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Cheap Flights from Chicago Midway to San Jose Juan Santamaria

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      Travellers and cabin class, 1 Adult, Economy

      Compare Chicago Midway to San Jose Juan Santamaria flight deals

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

      Book the best San Jose Juan Santamaria fare with no extra fees

      Flight deals from Chicago Midway to San Jose Juan Santamaria

      Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to San Jose Juan Santamaria Airport? If you want to travel next month, return fares start from R 6,974. Find the lowest prices on one-way and return tickets right here.
      San Jose.R 2,675 per passenger.Departing Sun, 8 Nov.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 8 Nov, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 2,675, select.
      San Jose.R 2,947 per passenger.Departing Tue, 12 Jan.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 12 Jan, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 2,947, select.
      San Jose.R 2,947 per passenger.Departing Thu, 22 Oct.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 22 Oct, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 2,947, select.
      San Jose.R 3,423 per passenger.Departing Fri, 26 Feb.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 26 Feb, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 3,423, select.
      San Jose.R 3,583 per passenger.Departing Sat, 12 Sep.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 12 Sep, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 3,583, select.
      San Jose.R 3,999 per passenger.Departing Sat, 8 May.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 8 May, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 3,999, select.
      San Jose.R 3,999 per passenger.Departing Sat, 24 Apr.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 24 Apr, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 3,999, select.
      San Jose.R 3,999 per passenger.Departing Tue, 23 Mar.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 23 Mar, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 3,999, select.
      San Jose.R 5,157 per passenger.Departing Fri, 4 Dec.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 4 Dec, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 5,157, select.
      San Jose.R 8,343 per passenger.Departing Thu, 8 Jul.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 8 Jul, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From R 8,343, select.

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

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to San Jose Juan Santamaria flights are currently cheapest in November.
      Sep
      from R 3,583
      Oct
      from R 2,947
      Nov
      from R 2,675
      Dec
      from R 5,157
      Jan
      from R 2,947
      Feb
      from R 3,423
      Mar
      from R 3,999
      Apr
      from R 3,999
      May
      from R 3,999
      Jun
      Find prices
      Jul
      from R 8,343
      Aug
      Find prices

      Chicago Midway to San Jose Juan Santamaria: Alternative routes

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

      San Jose Juan Santamaria

      15km from central San Jose
      ClosestCheapest
      from R 2,675
      Search flights

      Quepos

      54km from central San Jose
      from R 7,421
      Search flights

      Fortuna

      68km from central San Jose
      from R 7,546
      Search flights

      Chicago to San Jose: Flight information

      The things to know before you go.
      Cheapest flight foundR 2,675
      Cheapest month to flyNovember

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

      The best price we found for a return flight from Chicago Midway to San Jose Juan Santamaria is R 6,613. 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.
      Currently, there are no airlines that fly direct from Chicago Midway to San Jose Juan Santamaria. But we found flights with one or more stops from R 6,613.
      As of September 2026, there are no flights flying from Chicago Midway to San Jose Juan Santamaria.
      The cheapest month to fly from Chicago Midway to San Jose Juan Santamaria is usually January.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Jose Juan Santamaria Airport on Wednesday, 20 January 2027.
      No airlines currently offer direct flights between Chicago Midway Airport and San Jose Juan Santamaria Airport. Most routes have one or more stops.
      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 Jose Juan Santamaria 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 Jose is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Southwest Airlines offers the cheapest flight tickets to San Jose Juan Santamaria.

      Travelling from Chicago Midway Airport (MDW) to San Jose Juan Santamaria Airport (SJO): what you need to know

      • Chicago and San Jose share the same timezone, UTC-6.

      • For a stress-free journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to catch your MDW to SJO flight.

      • Flying during a peak month like July? Major public holidays and other popular periods can result in longer lines at security. Play things extra safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

      • We make it a breeze to book a flight with a stopover. To see your options for tickets from Chicago Midway Airport to San Jose Juan Santamaria Airport, deselect 'Direct flights only.' Then, pick a flight offering a stop long enough to visit the city of your choice. Stopovers between MDW and SJO include:

        • Atlanta Hartsfield-Jackson Airport

        • Dallas Fort Worth International Airport

        • Orlando International Airport

      Handy information about Chicago Midway Airport (MDW)

      • MDW's address is 5700 South Cicero.

      • When it comes to the on-time performance of Chicago Midway Airport, data shows 76% of flights complete their journey on time.

      • Central Chicago to Chicago Midway Airport is around 16 kilometres. Depending on traffic, it'll take you about 25 minutes to get there if you're driving, catching a taxi or ride-sharing.

      • Expect a journey time of around 30 minutes on public transport.

      • Get your holiday off to a relaxed start by staying near MDW. Whether you have an early flight from Chicago Midway Airport to San Jose Juan Santamaria Airport or want to avoid feeling rushed, these hotels are ideal:

      Arriving at San Jose Juan Santamaria Airport (SJO)

      Getting from San Jose Juan Santamaria Airport (SJO) to central San Jose

      • San Jose Juan Santamaria Airport to central San Jose has a drive time of around 25 minutes. It's approximately 18 kilometres away.

      • Getting to the centre by public transport takes roughly 1 hour.

      When to fly to San Jose Juan Santamaria Airport (SJO)

      • It's time to plan your trip dates for your flight from Chicago Midway Airport to San Jose Juan Santamaria Airport. April is the most popular month to head to San Jose. If you prefer a quieter vibe, go in March.

      • Lock in your flight from Chicago Midway Airport to San Jose Juan Santamaria Airport for March if you want to go to San Jose during its warmest month. You can expect temperatures of between 12ºC (54ºF) and 29ºC (84ºF).

      • Look for cheap tickets from MDW to SJO in January if you like travelling in cooler conditions. Temperatures are at their lowest around then, ranging between 11ºC (52ºF) and 26ºC (79ºF) on average.

      Explore more of Costa Rica

      • You've visited San Jose, now it's time to explore more of Costa Rica. Journey around 113 kilometres east to Limon to tick off its leading attractions. From Veragua Rainforest Park to Playa Bonita and Playa Los Baños, there's plenty to keep you on the go.

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