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Cheap Flights from Chicago Midway to San Juan

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Chicago Midway to San Juan flight deals

      Find the cheapest month or even day of the year to fly to San Juan

      Book the best San Juan fare with no extra fees

      Flight deals from Chicago Midway to San Juan

      Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to San Juan? If you want to travel next month, return fares start from R 3,615. Find the lowest prices on one-way and return tickets right here.
      San Juan.R 1,802 per passenger.Departing Sat, 3 Oct.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 3 Oct, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 1,802, select.
      San Juan.R 1,805 per passenger.Departing Wed, 30 Sep.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 30 Sep, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 1,805, select.
      San Juan.R 2,122 per passenger.Departing Tue, 10 Nov.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 10 Nov, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 2,122, select.
      San Juan.R 2,528 per passenger.Departing Mon, 31 Aug.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 31 Aug, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 2,528, select.
      San Juan.R 2,761 per passenger.Departing Mon, 15 Feb.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 15 Feb, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 2,761, select.
      San Juan.R 3,349 per passenger.Departing Sat, 5 Dec.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 5 Dec, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 3,349, select.
      San Juan.R 3,430 per passenger.Departing Fri, 22 Jan.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 22 Jan, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 3,430, select.
      San Juan.R 3,648 per passenger.Departing Sat, 28 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 28 Nov, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 3,648, select.
      San Juan.R 3,720 per passenger.Departing Sat, 22 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 22 May, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 3,720, select.
      San Juan.R 4,119 per passenger.Departing Mon, 22 Mar.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 22 Mar, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 4,119, select.
      San Juan.R 4,323 per passenger.Departing Sat, 5 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 5 Dec, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 4,323, select.
      San Juan.R 4,729 per passenger.Departing Fri, 9 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 9 Apr, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 4,729, select.
      San Juan.R 5,407 per passenger.Departing Tue, 1 Jun.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 1 Jun, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 5,407, select.
      San Juan.R 9,785 per passenger.Departing Sat, 13 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 13 Feb, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From R 9,785, select.

      Find the cheapest month to fly from Chicago Midway to San Juan

      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 flights are currently cheapest in October.
      Aug
      from R 2,528
      Sep
      from R 1,805
      Oct
      from R 1,802
      Nov
      from R 2,122
      Dec
      from R 3,349
      Jan
      from R 3,430
      Feb
      from R 2,761
      Mar
      from R 4,119
      Apr
      from R 4,729
      May
      from R 3,720
      Jun
      from R 5,407
      Jul
      Find prices

      Direct flights from Chicago Midway to San Juan

      Southwest Airlines

      Alternative Chicago Midway to San Juan routes

      Looking for the cheapest, fastest or easiest route from Chicago Midway to San Juan? You could fly into the following airports instead.

      San Juan Isla Grande

      1km from central San Juan
      Closest
      Search flights

      San Juan Luis Munoz Marin

      11km from central San Juan
      Cheapest
      from R 1,802
      Search flights

      Roosevelt Roads

      55km from central San Juan
      Search flights

      Ponce

      70km from central San Juan
      from R 3,762
      Search flights

      Vieques

      82km from central San Juan
      Search flights

      Culebra

      85km from central San Juan
      Search flights

      Chicago to San Juan: Flight information

      The things to know before you go.
      Cheapest flight foundR 1,802
      Cheapest month to flyOctober
      Average flight time4 hrs, 42 mins
      Most popular airlineSouthwest Airlines
      Average flights per week2

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

      There are 6 airports in San Juan: San Juan Isla Grande, San Juan Luis Munoz Marin, Roosevelt Roads, Ponce, Vieques, and Culebra.
      The best price we found for a return flight from Chicago Midway to San Juan is R 3,615. 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 42 minutes is the average flight time from Chicago Midway to San Juan.
      Southwest Airlines flies direct from Chicago Midway to San Juan.
      As of August 2026, there are 2 flights per week flying from Chicago Midway to San Juan.
      The cheapest month to fly from Chicago Midway to San Juan is usually September.
      If you're flying from Chicago Midway Airport, the cheapest airport near San Juan is San Juan Luis Munoz Marin – which is 11.3 km away from the centre of San Juan. We've found flights into this airport from R 3,615.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Juan on Wednesday, 23 September 2026.
      Yes – the average flight time is 4 hours and 42 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 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.

