Chicago to San José (Alajuela) (ORD–SJO) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Last scheduled nonstop: Aug 2026.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
ORD–SJO had nonstop service from American Airlines and United Airlines, last on the schedule in August 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 2,221 miles in 5h 19m.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| AA American Airlines | 0 | – | – | Oneworld | – | |
| UA United Airlines | 0 | – | – | Star Alliance | – |
Connection Landscape
On-Time Performance
Other ways to reach San José (Alajuela) from Chicago
| Metric | ORD→SJO | MDW→SJO |
|---|---|---|
| Distance from ORD | – | 15 mi |
| Nonstop airlines | – | 1 |
| Weekly flights | – | – |
| Flight time | 5h 19m | 4h 16m |
| Departure OTP | 62% | – |
Travel Essentials
ORD: CDT · SJO: CST
When it's 6:00 PM in Chicago, it's 5:00 PM in San José (Alajuela).
US passport holders enter Costa Rica visa-free for stays up to 180 days. No advance application is needed. Passport must be valid for at least one day beyond the date of entry. A return or onward ticket is required and airlines will check before boarding. Proof of funds (USD 100 per month of stay) may be requested at immigration.
CTA Blue Line runs 24/7 from downtown Loop stations to O'Hare (45 min, $5). Pace buses serve suburbs. Ride-shares cost $35–55 from downtown depending on traffic; add 30+ minutes during rush hour on the Kennedy Expressway.Economy parking lots E/F connect via ATS people mover. Terminal 5 (international) is separate from Terminals 1–3; allow extra time for inter-terminal transfers.
ORD–SJO Quick Facts
Frequently Asked Questions
Flights from ORD to SJO
Chicago O'Hare International Airport (ORD) and Juan Santamaría International Airport (SJO) had nonstop service from American Airlines and United Airlines, last on the schedule in August 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.
ORD to SJO Flight Duration and Schedule
Nonstop flight time from ORD to SJO is about 5 hours 19 minutes gate to gate. The route covers a distance of 2,221 miles (3,575 km).
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Hartsfield Jackson Atlanta, Fort Lauderdale Hollywood and Orlando. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (MDW).