San Juan to Chicago (SJU–MDW) — 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.
SJU–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 2,059 miles in approximately 4h 50m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 3 | 738, 7M8, 7S7 | 4h50 | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from San Juan
| Metric | SJU→MDW | STT→MDW | EIS→MDW |
|---|---|---|---|
| Distance from SJU | – | 68 mi | 96 mi |
| Nonstop airlines | 1 | 2 | 1 |
| Weekly flights | 3 | 1 | – |
| Flight time | 4h 50m | 4h 50m | 4h 59m |
| Departure OTP | 90% | – | – |
Travel Essentials
SJU: AST · MDW: CDT
When it's 6:00 PM in San Juan, it's 5:00 PM in Chicago.
SJU–MDW Quick Facts
Frequently Asked Questions
Flights from SJU to MDW
Luis Munoz Marin International Airport (SJU) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 3 weekly departures, this is a regularly served route.
SJU to MDW Flight Duration and Schedule
Nonstop flight time from SJU to MDW is about 4 hours 50 minutes gate to gate. The route covers a distance of 2,059 miles (3,314 km). There are approximately 3 weekly flights outbound and 2 return, totaling 5 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Tampa, Punta Cana and Orlando. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Charlotte Amalie (STT) and Beef Island (EIS).