San Diego to Chicago (SAN–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.
SAN–MDW is served by 2 airlines with nonstop service. Southwest Airlines and Hera Flight lead the route. The flight covers 1,725 miles in approximately 4h. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 48 | 737, 7M8, 7S7, B38M | 3h50-4h05 | – | – | |
| UD Hera Flight | 0 | – | – | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from San Diego
| Metric | SAN→MDW | CLD→MDW | SNA→MDW |
|---|---|---|---|
| Distance from SAN | – | 28 mi | 76 mi |
| Nonstop airlines | 2 | 5 | 9 |
| Weekly flights | 49 | 1 | 1 |
| Flight time | 4h | 3h 27m | 3h 33m |
| Departure OTP | 71% | – | – |
Travel Essentials
SAN: PDT · MDW: CDT
When it's 6:00 PM in San Diego, it's 8:00 PM in Chicago.
SAN–MDW Quick Facts
Frequently Asked Questions
Flights from SAN to MDW
San Diego International Airport (SAN) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines and Hera Flight. With 49 weekly departures, this is a heavily served route.
SAN to MDW Flight Duration and Schedule
Nonstop flight time from SAN to MDW is about 4 hours gate to gate. The route covers a distance of 1,725 miles (2,776 km). There are approximately 49 weekly flights outbound and 46 return, totaling 95 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Phoenix Sky Harbor, Denver and Harry Reid. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Carlsbad (CLD), Santa Ana (SNA) and Palm Springs (PSP).