Cheap flights from Montego Bay to Chicago

Compare Montego Bay to Chicago flight deals

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Flight deals from Montego Bay to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Montego Bay to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Montego Bay to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Montego Bay to Chicago flights are currently cheapest in September.

Direct flights from Montego Bay to Chicago

Alternative Montego Bay to Chicago routes

Looking for the cheapest, fastest or easiest route from Montego Bay to Chicago? You could fly into the following airports instead.

Montego Bay to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$325
Cheapest month to flySeptember
Average flight time4 hrs, 22 mins
Most popular airlineAmerican Airlines
Average flights per week22

Finding cheap flights from Montego Bay to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Montego Bay to Chicago is C$324. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 21 minutes is the average flight time from Montego Bay to Chicago.
American Airlines, British Airways and United fly direct from Montego Bay to Chicago.
There are 44 flights per week flying from Montego Bay to Chicago, as of August 2025.
The cheapest month to fly from Montego Bay to Chicago is usually September.
If you're flying from Montego Bay Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from C$324.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Montego Bay Airport to Chicago on Wednesday, September 10, 2025.
Yes – the average flight time is 4 hours and 21 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In August, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Spirit Airlines and United offer the cheapest flight tickets to Chicago.

Travelling from Sangster International Airport (MBJ) to Chicago: what you need to know

  • Around 4 hours 5 minutes is how long you can expect to be in the air on a direct flight from Sangster International Airport to Chicago.

  • Montego Bay (the location of Sangster International Airport) and Chicago share the same timezone — UTC-5.

  • With 12 weekly flights between the two airports, Sangster International Airport (MBJ) to O'Hare International Airport (ORD) is the busiest route. American Airlines operates the earliest flight at 12:13. If you're eager to make the most of your day before flying, the latest flight from MBJ to ORD is with American Airlines at 15:30.

  • Give yourself enough time to make your MBJ to Chicago flight. It's generally best to arrive two hours before international departures and an hour ahead for domestic flights.

  • Longer lines at security and check-in are likely if you're flying during high season, so give yourself some extra breathing room. A good rule for peak times? Get there up to four hours early for international flights and at least two hours for domestic departures.

  • Begin your journey at MBJ and fly nonstop to O'Hare International Airport (ORD). That will be your arrival point when searching for Sangster International Airport to Chicago tickets.

  • Pick from a variety of carriers that offer direct flights from Sangster International Airport to Chicago. Book your journey with one of these:

  • Stopovers are the ideal opportunity to break up your trip and possibly even explore another city. When browsing for flight tickets from MBJ to Chicago, uncheck the 'Direct flights only' box to see where you can visit along the way. Some popular options include:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Charlotte Douglas International Airport (CLT)

    • Detroit Metropolitan Wayne County Airport (DTW)

  • To get to MBJ from central Montego Bay, it takes around 10 minutes if you're travelling by car. It's roughly 3 kilometres from the airport to the city centre.

  • Want a hassle-free start to your journey? Stay near MBJ. Whether you have an early flight from Sangster International Airport to Chicago or want to avoid feeling rushed, these hotels have you covered:

  • 74.59% of flights that leave from Sangster International Airport touch down at their destination on time.

How to find the cheapest flights from Sangster International Airport (MBJ) to Chicago

  • C$202 is the cheapest price we've found for a one-way Sangster International Airport to Chicago flight. A round-trip ticket right now is C$324. Depending on how early you book and the availability, these fares may change.

  • To pick up cheap flights from MBJ to Chicago, book your journey one month before your departure date.

  • May is the best month for picking up a fantastic deal on Sangster International Airport to Chicago tickets. If you'd like to travel during a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • Cut down on the time spent looking for cheap flights from MBJ to Chicago by creating a Price Alert. You'll receive an email or notification through the app when a special offer becomes available.

  • Pick your ideal departure and arrival times, airlines and number of stops with our filters. Then, sort the results for your flight from Sangster International Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you around 35 minutes to reach the centre driving.

  • If you're using public transport, expect a journey time of about 55 minutes.

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Sangster International Airport to Chicago. Stay at one of these accommodation options near ORD instead:

  • Hit the road running by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's usual tourist stops.

  • For the best deal, reserve your vehicle from O'Hare International Airport around four weeks in advance of your flight from MBJ to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Sangster International Airport to Chicago has hit the tarmac, you can make your way to the city centre in about 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • If you choose to travel on public transport, you'll get to the city centre in 45 minutes or so.

  • Hang the 'Do not disturb' sign on your door and unwind at a hotel close to MDW. Here are a few options where you can settle in after your MBJ to Chicago flight:

  • No time to waste? The fastest way to get to where you're going is with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and hit the road in a heartbeat.

  • Secure your first choice, not your last resort. Booking your ride from MDW four weeks in advance often means lower prices and a wider selection of vehicles.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from the centre of Chicago. It takes about 1 hour 25 minutes to reach the city centre in a cab or ride-share once you've hopped off your flight from Sangster International Airport to Chicago.

  • The journey will take roughly 4 hours 15 minutes using public transport.

  • If you don't want to make your way into the centre, find a hotel near RFD. Get settled at one of these options after your MBJ to Chicago flight:

  • Be in the driver's seat of the next part of your trip by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are dependable companies for booking.

  • Booking a couple of weeks ahead of your flight from Sangster International Airport to Chicago is a smart move. In addition to better deals, you'll have a wider selection of vehicle makes and models at RFD.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your trip dates before securing your flight from Sangster International Airport to Chicago. The city comes alive during high season, but hotel prices are typically higher and major attractions can get crowded. Go to Chicago in low season if you like a more relaxed vibe.

  • Before locking in your Sangster International Airport to Chicago flight ticket, think about the kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from MBJ to Chicago around that time if you want to travel in cooler conditions.

More about Chicago

  • Once you've booked your flight from Sangster International Airport to Chicago, choose a hotel that puts you right where the action is. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to discover in this city it can be difficult to know where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top sights which should be on every Chicago itinerary.

Explore more of United States

  • Chicago has its own special appeal, but there are so many other corners of United States just waiting to be explored. About 451 kilometres south-east of Chicago, a trip to Columbus will keep your itinerary packed. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.