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.
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 is served by 2 airlines with nonstop service. United Airlines and American Airlines lead the route. The flight covers 2,221 miles in approximately 5h 19m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| UA United Airlines | 1 | B38M | 5h19 | Star Alliance | – | |
| AA American Airlines | 0 | – | – | Oneworld | – |
Weekly Schedule Pattern
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 | 2 | 1 |
| Weekly flights | 1 | 1 |
| Flight time | 5h 19m | 4h 16m |
| Departure OTP | 45% | – |
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) are connected by nonstop service from United Airlines and American Airlines. With 1 weekly departures, this is a regularly served route.
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). There are approximately 1 weekly flights outbound and 1 return, totaling 2 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Miami, Orlando and Hartsfield Jackson Atlanta. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (MDW).