a cheap fare right before your trip.
Is it cheaper to book a MBJ to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a MBJ to ORD flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one convenient place takes the hassle out of travel planning. Simply secure your flights and choose from our extensive range of hotels, then tailor your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD)?
If you reserved your MBJ to ORD flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. 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.

Explore a world of travel with Expedia

*Available to One Key members.