San José (Alajuela) to Chicago (SJO–MDW) — Airlines, Schedules & Connections

SJO Airport Page →
airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 22 1-stop flights
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

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.

✦ 1-Stop connections via 10 hubs
MCO Orlando 6h 45m B6F9Q6 → WNWWI Orlando (MCO) to Chicago flights
HOU Houston 7h 20m WN → WN Houston (HOU) to Chicago flights
MIA Miami 7h 27m AAACAV → EJAWN Miami (MIA) to Chicago flights
BWI Baltimore 7h 35m WN → WN Baltimore (BWI) to Chicago flights
ATL Atlanta 7h 35m AFDLKL → AFAMDL Atlanta (ATL) to Chicago flights
DFW Dallas-Fort Worth 7h 38m AA → F9Y4 Dallas-Fort Worth (DFW) to Chicago flights
FLL Fort Lauderdale 7h 38m B6NK → EJAWN Fort Lauderdale (FLL) to Chicago flights
DEN Denver 8h 46m UAWN → WN Denver (DEN) to Chicago flights
IAH Houston 10h 23m ACPWRUA → UA Houston (IAH) to Chicago flights
LAX Los Angeles 12h 40m ASUA → WN Los Angeles (LAX) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
San José (Alajuela) to Chicago
Connecting service available through multiple hubs.
+1h ahead

While no nonstop service exists between SJO and MDW, 1-stop connecting options are available.

Also explore SJO Routes MDW Routes SJO Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to San José (Alajuela) flights
Connections

Connection Landscape

1-stop and 2-stop options for SJO to MDW.
1-STOP
One-Stop Connections
22
Hubs
~6h
Fastest
~25h
Longest
MCO ~6h 45m TPA ~7h 7m AUS ~7h 20m HOU ~7h 20m MIA ~7h 27m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,291
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
SJO → MDW
67%
Moderate delays possible. Allow buffer time.
Arriving
67%
Return
MDW → SJO
43%
Frequent delays expected. Consider flexible booking.
Departing
43%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Chicago from San José (Alajuela)

Nearby airports with service to Chicago Midway International Airport.
Metric SJO→MDW LIR→MDW
Distance from SJO – 100 mi
Nonstop airlines – 1
Weekly flights – –
Liberia (LIR) to Chicago flights
Airports within 200 miles of SJO with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+1h
Chicago is 1 hour ahead of San José (Alajuela).
SJO: CST · MDW: CDT

When it's 6:00 PM in San José (Alajuela), it's 7:00 PM in Chicago.
Facts

SJO–MDW Quick Facts

Key statistics for the San José (Alajuela) to Chicago route.
Route details
Time difference+1 hour
Airlines (nonstop)0
1-stop connectionsAvailable
Origin: SJO
Full nameJuan Santamaría International Airport
IATA / ICAOSJO / MROC
TimezoneAmerica/Costa_Rica
Passengers/yr7.5M
Elevation3,021 ft / 921 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about SJO to MDW flights.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Orlando, William P. Hobby and Miami.
Chicago is 1 hour ahead of San José (Alajuela).
Yes, return flights from MDW to SJO are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include LIR. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Orlando, William P. Hobby and Miami. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Liberia (LIR).