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

View $151 flight on Fri, Oct 31, 2025Opens in a new window

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

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 $215 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Nov 8 - Tue, Nov 11
MBJ
Montego Bay
ORD
Chicago
$215 Roundtrip, found 6 hours ago
$215
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Sat, Nov 8 from Montego Bay to Chicago, returning Tue, Nov 11, priced at $215 found 6 hours ago
Spirit Airlines
Sat, Nov 8 - Tue, Nov 11
MBJ
Montego Bay
ORD
Chicago
$231 Roundtrip, found 6 hours ago
$231
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Sat, Nov 8 from Montego Bay to Chicago, returning Tue, Nov 11, priced at $231 found 6 hours ago
Spirit Airlines
Thu, Oct 23 - Wed, Oct 29
MBJ
Montego Bay
ORD
Chicago
$232 Roundtrip, found 3 days ago
$232
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Oct 23 from Montego Bay to Chicago, returning Wed, Oct 29, priced at $232 found 3 days ago
Spirit Airlines
Sat, Oct 25 - Mon, Oct 27
MBJ
Montego Bay
ORD
Chicago
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Oct 25 from Montego Bay to Chicago, returning Mon, Oct 27, priced at $234 found 4 days ago
Spirit Airlines
Wed, Oct 22 - Mon, Oct 27
MBJ
Montego Bay
ORD
Chicago
$239 Roundtrip, found 6 days ago
$239
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Oct 22 from Montego Bay to Chicago, returning Mon, Oct 27, priced at $239 found 6 days ago
Spirit Airlines
Fri, Oct 31 - Sun, Nov 9
MBJ
Montego Bay
ORD
Chicago
$243 Roundtrip, found 20 hours ago
$243
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Fri, Oct 31 from Montego Bay to Chicago, returning Sun, Nov 9, priced at $243 found 20 hours ago
United
Fri, Dec 19 - Wed, Jan 7
MBJ
Montego Bay
ORD
Chicago
$320 Roundtrip, just found
$320
Roundtrip
just found
Select United flight, departing Fri, Dec 19 from Montego Bay to Chicago, returning Wed, Jan 7, priced at $320 just found
American Airlines
Fri, Jan 23 - Mon, Jan 26
MBJ
Montego Bay
ORD
Chicago
$330 Roundtrip, found 1 hour ago
$330
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Jan 23 from Montego Bay to Chicago, returning Mon, Jan 26, priced at $330 found 1 hour ago
Delta
Thu, Dec 4 - Mon, Dec 8
MBJ
Montego Bay
ORD
Chicago
$335 Roundtrip, found 2 hours ago
$335
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Dec 4 from Montego Bay to Chicago, returning Mon, Dec 8, priced at $335 found 2 hours ago
Southwest Airlines
Thu, Dec 4 - Tue, Dec 9
MBJ
Montego Bay
ORD
Chicago
$335 Roundtrip, found 9 hours ago
$335
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Montego Bay to Chicago, returning Tue, Dec 9, priced at $335 found 9 hours ago

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

September is typically the cheapest month to fly

From $227 - $480 per traveler.

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 $563
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $563

Frequently asked questions

How much does a flight from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $151 or cheap return flight from $215 from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD)?
Planning your getaway for November can help you save, as it's the cheapest month for flights between MBJ and ORD. You'll usually find the lowest prices during the off-season.
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 Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Sir Donald Sangster Intl. Airport (MBJ) and O'Hare Intl. Airport (ORD) can change depending on when you plan to fly. American Airlines and United Airlines are just some of the choices offering competitive fares. Use Expedia's filter tool to compare airlines in one place and find the right MBJ to ORD flight for your budget.
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.

Travel information

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
$215
Distance
1725 mi
Average flight time
5 hours 33 mins

Book with confidence

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 November. 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.

 

Montego Bay to Chicago Flights

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*Available to One Key members.