Cheap Flights from Chicago Midway to Montego Bay

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Flight deals from Chicago Midway to Montego Bay

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

Montego Bay.$521 per passenger.Departing Tue, 3 Mar, returning Fri, 6 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 3 Mar, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Fri, 6 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $521, select.

Montego Bay.$521 per passenger.Departing Tue, 28 Apr, returning Fri, 1 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 28 Apr, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Fri, 1 May, arriving in Chicago Midway.Price includes taxes and charges.From $521, select.

Montego Bay.$529 per passenger.Departing Sun, 3 May, returning Tue, 12 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 3 May, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Tue, 12 May, arriving in Chicago Midway.Price includes taxes and charges.From $529, select.

Montego Bay.$627 per passenger.Departing Sat, 25 Apr, returning Tue, 28 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 25 Apr, arriving in Montego Bay.Inbound indirect flight with Delta, departs from Montego Bay on Tue, 28 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $627, select.

Montego Bay.$632 per passenger.Departing Sat, 11 Apr, returning Sat, 18 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 11 Apr, arriving in Montego Bay.Inbound direct flight with Southwest Airlines departs from Montego Bay on Sat, 18 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $632, select.

Montego Bay.$659 per passenger.Departing Sun, 15 Mar, returning Sun, 22 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 15 Mar, arriving in Montego Bay.Inbound direct flight with Southwest Airlines departs from Montego Bay on Sun, 22 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $659, select.

Montego Bay.$682 per passenger.Departing Fri, 27 Feb, returning Fri, 6 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 27 Feb, arriving in Montego Bay.Inbound indirect flight with Delta, departs from Montego Bay on Fri, 6 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $682, select.

Montego Bay.$716 per passenger.Departing Sat, 22 Aug, returning Sat, 29 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 22 Aug, arriving in Montego Bay.Inbound indirect flight with Delta, departs from Montego Bay on Sat, 29 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $716, select.

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

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

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Direct flights from Chicago Midway to Montego Bay

Chicago Midway to Montego Bay: Alternative routes

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

Montego Bay

3km from central Montego Bay

ClosestCheapest

from $521

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Chicago to Montego Bay: Flight information

The things to know before you go.

Cheapest flight found	$521
Cheapest month to fly	April
Average flight time	3 hrs, 51 mins
Most popular airline	Southwest Airlines
Average flights per week	4

Check out these Montego Bay hotels

Ready to plan your stay? Other travellers rate these Montego Bay hotels for cleanliness, service and location.

Airport Beach Hotel

1.46 km from Montego Bay

$167

Per night

Palm View Guesthouse and Conference Centre

1.54 km from Montego Bay

$95

Per night

Gloriana Hotel

1.81 km from Montego Bay

$203

Per night

Airport Beach Hotel

1.46 km from Montego Bay

$167

Per night

Palm View Guesthouse and Conference Centre

1.54 km from Montego Bay

$95

Per night

Gloriana Hotel

1.81 km from Montego Bay

$203

Per night

Explore top-rated hotels

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

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

The best price we found for a return flight from Chicago Midway to Montego Bay is $521. 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 Chicago Midway to Montego Bay?

3 hours and 51 minutes is the average flight time from Chicago Midway to Montego Bay.

Which airlines fly direct from Chicago Midway to Montego Bay?

Southwest Airlines flies direct from Chicago Midway to Montego Bay.

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

As of February 2026, there are 4 flights per week flying from Chicago Midway to Montego Bay.

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

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

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Montego Bay Airport on Tuesday, 28 April 2026.

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

Yes – the average flight time is 3 hours and 51 minutes.

How can I find the best flight deal to Montego Bay?

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 Montego Bay 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 Montego Bay?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Montego Bay is around 40 days in advance, so don’t leave your flight to the last minute.

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

Currently, Southwest Airlines offers the cheapest flight tickets to Montego Bay.

