Cheap Flights from San Juan Luis Munoz Marin to Chicago Midway

origin
    selected
    destination
      selected
      Travellers and cabin class, 1 Adult, Economy

      Compare San Juan Luis Munoz Marin 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

      Flight deals from San Juan Luis Munoz Marin to Chicago Midway

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

      Find the cheapest month to fly from San Juan Luis Munoz Marin to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Juan Luis Munoz Marin to Chicago Midway flights are currently cheapest in July.

      Direct flights from San Juan Luis Munoz Marin to Chicago Midway

      San Juan Luis Munoz Marin to Chicago Midway: Alternative routes

      Compare routes from San Juan Luis Munoz Marin to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

      San Juan to Chicago: Flight information

      The things to know before you go.
      Cheapest flight foundر.ق.‏ 306
      Cheapest month to flyJuly
      Average flight time5 hrs, 12 mins
      Most popular airlineSouthwest Airlines
      Average flights per week2

      Finding cheap flights from San Juan Luis Munoz Marin to Chicago Midway: Frequently asked questions

      The best price we found for a return flight from San Juan Luis Munoz Marin to Chicago Midway is ر.ق.‏ 619. 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.
      5 hours and 12 minutes is the average flight time from San Juan Luis Munoz Marin to Chicago Midway.
      Southwest Airlines flies direct from San Juan Luis Munoz Marin to Chicago Midway.
      As of June 2025, there are 2 flights per week flying from San Juan Luis Munoz Marin to Chicago Midway.
      The cheapest month to fly from San Juan Luis Munoz Marin to Chicago Midway is usually June 2025.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Juan Luis Munoz Marin Airport to Chicago Midway Airport on Friday, 27 June 2025.
      Yes – the average flight time is 5 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 and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

      Flying from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW): what you need to know

      • Around 5 hours 10 minutes is how long you'll be travelling on a direct flight from Luis Munoz Marin International Airport to Chicago Midway International Airport.

      • Chicago is one hour behind San Juan and follows the UTC-5 timezone.

      • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules to live by. Show up at the airport on time to board your SJU to MDW flight.

      • During popular months like July, it's best to get to the airport even earlier. Plan to arrive two hours before a domestic departure and four hours ahead for international flights whenever you're travelling during peak periods in general.

      • Travelling to Chicago (and then discovering more of United States!) is easy with Southwest Airlines. This popular carrier has direct flights from Luis Munoz Marin International Airport to Chicago Midway International Airport.

      • Most travellers choose to travel with Southwest Airlines on this route.

      • The most punctual carrier that offers SJU to MDW flights is Southwest Airlines. Its services land as planned 66.67% of the time.

      • If you want to break up your flight, just uncheck 'Direct flights only' when searching for your ticket from Luis Munoz Marin International Airport to Chicago Midway International Airport. These are the most popular stopovers between SJU and MDW:

        • Raleigh-Durham International Airport

        • Orlando International Airport

        • Tampa International Airport

      How to find the cheapest flights from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW)

      • The cheapest price we've seen for a one-way Luis Munoz Marin International Airport to Chicago Midway International Airport flight is ر.ق.‏ 306. A round-trip plane ticket right now is ر.ق.‏ 619. Depending on the availability when you book, these fares may change.

      • To secure cheap tickets from SJU to MDW, book your trip six months ahead of your departure date.

      • May is the cheapest month for flights from Luis Munoz Marin International Airport to Chicago Midway International Airport. If you want to travel at a different time of year, the 'Whole month' tool will show you the lowest airfares across every month.

      • Never miss a deal on cheap flights from SJU to MDW by setting up a Price Alert. You'll receive an email or notification on the app when a new low fare is offered.

      • Discover the right flight for you by using the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Luis Munoz Marin International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and journey duration.

      Handy information about Luis Munoz Marin International Airport (SJU)

      • Of the departures from Luis Munoz Marin International Airport, 73.65% touch down on time at their destination.

      • To reach Luis Munoz Marin International Airport from central San Juan, it'll take around 10 minutes if you're planning to drive. This depends on traffic though. It's approximately 8 kilometres from the airport to the city centre.

      • Planning to take public transport? Expect a trip time of around 55 minutes.

      • Taking an early flight from Luis Munoz Marin International Airport to Chicago Midway International Airport? Avoid the hassle of rushing to the airport (and sneak in some extra snooze time) by choosing one of these hotels near SJU:

      Arriving at Chicago Midway International Airport (MDW)

      • Book a hotel close to MDW if you're taking a late Luis Munoz Marin International Airport to Chicago Midway International Airport flight. Choose one of these accommodation options and avoid the hassle of a long transfer:

      • Travel at your own pace with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and find adventure across Chicago and beyond.

      • Reserving your vehicle from Chicago Midway International Airport about four weeks ahead boosts your odds of scoring a great price.

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

      • MDW is located at 5700 South Cicero.

      • Chicago Midway International Airport to the centre of Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

      • Travelling on public transport typically takes 45 minutes.

      When to fly to Chicago Midway International Airport (MDW)

      • July is the most popular month for flights from Luis Munoz Marin International Airport to Chicago Midway International Airport. To skip the crowds, head to Chicago in May.

      • The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Book your flights from Luis Munoz Marin International Airport to Chicago Midway International Airport in this month if you like this kind of weather.

      • If you want cooler conditions, look for a cheap ticket from SJU to MDW in January. Temperatures average between -12ºC and 3ºC then.

      Explore more of United States

      • Columbus is just one of the many places in United States waiting to be discovered once you've taken in the sights of Chicago. Around 451 kilometres away to the south-east, top sights here include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

      • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite 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.