Cheap Flights from Chicago Midway to San Juan Luis Munoz Marin

Compare Chicago Midway to San Juan Luis Munoz Marin flight deals

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Flight deals from Chicago Midway to San Juan Luis Munoz Marin

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

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

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

Direct flights from Chicago Midway to San Juan Luis Munoz Marin

Chicago to San Juan: Flight information

The things to know before you go.
Cheapest flight foundR 1,612
Cheapest month to flyMay
Average flight time4 hrs, 40 mins
Most popular airlineSouthwest Airlines
Average flights per week2

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

The best price we found for a return flight from Chicago Midway to San Juan Luis Munoz Marin is R 3,223. 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 40 minutes is the average flight time from Chicago Midway to San Juan Luis Munoz Marin.
Southwest Airlines flies direct from Chicago Midway to San Juan Luis Munoz Marin.
As of February 2026, there are 2 flights per week flying from Chicago Midway to San Juan Luis Munoz Marin.
The cheapest month to fly from Chicago Midway to San Juan Luis Munoz Marin is usually May.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Juan Luis Munoz Marin Airport on Friday, 1 May 2026.
Yes – the average flight time is 4 hours and 40 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 San Juan Luis Munoz Marin 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 San Juan 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 San Juan Luis Munoz Marin.

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

  • The average length of a direct flight from Chicago Midway International Airport to Luis Munoz Marin International Airport is 4 hours 40 minutes.

  • San Juan is one hour ahead of Chicago and observes the UTC-4 timezone.

  • Get to the airport on time so you don't miss your MDW to SJU flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.

  • During popular months such as July, you'll want to get to the airport earlier. Plan to arrive two hours before domestic departures and four hours ahead for an international flight when you travel during peak periods in general.

  • Southwest Airlines offers direct flights from Chicago Midway International Airport to Luis Munoz Marin International Airport. Book with this popular airline, then get ready to see the sights in San Juan — and maybe even more of Puerto Rico if you have time.

  • Most passengers choose to fly with Southwest Airlines on this route.

  • With 66.67% of services landing as planned, Southwest Airlines is the most punctual carrier operating MDW to SJU flights.

  • We make it easy to book a flight with a stopover. To see your options for tickets from Chicago Midway International Airport to Luis Munoz Marin International Airport, uncheck 'Direct flights only.' Then, choose a flight with a stop long enough to explore the city of your choice. Popular stopovers between MDW and SJU include:

    • Hartsfield-Jackson Atlanta International Airport

    • Nashville International Airport

    • Orlando International Airport

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

  • At the moment, R 1,600 is the cheapest price we've seen for a one-way Chicago Midway International Airport to Luis Munoz Marin International Airport flight. The best price for a return plane ticket is R 3,223. Remember that fares could change due to availability at the time of booking.

  • Score cheap tickets from MDW to SJU by booking at least six months ahead. Based on our research, that's the sweet spot for picking up a bargain.

  • Schedule your trip for May. That's the cheapest month for flights from Chicago Midway International Airport to Luis Munoz Marin International Airport. If you're flexible with your travel dates, use the 'Whole month' tool to find the cheapest airfare across each month.

  • You won't have to check back in every day to find out if fares have gone down when you create a Price Alert. We'll update you as soon as there's a better deal on cheap flights from MDW to SJU.

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

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • 77.88% of flights that depart Chicago Midway International Airport reach their destination on schedule.

  • Central Chicago to Chicago Midway International Airport is around 19 kilometres. Depending on traffic, it'll take about 20 minutes to get there if you're catching a cab, ride-sharing or driving.

  • The journey on public transport typically takes 45 minutes.

  • Get your break off to a leisurely start by staying near MDW. Whether you have an early flight from Chicago Midway International Airport to Luis Munoz Marin International Airport or just don't like being rushed, these hotels have you covered:

Arriving at Luis Munoz Marin International Airport (SJU)

Getting from Luis Munoz Marin International Airport (SJU) to central San Juan

  • Luis Munoz Marin International Airport is approximately 8 kilometres from the centre of San Juan. Driving there takes about 10 minutes.

  • It'll take around 55 minutes to get there by public transport.

When to fly to Luis Munoz Marin International Airport (SJU)

  • The quietest month for a flight from Chicago Midway International Airport to Luis Munoz Marin International Airport is May, while July is the busiest. Pick the best time to go to San Juan based on whether you prefer a faster pace or a more relaxed vibe.

  • When reserving your flight from Chicago Midway International Airport to Luis Munoz Marin International Airport, consider the kind of weather you enjoy. September is the warmest month in San Juan, with the temperature ranging from 23ºC (73ºF) to 33ºC (91ºF).

  • For cooler conditions, search for a cheap ticket from MDW to SJU in February. Average temperatures are between 20ºC (68ºF) and 28ºC (82ºF) then.

Explore more of Puerto Rico

  • San Juan is easy to fall in love with, but there are so many other parts of Puerto Rico waiting to be explored. Around 10 kilometres west of San Juan, a trip to Bayamon will keep you on the move. Start with popular sights like Plazoleta Ignacio Zorrilla, La Plaza de la Bomba Puertorriqueña, Monumento a los Trovadores and Parque Palm Court.

  • Around 11 kilometres east of San Juan, Carolina is another essential stop in Puerto Rico. Experience the best of this destination with a visit to Isla Verde Beach, Parque de Doble A Roberto Clemente Walker and Drone Zone Track.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.