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
Cheapest roundtrip flight
from€430
Fastest flight
non-stop flights
8x / week
Flight distance
3,566 km
Time difference
none
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Cheap flight offers from Chicago to San Jose Costa Rica

sorted by price and recency
  1. –
    Avianca
    –
    CHI–SJO
    1 stopover
    Avianca
    –
    SJO–CHI
    1 stopover
    €502
  2. –
    Avianca
    –
    CHI–SJO
    1 stopover
    Avianca
    –
    SJO–CHI
    1 stopover
    €452
  3. –
    Avianca
    –
    CHI–SJO
    1 stopover
    Avianca
    –
    SJO–CHI
    1 stopover
    €430
  4. –
    Copa Airlines
    –
    CHI–SJO
    1 stopover
    Copa Airlines
    –
    SJO–CHI
    1 stopover
    €587
  5. –
    Copa Airlines
    –
    CHI–SJO
    1 stopover
    Copa Airlines
    –
    SJO–CHI
    1 stopover
    €1,050
  6. –
    Copa Airlines
    –
    CHI–SJO
    1 stopover
    Copa Airlines
    –
    SJO–CHI
    1 stopover
    €515

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 · 2 of 2
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    No flights could be found for the active filters.
    1. ORDSJO
      1 stopover
      1. JetBlue Airways
    2. ORDSJO
      nonstop
      1. United 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
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