Cheap Flights from Montego Bay to Chicago Midway

Compare Montego Bay to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Montego Bay to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Montego Bay Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $387. Find the lowest prices on one-way and return tickets right here.

Chicago.$387 per passenger.Departing Tue, 5 May, returning Tue, 19 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Montego Bay on Tue, 5 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 19 May, arriving in Montego Bay.Price includes taxes and charges.From $387, select.

Chicago.$490 per passenger.Departing Thu, 16 Jul, returning Tue, 28 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Montego Bay on Thu, 16 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Jul, arriving in Montego Bay.Price includes taxes and charges.From $490, select.

Chicago.$673 per passenger.Departing Thu, 30 Apr, returning Sat, 9 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Montego Bay on Thu, 30 Apr, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 9 May, arriving in Montego Bay.Price includes taxes and charges.From $673, select.

Chicago.$866 per passenger.Departing Sun, 19 Apr, returning Sun, 26 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Montego Bay on Sun, 19 Apr, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 26 Apr, arriving in Montego Bay.Price includes taxes and charges.From $866, select.

Chicago.$905 per passenger.Departing Wed, 27 May, returning Wed, 3 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Montego Bay on Wed, 27 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 3 Jun, arriving in Montego Bay.Price includes taxes and charges.From $905, select.

Chicago.$3,050 per passenger.Departing Thu, 3 Dec, returning Mon, 7 Dec.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Montego Bay on Thu, 3 Dec, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Mon, 7 Dec, arriving in Montego Bay.Price includes taxes and charges.From $3,050, select.

Find the cheapest month to fly from Montego Bay to Chicago Midway

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

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Direct flights from Montego Bay to Chicago Midway

Montego Bay to Chicago Midway: Alternative routes

Compare routes from Montego Bay to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Montego Bay to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$270
Cheapest month to fly	May
Average flight time	4 hrs, 5 mins
Most popular airline	Southwest Airlines
Average flights per week	2

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

How much are return flights from Montego Bay to Chicago Midway?

The best price we found for a return flight from Montego Bay to Chicago Midway is $387. 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.

How long does it take to fly from Montego Bay to Chicago Midway?

4 hours and 5 minutes is the average flight time from Montego Bay to Chicago Midway.

Which airlines fly direct from Montego Bay to Chicago Midway?

Southwest Airlines flies direct from Montego Bay to Chicago Midway.

How many flights are there a week from Montego Bay to Chicago Midway?

As of April 2026, there are 2 flights per week flying from Montego Bay to Chicago Midway.

When is the cheapest time to fly from Montego Bay to Chicago Midway?

The cheapest month to fly from Montego Bay to Chicago Midway is usually May.

Which upcoming date is cheapest to fly from Montego Bay Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Montego Bay Airport to Chicago Midway Airport on Tuesday, 5 May 2026.

Can I get a direct flight from Montego Bay Airport to Chicago Midway Airport?

Yes – the average flight time is 4 hours and 5 minutes.

How can I find the best flight deal to Chicago Midway?

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 Midway 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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Montego Bay Airport to Chicago Midway with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Flying from Sangster International Airport (MBJ) to Chicago Midway International Airport (MDW): what you need to know

Jump on a direct flight from Sangster International Airport to Chicago Midway International Airport and you'll be in the air for an average of 4 hours 15 minutes.
Montego Bay and Chicago are in the same timezone, UTC-5.
Get to the airport on time so you don't miss your MBJ to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid a last-minute sprint to the gate.
You can expect longer lines during popular months such as February. Arriving up to four hours in advance for an international flight and two hours for domestic departures is a good idea.
Southwest Airlines has direct flights from Sangster International Airport to Chicago Midway International Airport. Book with this popular carrier, then get ready to see the sights in Chicago — and maybe even more of United States if time allows.
The airline with the highest booking volume on this route is Southwest Airlines.
Southwest Airlines is the most punctual carrier operating MBJ to MDW flights.
If you'd like to include a stop along the way, just uncheck 'Direct flights only' when searching for your ticket from Sangster International Airport to Chicago Midway International Airport. Here are the top stopovers between MBJ and MDW:
- Hartsfield-Jackson Atlanta International Airport
- Charlotte Douglas International Airport
- Cleveland Hopkins International Airport

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

$270 is currently the lowest price for a one-way Sangster International Airport to Chicago Midway International Airport flight. A return flight starts at $387. These fares can change based on demand.
Book six months before travelling. After crunching the numbers on our calendar, this is how far you'll want to book ahead to secure cheap tickets from MBJ to MDW.
May is the cheapest month for flights from Sangster International Airport to Chicago Midway International Airport. If you're looking to travel during a different time of year, the 'Whole month' tool will give you the lowest prices for each month.
Picking up cheap flights from MBJ to MDW is a piece of cake with Price Alerts. All you need to do is set up one of these automatic alerts and we'll notify you as soon as a lower fare pops up.
Discover the perfect flight for you with the help of the filters. To see the 'Fastest,' 'Cheapest' or 'Best' flights from Sangster International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter results by airline, arrival and departure times, and journey duration.

Handy information about Sangster International Airport (MBJ)

74.59% of flights that take off from Sangster International Airport make it to their destination on schedule.
To reach Sangster International Airport from central Montego Bay, it takes around 10 minutes by car. This depends on traffic though. It's approximately 3 kilometres from the airport to the city centre.
Looking for a handy hotel close to MBJ? If you're boarding an early flight from Sangster International Airport to Chicago Midway International Airport, these stays will have you sleeping moments from your check-in counter:

Arriving at Chicago Midway International Airport (MDW)

If you're getting in on a late Sangster International Airport to Chicago Midway International Airport flight, few things beat the convenience of staying close to the terminal. Pick up your bags from the carousel and then be resting not long after at one of these hotels near MDW:
Pick up a Chicago Midway International Airport rental car and discover Chicago and beyond with your own wheels. Dollar, Hertz and Budget are popular providers to choose from here.
Lock in the best deal by booking your vehicle from Chicago Midway International Airport around four weeks ahead of your departure.

Getting from Chicago Midway International Airport (MDW) to central Chicago

MDW is located at 5700 South Cicero.
From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre by car.
It takes roughly 45 minutes if you're travelling by public transport.

When to fly to Chicago Midway International Airport (MDW)

It's time to choose your travel dates for your flight from Sangster International Airport to Chicago Midway International Airport. July is the busiest month to visit Chicago. If you're after a quieter vibe, go in May.
The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Book your flights from Sangster International Airport to Chicago Midway International Airport in this month if this is the type of weather you enjoy.
For cooler conditions, search for a cheap ticket from MBJ to MDW in January. Temperatures average between -12ºC and 3ºC then.

Explore more of United States

Chicago is easy to fall in love with, but there are so many other corners of United States you'll want to see. About 451 kilometres south-east of Chicago, a trip to Columbus will keep you on the go. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
If you're eager to discover another corner of United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are among its highlights.