Search flights from Chicago (CHI) to San José (SJO)

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Cheapest flights to San José

The cheapest flights available in the next 60 days – prices are updated regularly

Flying from Chicago to San José: things to know

The most popular route is from Chicago O'Hare International Airport in Chicago to Juan Santamaría International Airport in San José. On average this flight takes 7 hours 58 minutes one-way and costs $855 round-trip.

Most popular route
Chicago O'Hare International Airport (ORD) to Juan Santamaría International Airport (SJO)
Average flight time
7 hours 58 minutes
Average round-trip price
$855
Fly from Chicago to San José
11 airlines

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Airlines that fly from Chicago to San José

Airline options may vary according to recently booked flights and your search terms

  • Spirit Airlines
  • Avianca
  • American Airlines
  • Copa Airlines
  • United Airlines
  • Aeromexico
  • Volaris
  • Southwest Airlines
  • Frontier Airlines
  • VivaAerobus
  • Air Canada

Frequently asked questions

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