Flight Routes from Chicago to San Jose, Costa Rica

Compare cheap outbound and return flights from Chicago (CHI) to San Jose, Costa Rica (SJO) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
8x / week
Flight distance
3,566 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

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.

offers
Active filtersnone
Matching outbound flightsCHI–SJO · 6 of 6
fromto
dep.arr.
durationstopovers
  1. September 20 – 26, 2026
  2. Sep 27 – Oct 3, 2026
  3. October 4 – 10, 2026
    1. ORDSJO
      1 stopover
      1. JetBlue Airways
    2. ORDSJO
      1 stopover
      1. Copa Airlines
    3. ORDSJO
      1 stopover
      1. Copa Airlines
    4. ORDSJO
      1 stopover
      1. Copa Airlines
    5. ORDSJO
      1 stopover
      1. Copa Airlines
    6. 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

      Discover more flights around Chicago and San Jose, Costa Rica

      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
      Flight destinations with a similar price