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Cheap Flights from Montego Bay (MBJ) to Chicago Midway (MDW)

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Montego Bay to Chicago Midway flight deals

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

      Book the best Chicago Midway fare with no extra fees

      £152 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 £239. Find the lowest prices on one-way and return tickets right here.
      Chicago.£152 per passenger.Departing Thu, 5 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Montego Bay on Thu, 5 Nov, arriving in Chicago Midway.Price includes taxes and charges.From £152, select.
      Chicago.£153 per passenger.Departing Sun, 6 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Montego Bay on Sun, 6 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £153, select.
      Chicago.£153 per passenger.Departing Fri, 2 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Montego Bay on Fri, 2 Oct, arriving in Chicago Midway.Price includes taxes and charges.From £153, select.
      Chicago.£229 per passenger.Departing Thu, 6 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montego Bay on Thu, 6 May, arriving in Chicago Midway.Price includes taxes and charges.From £229, select.
      Chicago.£240 per passenger.Departing Sun, 30 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Montego Bay on Sun, 30 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £240, select.
      Chicago.£393 per passenger.Departing Tue, 23 Mar.One-way flight with Flair Airlines.Outbound indirect flight with Flair Airlines, departs from Montego Bay on Tue, 23 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £393, select.
      Chicago.£398 per passenger.Departing Tue, 5 Jan.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Montego Bay on Tue, 5 Jan, arriving in Chicago Midway.Price includes taxes and charges.From £398, select.
      Chicago.£417 per passenger.Departing Tue, 29 Jun.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montego Bay on Tue, 29 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £417, select.
      Chicago.£417 per passenger.Departing Wed, 7 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montego Bay on Wed, 7 Apr, arriving in Chicago Midway.Price includes taxes and charges.From £417, 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 November.
      Aug
      from £240
      Sep
      from £153
      Oct
      from £153
      Nov
      from £152
      Dec
      Find prices
      Jan
      from £398
      Feb
      Find prices
      Mar
      from £393
      Apr
      from £417
      May
      from £229
      Jun
      from £417
      Jul
      Find prices

      Direct flights from Montego Bay to Chicago Midway

      Southwest Airlines

      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.

      Chicago Midway

      9 miles from central Chicago
      Closest
      from £152
      Search flights

      Chicago O'Hare International

      16 miles from central Chicago
      Cheapest
      from £147
      Search flights

      Chicago Rockford

      79 miles from central Chicago
      from £205
      Search flights

      Montego Bay to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found£152
      Cheapest month to flyNovember
      Average flight time4 hrs, 12 mins
      Most popular airlineSouthwest Airlines
      Average flights per week2

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

      The best price we found for a return flight from Montego Bay to Chicago Midway is £239. 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 12 minutes is the average flight time from Montego Bay to Chicago Midway.
      Southwest Airlines flies direct from Montego Bay to Chicago Midway.
      As of August 2026, there are 2 flights per week flying from Montego Bay to Chicago Midway.
      The cheapest month to fly from Montego Bay to Chicago Midway is usually September.
      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 Thursday, 10 September 2026.
      Yes – the average flight time is 4 hours and 12 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 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.

      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.

      Currently, Frontier Airlines offers 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)

      • £152 is currently the lowest price for a one-way Sangster International Airport to Chicago Midway International Airport flight. A return flight starts at £239. 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 2 miles 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 12 miles 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 (59ºF) and 29ºC (84ºF). 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 (10ºF) and 3ºC (37ºF) 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 280 miles 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 160 miles south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are among its highlights.

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      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.