Direct flights from San Diego to Chicago
23 nonstop flights a week on 1 airline. Zero layovers — one hop from SAN to MDW.
Flight time: about 3h35m nonstop
Flying back? Chicago Midway → San Diego · 24 nonstop flights a week
Which days does it fly?
When does it fly?
Departure times in San Diego local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA4237 | 6:15a | 3h38m | Mon, Thu, Fri |
| Southwest SWA2772 | 6:15a | 3h34m | Tue–Wed |
| Southwest SWA1785 | 6:30a | 3h35m | Sat |
| Southwest SWA3370 | 11:15a | 3h36m | Tue–Wed |
| Southwest SWA1252 | 11:55a | 3h28m | Mon, Thu, Fri |
| Southwest SWA1301 | 12:25p | 3h38m | Sun |
| Southwest SWA3026 | 12:55p | 3h17m | Sat |
| Southwest SWA2395 | 6:45p | 3h33m | Mon, Thu, Fri |
| Southwest SWA2337 | 10:40p | 3h35m | Sat |
| Southwest SWA1565 | 10:40p | 3h36m | Sun |
| Southwest SWA1511 | 10:40p | 3h40m | Mon–Fri |
Southwest
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Other airports near San Diego with nonstops to Chicago
| Airport | Distance | Flights / wk |
|---|---|---|
| LGB — Long BeachSouthwest | 93 mi | 7 |
| ONT — OntarioSouthwest | 94 mi | 7 |
| LAX — Los AngelesSouthwest | 109 mi | 25 |
| BUR — BurbankSouthwest | 122 mi | 7 |
The route
One hop: SAN → MDWDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from San Diego (SAN) to Chicago (MDW)
San Diego International Airport (SAN) has 23 nonstop flights a week to Chicago (MDW), operated by Southwest. No layovers, no connections — one hop out of SAN and you're there.
This route flies every day of the week, so any travel day works. Route data updated October 2026 from observed departures.
Route data updated October 2026 from observed flight departures. Schedules change — always confirm with the airline before booking.
How long is the flight from San Diego to Chicago?
The nonstop flight from San Diego (SAN) to Chicago (MDW) takes about 3h35m in the air, based on recently observed nonstop departures.
How long does it take to drive from San Diego to Chicago?
Driving from San Diego to Chicago takes about 30h 20m behind the wheel — roughly 2,080 miles, or about 3 days of real driving. The nonstop flight takes about 3h35m.
Is there a nonstop return flight from Chicago to San Diego?
Yes — 24 nonstop flights a week from Chicago Midway (MDW) back to San Diego (SAN) on Southwest, based on recently observed departures.