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

The average length of a direct flight from Chicago Midway International Airport to Sangster International Airport is 4 hours.
Chicago and Montego Bay share the same timezone, UTC-5.
Get to the airport on time so you don't miss your MDW to MBJ flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.
You'll likely experience longer lines in popular months like July. Arriving up to four hours ahead of an international flight and two hours for a domestic departure will give you ample time for security and boarding.
Southwest Airlines has direct flights from Chicago Midway International Airport to Sangster International Airport. Book with this popular carrier, then get ready to discover the sights in Montego Bay — and maybe even more of Jamaica if you have time.
The majority of travellers choose to travel with Southwest Airlines on this route.
With 66.67% of its services arriving as planned, Southwest Airlines is the most punctual carrier operating MDW to MBJ flights.
We make it a cinch to book a flight with a stopover. To see your options for tickets from Chicago Midway International Airport to Sangster International Airport, deselect 'Direct flights only.' Then, choose a flight with a stop long enough to visit the city of your choice. Popular stopovers between MDW and MBJ include:
- Hartsfield-Jackson Atlanta International Airport
- Charlotte Douglas International Airport
- Orlando International Airport

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

At the moment, $221 is the lowest price we've found for a one-way Chicago Midway International Airport to Sangster International Airport flight. The best price for a return ticket is $521. Bear in mind that fares can change due to availability when booking.
Book six months before travelling. After crunching the numbers on our calendar, this is how far you should book ahead to secure cheap tickets from MDW to MBJ.
Organise your trip for May. That's the cheapest month for flights from Chicago Midway International Airport to Sangster International Airport. If you're flexible with your dates, use the 'Whole month' tool to find the lowest airfare across each month.
Finding cheap flights from MDW to MBJ is a piece of cake with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know as soon as there's a better deal.
Secure the ideal flight for you with the help of the filters. To see the 'Best,' 'Fastest' or 'Cheapest' flights from Chicago Midway International Airport to Sangster International Airport, use the 'Sort by' tool. You can also filter by arrival and departure times, airline, and number of stops.

Handy information about Chicago Midway International Airport (MDW)

MDW's address is 5700 South Cicero.
When it comes to the on-time performance of Chicago Midway International Airport, data shows 77.88% of flights arrive within the expected timeframe.
Chicago Midway International Airport is about 19 kilometres from central Chicago. If you're catching a cab, ride-sharing or driving from the centre, it'll take 20 minutes or so to arrive, depending on the traffic.
Expect a trip time of around 45 minutes on public transport.
Get your holiday off to a hassle-free start by staying near MDW. Whether you're catching an early flight from Chicago Midway International Airport to Sangster International Airport or want to avoid feeling rushed, these stays have you covered:

Arriving at Sangster International Airport (MBJ)

Book a hotel close to MBJ if you're catching a late Chicago Midway International Airport to Sangster International Airport flight. Check in to one of these options and skip the long transfer:
Grab a Sangster International Airport rental car and explore Montego Bay and beyond with your own wheels. Classique, Island Car Rentals and FlexWays are popular outlets you can book with here.
For the best deal, book your ride from Sangster International Airport around three weeks before you travel.

Getting from Sangster International Airport (MBJ) to central Montego Bay

Sangster International Airport is roughly 3 kilometres from the centre of Montego Bay. The drive time takes around 10 minutes.

When to fly to Sangster International Airport (MBJ)

It's time to pick your trip dates for your flight from Chicago Midway International Airport to Sangster International Airport. February is the most popular month to head to Montego Bay. If you like a more laid-back vibe, go in May.
When reserving your flight from Chicago Midway International Airport to Sangster International Airport, consider the type of weather you enjoy. August is the warmest month in Montego Bay, with the temperature ranging from 25ºC to 31ºC.
If you want to travel in cooler conditions, look for a cheap ticket from MDW to MBJ in February. Temperatures average between 22ºC and 28ºC then.

Explore more of Jamaica

Montego Bay has loads to offer, but there are so many other parts of Jamaica waiting to be explored. About 129 kilometres south-east of Montego Bay, a trip to Kingston will fill your itinerary to the brim. Start with attractions like Devon House, Blue Mountains and Emancipation Park.
Spanish Town is another standout destination in Jamaica and is around 113 kilometres south-east of Montego Bay. No journey is complete without dropping by Angels Plaza, Cowan's Plaza and Michael Paul Barker Estate.