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Cheap Flights from Madison (MSN) to San Jose (SJO)

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      Travellers and cabin class, 1 Adult, Economy

      Compare Madison 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 Madison to San Jose Juan Santamaria

      Looking for a cheap last-minute deal or the best return flight from Madison Airport to San Jose Juan Santamaria Airport? If you want to travel next month, return fares start from $968. Find the lowest prices on one-way and return tickets right here.
      San Jose.$886 per passenger.Departing Fri, 27 Nov, returning Wed, 9 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Fri, 27 Nov, arriving in San Jose Juan Santamaria.Inbound indirect flight with Delta, departs from San Jose Juan Santamaria on Wed, 9 Dec, arriving in Madison.Price includes taxes and charges.From $886, select.
      San Jose.$890 per passenger.Departing Thu, 22 Oct, returning Wed, 28 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Thu, 22 Oct, arriving in San Jose Juan Santamaria.Inbound indirect flight with Delta, departs from San Jose Juan Santamaria on Wed, 28 Oct, arriving in Madison.Price includes taxes and charges.From $890, select.
      San Jose.$914 per passenger.Departing Sat, 30 Jan, returning Sat, 6 Feb.Return flight with United.Outbound indirect flight with United, departs from Madison on Sat, 30 Jan, arriving in San Jose Juan Santamaria.Inbound indirect flight with United, departs from San Jose Juan Santamaria on Sat, 6 Feb, arriving in Madison.Price includes taxes and charges.From $914, select.
      San Jose.$963 per passenger.Departing Fri, 8 Jan, returning Sat, 16 Jan.Return flight with United.Outbound indirect flight with United, departs from Madison on Fri, 8 Jan, arriving in San Jose Juan Santamaria.Inbound indirect flight with United, departs from San Jose Juan Santamaria on Sat, 16 Jan, arriving in Madison.Price includes taxes and charges.From $963, select.
      San Jose.$968 per passenger.Departing Sat, 19 Sep, returning Fri, 25 Sep.Return flight with United.Outbound indirect flight with United, departs from Madison on Sat, 19 Sep, arriving in San Jose Juan Santamaria.Inbound indirect flight with United, departs from San Jose Juan Santamaria on Fri, 25 Sep, arriving in Madison.Price includes taxes and charges.From $968, select.
      San Jose.$1,018 per passenger.Departing Mon, 31 Aug, returning Sun, 6 Sep.Return flight with United.Outbound indirect flight with United, departs from Madison on Mon, 31 Aug, arriving in San Jose Juan Santamaria.Inbound indirect flight with United, departs from San Jose Juan Santamaria on Sun, 6 Sep, arriving in Madison.Price includes taxes and charges.From $1,018, select.
      San Jose.$1,211 per passenger.Departing Sat, 29 May, returning Sat, 5 Jun.Return flight with United.Outbound indirect flight with United, departs from Madison on Sat, 29 May, arriving in San Jose Juan Santamaria.Inbound indirect flight with United, departs from San Jose Juan Santamaria on Sat, 5 Jun, arriving in Madison.Price includes taxes and charges.From $1,211, select.
      San Jose.$2,898 per passenger.Departing Sat, 27 Mar, returning Sat, 3 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Sat, 27 Mar, arriving in San Jose Juan Santamaria.Inbound indirect flight with Delta, departs from San Jose Juan Santamaria on Sat, 3 Apr, arriving in Madison.Price includes taxes and charges.From $2,898, select.

      Find the cheapest month to fly from Madison 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 Madison to San Jose Juan Santamaria flights are currently cheapest in October.
      Aug
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      Sep
      from $968
      Oct
      from $890
      Nov
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      Dec
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      Jan
      from $963
      Feb
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      Mar
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      Apr
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      Madison to San Jose Juan Santamaria: Alternative routes

      Compare routes from Madison 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 $886
      Search flights

      Quepos

      54km from central San Jose
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      Fortuna

      68km from central San Jose
      Search flights

      Madison to San Jose: Flight information

      The things to know before you go.
      Cheapest flight found$886
      Cheapest month to flyNovember

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

      The best price we found for a return flight from Madison to San Jose Juan Santamaria is $886. 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 Madison to San Jose Juan Santamaria. But we found flights with one or more stops from $886.
      As of August 2026, there are no flights flying from Madison to San Jose Juan Santamaria.
      The cheapest month to fly from Madison to San Jose Juan Santamaria is usually November.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to San Jose Juan Santamaria Airport on Friday, 27 November 2026.
      No airlines currently offer direct flights between Madison 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, Delta offers the cheapest flight tickets to San Jose Juan Santamaria.

      Flying from Madison Airport (MSN) to San Jose Juan Santamaria Airport (SJO): what you need to know

      • San Jose's timezone is UTC-6, which is the same as Madison.

      • Arrive at the airport on time so you don't miss your MSN to SJO 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 August, it's best to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead for international flights when you travel during peak periods in general.

      • If you want to include a stop along the way, just deselect 'Direct flights only' when searching for your ticket from Madison Airport to San Jose Juan Santamaria Airport. Here are the most popular stopovers between MSN and SJO:

        • Chicago O'Hare International Airport

        • Atlanta Hartsfield-Jackson Airport

        • Miami International Airport

      Handy information about Madison Airport (MSN)

      • You'll find MSN at 4000 International Lane.

      • When it comes to Madison Airport's on-time performance, 75% of flights meet their scheduled arrival time.

      • Central Madison to Madison Airport is approximately 13 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're ride-sharing, catching a taxi or driving.

      • The journey on public transport usually takes 40 minutes.

      • Booked an early flight from Madison Airport to San Jose Juan Santamaria Airport? Avoid the hassle of rushing to the airport (and sneak in some extra precious sleep) by choosing one of these hotels near MSN:

      Arriving at San Jose Juan Santamaria Airport (SJO)

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

      • From San Jose Juan Santamaria Airport, San Jose is approximately 18 kilometres away. It takes around 25 minutes to drive to the centre.

      • Travelling on public transport takes around 1 hour.

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

      • April is the most popular month for flights from Madison Airport to San Jose Juan Santamaria Airport. For smaller crowds, visit San Jose in March.

      • When booking your flight from Madison Airport to San Jose Juan Santamaria Airport, think about the type of weather you like. March is the warmest month in San Jose, with temperatures ranging from 12ºC (54ºF) to 29ºC (84ºF).

      • For cooler conditions, look for a cheap ticket from MSN to SJO in January. Average temperatures are between 11ºC (52ºF) and 26ºC (79ºF) then.

      Explore more of Costa Rica

      • San Jose has plenty to offer, but there are so many other parts of Costa Rica just waiting to be explored. Around 113 kilometres east of San Jose, a visit to Limon will keep you on the go. Start with leading sights like Veragua Rainforest Park, Playa Bonita and Playa Los Baños.

      Plan smart, explore more

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