Chicago to San José (Alajuela) (MDW–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.
MDW–SJO has no scheduled airline service; it is flown by charter / private operators. 1-stop connecting options are also available.
Connection Landscape
On-Time Performance
Other ways to reach San José (Alajuela) from Chicago
| Metric | MDW→SJO | ORD→SJO |
|---|---|---|
| Distance from MDW | – | 15 mi |
| Nonstop airlines | – | 3 |
| Weekly flights | ~1 | 1 |
| Flight time | 4h 16m | 5h 19m |
| Departure OTP | 40% | – |
Travel Essentials
MDW: 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.
MDW–SJO Quick Facts
Frequently Asked Questions
Flights from MDW to SJO
Chicago Midway International Airport (MDW) and Juan Santamaría International Airport (SJO) are connected through multiple connecting hub airports.
MDW to SJO Flight Duration and Schedule
Nonstop flight time from MDW to SJO is about 4 hours 16 minutes gate to gate. The route covers a distance of 2,207 miles (3,552 km).
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Fort Lauderdale Hollywood, Miami and William P. Hobby. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).