Flight Routes from Chicago to San Jose, Costa Rica

Trip type

Our cheapest offers for flights from Chicago to San Jose, Costa Rica

Here you can compare cheap flights from Chicago (CHI) to San Jose, Costa Rica (SJO) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to San Jose, Costa Rica. Prices and availability may change at any time.

Flight schedule from Chicago (CHI) to San Jose, Costa Rica (SJO)

Select a travel date in the flight schedule for the route from Chicago (CHI) to San Jose, Costa Rica (SJO) and compare affordable flight deals.

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Matching outbound flights5 of 5
fromto
dep.arr.
durationstopovers
  1. August 9 – 15, 2026
  2. August 16 – 22, 2026
  3. August 23 – 29, 2026
    1. ORDSJO
      1 stopover
      1. American Airlines
    2. ORDSJO
      1 stopover
      1. JetBlue Airways
    3. ORDSJO
      nonstop
      1. United Airlines
    4. ORDSJO
      1 stopover
      1. Copa Airlines
    5. ORDSJO
      1 stopover
      1. Copa Airlines

      Tips and tricks to help you find cheap flights from Chicago to San Jose, Costa Rica

      Favorite airline: Copa
      Flight tickets on the route Chicago – San Jose, Costa Rica are most frequently booked with Copa.
      Copa
      26 %
      Spirit Airlines
      23 %
      United Airlines
      19 %
      Direct flights are more expensive
      On this route, direct flights are $173.00 more expensive than flights with a stopover.
      non stop flight
      1 stop
      2 stops
      06h 45min
      25h 29min
      15h 50min
      $452
      $279
      $352
      Favourite connection: via Panama City
      35 % of booked tickets on this route are for flights with a transfer in Panama City.
      Route
      bookings
      1 stopover Panama City-Tocumen International
      30h 15min, from $412
      35 %
      1 stopover Houston - George Bush Intercontinental Airport, TX
      13h 56min, from $311
      23 %
      1 stopover Mexico City-Juarez International
      17h 13min, from $634
      12 %

      Important flight information

      Flight information: Chicago - San Jose, Costa Rica

      Roundtrip from $508.80
      Flight duration min. 05:12
      Return flight duration min. 05:37
      Distance 3566 km
      Flights per week 8
      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport San Jose, Costa Rica (SJO)
      Destination country Flights to Costa Rica
      Departure airport - Destination country Chicago-IL, all airports - Costa Rica
      Alternative flights to San Jose, Costa Rica
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