Fly from Chicago to San Jose, Costa Rica for $309 round-trip on American Airlines.
Seen below, we found seats departing ORD on Tuesday, October 6, returning from SJO on Tuesday, October 13. Flights connect via Miami MIA.
Other dates are also available for travel throughout a 330-day period.
For booking info, see our fare details.
Need a room in San Jose? Here's what's available on the above dates on Hotelwatchdog.