Chicago to San Diego (MDW–SAN) — 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–SAN is served by 2 airlines with nonstop service. Southwest Airlines and United Airlines lead the route. The flight covers 1,725 miles in approximately 4h 10m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 46 | 738, 7M8, B38M | 3h56-4h20 | – | – | |
| UA United Airlines | 0 | – | – | Star Alliance | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach San Diego from Chicago
| Metric | MDW→SAN | ORD→SAN | SBN→SAN |
|---|---|---|---|
| Distance from MDW | – | 15 mi | 74 mi |
| Nonstop airlines | 2 | 19 | 1 |
| Weekly flights | 46 | 362 | – |
| Flight time | 4h 10m | 4h 13m | 3h 47m |
| Departure OTP | 68% | – | – |
Travel Essentials
MDW: CDT · SAN: PDT
When it's 6:00 PM in Chicago, it's 4:00 PM in San Diego.
MDW–SAN Quick Facts
Frequently Asked Questions
Flights from MDW to SAN
Chicago Midway International Airport (MDW) and San Diego International Airport (SAN) are connected by nonstop service from Southwest Airlines and United Airlines. With 46 weekly departures, this is a heavily served route.
MDW to SAN Flight Duration and Schedule
Nonstop flight time from MDW to SAN is about 4 hours 10 minutes gate to gate. The route covers a distance of 1,725 miles (2,776 km). There are approximately 46 weekly flights outbound and 49 return, totaling 95 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Kansas City, Phoenix Sky Harbor and Denver. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD), South Bend (SBN) and Milwaukee (MKE).