COPA has round-trip flights from Chicago (ORD) to San Jose, Costa Rica (SJO) for $221 with a connection. Flights November to April. Weekends available.
Note: Some small OTAs on Skyscanner have this for $197. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.
Change fees are waived on flights purchased before July 31. Airline waiver policy [Link]. Carry-on bag is allowed for free. Seat fees can be avoided by accepting the randomly assigned seat at the gate.
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Click for more details and booking links Cheap Flights: Chicago to San Jose, Costa Rica $197-$221 r/t – COPA