Cheap Flights from Chicago Midway to Montego Bay

Compare Chicago Midway to Montego Bay flight deals

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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 Airport to Montego Bay Airport? If you want to travel next month, return fares start from $786. Find the lowest prices on one-way and return tickets right here.

Montego Bay.$655 per passenger.Departing Mon, 2 Nov, returning Thu, 5 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 2 Nov, arriving in Montego Bay.Inbound indirect flight with Delta, departs from Montego Bay on Thu, 5 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $655, select.

Montego Bay.$688 per passenger.Departing Sun, 20 Sep, returning Wed, 23 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 20 Sep, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Wed, 23 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $688, select.

Montego Bay.$690 per passenger.Departing Sat, 31 Oct, returning Sat, 7 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 31 Oct, arriving in Montego Bay.Inbound indirect flight with Delta, departs from Montego Bay on Sat, 7 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $690, select.

Montego Bay.$786 per passenger.Departing Sun, 23 Aug, returning Sat, 29 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 23 Aug, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Sat, 29 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $786, select.

Montego Bay.$819 per passenger.Departing Fri, 4 Dec, returning Mon, 7 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 4 Dec, arriving in Montego Bay.Inbound indirect flight with Delta, departs from Montego Bay on Mon, 7 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $819, select.

Montego Bay.$829 per passenger.Departing Mon, 26 Oct, returning Fri, 30 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 26 Oct, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Fri, 30 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $829, select.

Montego Bay.$830 per passenger.Departing Sun, 30 Aug, returning Sun, 6 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 30 Aug, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Sun, 6 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $830, select.

Montego Bay.$844 per passenger.Departing Sat, 26 Sep, returning Thu, 1 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 26 Sep, arriving in Montego Bay.Inbound indirect flight with Frontier Airlines, departs from Montego Bay on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $844, select.

Montego Bay.$867 per passenger.Departing Fri, 27 Nov, returning Wed, 2 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 27 Nov, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Wed, 2 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $867, select.

Montego Bay.$1,002 per passenger.Departing Tue, 19 Jan, returning Fri, 22 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 19 Jan, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Fri, 22 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $1,002, select.

Montego Bay.$1,009 per passenger.Departing Sat, 6 Feb, returning Wed, 10 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 6 Feb, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Wed, 10 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $1,009, select.

Montego Bay.$1,088 per passenger.Departing Mon, 12 Apr, returning Fri, 16 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 12 Apr, arriving in Montego Bay.Inbound indirect flight with Delta, departs from Montego Bay on Fri, 16 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $1,088, select.

Montego Bay.$1,129 per passenger.Departing Wed, 27 Jan, returning Sat, 6 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 27 Jan, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Sat, 6 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $1,129, select.

Montego Bay.$1,146 per passenger.Departing Wed, 3 Mar, returning Sun, 7 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 3 Mar, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Sun, 7 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $1,146, select.

Montego Bay.$1,174 per passenger.Departing Sat, 25 Jul, returning Sat, 1 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 25 Jul, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Sat, 1 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $1,174, select.

Montego Bay.$1,297 per passenger.Departing Wed, 30 Dec, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 30 Dec, arriving in Montego Bay.Inbound indirect flight with Southwest Airlines, departs from Montego Bay on Tue, 5 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $1,297, 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 November.

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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 $655

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Chicago to Montego Bay: Flight information

The things to know before you go.

Cheapest flight found	$655
Cheapest month to fly	November
Average flight time	3 hrs, 58 mins
Most popular airline	Southwest Airlines
Average flights per week	2

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 $655. 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 58 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 July 2026, there are 2 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 November.

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 Monday, 2 November 2026.

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

Yes – the average flight time is 3 hours and 58 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, Delta and Southwest Airlines offer the cheapest flight tickets to Montego Bay.