      In August, the average temperature is usually around 28°C. August is typically the warmest month in San Juan, when it usually averages around 29°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging 23°C. The rainiest month is September.
      Currently, Southwest Airlines offers the cheapest flight tickets to San Juan.

      Flying from Chicago Midway International Airport (MDW) to San Juan: what you need to know

      • Expect to be travelling for 5 hours 5 minutes. That's the average journey time for a direct flight from Chicago Midway International Airport to San Juan.

      • Chicago Midway International Airport is located in Chicago. Following the UTC-4 timezone, San Juan is two hours ahead of Chicago.

      • For a relaxed start to your MDW to San Juan flight, leave plenty of time to navigate the airport and find your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the general travel rule.

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

      • You can book a direct Chicago Midway International Airport to San Juan ticket. Begin your trip at MDW and arrive at Luis Munoz Marin International Airport (SJU).

      • Southwest Airlines is a popular airline that operates direct flights from Chicago Midway International Airport to San Juan.

      • Consider adding a stopover to potentially unlock a cheaper plane ticket from MDW to San Juan. Simply deselect 'Direct flights only' during your search. Take a detour (and maybe pocket some savings) by stopping at one of these popular airports:

        • Atlanta Hartsfield-Jackson International Airport (ATL)

        • Orlando International Airport (MCO)

        • Nashville International Airport (BNA)

      • Located around 14 kilometres from the centre of Chicago, MDW can be reached in about 25 minutes by car, depending on traffic. Travelling on public transport takes roughly 30 minutes.

      • In search of a hotel close to MDW? If you're boarding an early flight from Chicago Midway International Airport to San Juan, these accommodation options will put you moments from check-in:

      • 76% of flights that leave from Chicago Midway International Airport touch down at their destination on time.

      • MDW is located at 5700 South Cicero.

      How to find the cheapest flights from Chicago Midway International Airport (MDW) to San Juan

      • The best price we've seen for a one-way Chicago Midway International Airport to San Juan flight is R 1,802. The cheapest price for a return flight is R 3,615. Keep in mind fares may change due to availability at the time of booking.

      • Booking early is often the key to securing a cheap flight from MDW to San Juan. Prices tend to rise as demand increases, so the nearer you get to departure, the more it could cost you.

      • The 'Whole month' search tool will show you the cheapest tickets from Chicago Midway International Airport to San Juan throughout the month. It's an easy way to snap up a bargain if your travel dates aren't set in stone.

      • You don't 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 when there's an updated deal for cheap flights from MDW to San Juan.

      • Choose your preferred departure and arrival times, number of stops and airlines with our filters. Then, sort the results for your flight from Chicago Midway International Airport to San Juan by 'Best,' 'Fastest' or 'Cheapest.'

      Airports in San Juan

      Luis Munoz Marin International Airport (SJU)

      • Luis Munoz Marin International Airport (SJU) to central San Juan takes around 20 minutes by car. The centre is roughly 11 kilometres away.

      • It typically takes 1 hour if you're using public transport.

      • Think about booking a hotel close to SJU if you have a late flight from Chicago Midway International Airport to San Juan. Settle into one of these accommodation options and make arrival day easier:

      • To get the lowest price, reserve your vehicle from Luis Munoz Marin International Airport about two weeks ahead of your flight from MDW to San Juan.

      Best time to go to San Juan

      • It's time to pick your travel dates for your flight from Chicago Midway International Airport to San Juan. March is the most popular month to travel to San Juan. If you want a quieter vibe, go in December.

      • When booking your Chicago Midway International Airport to San Juan plane ticket, think about the weather you're most comfortable in. August is the warmest month in San Juan, with temperatures ranging from 24ºC (75ºF) to 32ºC (90ºF).

      • February has average temperatures of between 21ºC (70ºF) and 28ºC (82ºF). Search for a cheap ticket from MDW to San Juan around that time if you like travelling in cooler conditions.

      More about San Juan

      Explore more of Puerto Rico

      • Aguadilla is just one of the many cities in Puerto Rico waiting to be discovered once you've taken in the sights of San Juan. Around 113 kilometres away to the west, its top attractions include Silla Aguadilla, Bridges Surf Beach and Playa Rompe Olas.

      • Isabela is another essential stop in Puerto Rico and is around 105 kilometres west of San Juan. No trip is complete without a visit to Playa montones, Shore Island Beach and Guajataca Forest Reserve.

      Plan the rest of your trip from Chicago to San Juan

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