Direct flights from San Diego to Chicago
25 nonstop flights a week on 1 airline. Zero layovers — one hop from SAN to MDW.
Flight time: about 3h28m nonstop
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 | 6:33a | 3h21m | Fri |
| Southwest SWA4237 | 6:36a | 3h44m | Thu |
| Southwest SWA1184 | 6:42a | 3h17m | Sun |
| Southwest SWA3430 | 6:52a | 3h36m | Sat |
| Southwest SWA770 | 7:01a | 3h31m | Mon |
| Southwest SWA3430 | 7:12a | 3h32m | Wed |
| Southwest SWA770 | 7:18a | 3h23m | Fri |
| Southwest SWA3430 | 7:46a | 3h31m | Tue |
| Southwest SWA4443 | 10:44a | 3h20m | Sat |
| Southwest SWA3137 | 11:34a | 3h30m | Mon |
| Southwest SWA3137 | 11:38a | 3h38m | Fri |
| Southwest SWA4443 | 11:38a | 3h14m | Tue |
| Southwest SWA4443 | 11:50a | 3h21m | Wed |
| Southwest SWA1252 | 12:46p | 3h53m | Thu |
| Southwest SWA770 | 3:47p | 3h29m | Sun |
| Southwest SWA657 | 6:31p | 3h34m | Fri |
| Southwest SWA657 | 6:52p | 3h26m | Mon |
| Southwest SWA2395 | 7:13p | 3h23m | Thu |
| Southwest SWA3431 | 10:46p | 3h34m | Sat |
| Southwest SWA3431 | 10:58p | 3h26m | Mon, Wed, Fri, Sun |
| Southwest SWA1511 | 11:06p | 3h27m | Thu |
| Southwest SWA3431 | 11:23p | 3h23m | Tue |
Southwest
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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 25 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 3h28m 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 3h28m.