Flying from Chicago Midway Airport (MDW) to Montego Bay Airport (MBJ): what you need to know

Take a direct flight from Chicago Midway Airport to Montego Bay Airport and you'll be travelling for an average of 3 hours 50 minutes.
Montego Bay's timezone is UTC-5, which makes Montego Bay one hour ahead of Chicago.
Leave enough time to catch your MDW to MBJ flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.
Be prepared for bigger queues in popular months such as July. Arriving up to four hours ahead of international flights and two hours for a domestic departure is a smart move.
Getting to Montego Bay (and then discovering more of Jamaica!) is a snap with Southwest Airlines. This popular carrier has direct flights from Chicago Midway Airport to Montego Bay Airport.
Most passengers choose to travel with Southwest Airlines on this route.
Southwest Airlines is the most punctual carrier that operates MDW to MBJ flights, with 66.67% of its services arriving as scheduled.
If you'd like to include a stop along the way, simply uncheck 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Montego Bay Airport. Here are the top stopovers between MDW and MBJ:
- Atlanta Hartsfield-Jackson Airport
- Charlotte Douglas Airport
- Orlando International Airport

How to find the cheapest flights from Chicago Midway Airport (MDW) to Montego Bay Airport (MBJ)

The cheapest price we've found for a one-way Chicago Midway Airport to Montego Bay Airport flight is $286. A round-trip fare is currently $655. Depending on the availability when you book, these fares can change.
To score cheap tickets from MDW to MBJ, book ahead. Airlines usually offer their most competitively priced fares when flights are first made available.
May is the cheapest month for flights from Chicago Midway Airport to Montego Bay Airport. If you want to fly during a different time of year, the 'Whole month' tool will show you the lowest airfares for each month.
There's no need to check back in every day to see if fares have dropped when you set up a Price Alert. We'll let you know as soon as there's a better deal on cheap flights from MDW to MBJ.
Tailor your trip with filters. Pick your preferred departure and arrival times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Chicago Midway Airport to Montego Bay Airport.

Handy information about Chicago Midway Airport (MDW)

The address for MDW is 5700 South Cicero.
Of the departures from Chicago Midway Airport, 76% land on time at their destination.
To get to Chicago Midway Airport from central Chicago, it'll take about 25 minutes if you're planning to drive. This depends on traffic though. It's approximately 16 kilometres from the airport to the city centre.
The trip when using public transport typically takes 30 minutes.
Booked an early flight from Chicago Midway Airport to Montego Bay Airport? Avoid the last-minute rush to the terminal (and sneak in some extra precious sleep) by picking one of these stays close to MDW:

Arriving at Montego Bay Airport (MBJ)

The last thing you need is a long trip to your hotel if you're landing late on a Chicago Midway Airport to Montego Bay Airport flight. Stay at one of these accommodation options near MBJ instead:
Grab a Montego Bay Airport rental car and discover Montego Bay and beyond with your own set of wheels. Classique, Island Car Rentals and FlexWays are leading providers you can book with here.
Reserving your vehicle from Montego Bay Airport about three weeks in advance gives you the best shot at securing a great deal.

When to fly to Montego Bay Airport (MBJ)

The quietest month for a flight from Chicago Midway Airport to Montego Bay Airport is September, while December is the most popular. Pick the ideal time to visit Montego Bay based on whether you prefer a more relaxed vibe or a faster pace.
When reserving your flight from Chicago Midway Airport to Montego Bay Airport, think about the kind of weather you enjoy. August is the warmest month in Montego Bay, with temperatures ranging from 25ºC to 31ºC.
Search for cheap tickets from MDW to MBJ in February if you like cooler conditions. Temperatures are at their lowest then, ranging between 22ºC and 28ºC on average.

Explore more of Jamaica

Montego Bay has its own special appeal, but there are so many other parts of Jamaica just waiting to be explored. About 129 kilometres south-east of Montego Bay, a visit to Kingston will keep your itinerary packed. Start with leading attractions like Bob Marley museum, Bob Marley Statue and Blue Mountains.
Spanish Town is another well-known destination in Jamaica and is around 113 kilometres south-east of Montego Bay. No journey is complete without seeing First Iron Bridge In The Caribbean, St. Jago De La Vega Cathedral and People's Museum of Craft & Technology.