Great-circle route SAN ↔ MDW. Faint dots are other airports, for geographic context. Download this map — free to reuse with a link back to this page.
Frequencies below are per direction, from our most recent schedule sample.
| Direction | Frequency | Days | Airlines |
|---|---|---|---|
| SAN → MDW San Diego to Chicago |
24/wk | Daily | Southwest Airlines |
| MDW → SAN Chicago to San Diego |
24/wk | Daily | Southwest Airlines |
Where a direction shows “—” we track it as an operating nonstop but hold no schedule sample for it — we would rather show nothing than guess.
In 2025, airlines reported 270,108 passengers on 1,986 flights between SAN and MDW — about 740 a day — filling 83% of the 324,798 seats flown. Southwest Airlines Co. carried the most passengers (100%).
Source: US DOT T-100 segment reports — actual airline-reported traffic, scheduled service only, both directions combined. Cargo and charter flights excluded.
Southwest Airlines is the only airline flying the SAN–MDW nonstop.
Recent scheduled departures on this route have used the Boeing 737, Boeing 737-800.
Aircraft assignments change by season and by time of day.
On a long east–west route like this one the two directions do not take the same time. Aircraft flying eastbound ride the mid-latitude jet stream and typically arrive earlier than the westbound leg, which flies into it. The difference is commonly 30 to 90 minutes on transatlantic and transpacific flights, and it varies by season. The estimate above does not model wind — treat it as a midpoint and check the airline's own timetable for the block time on your date.
The distance between San Diego International Airport and Chicago Midway International Airport is 1,725 miles, or 2,776 kilometres.
| Great-circle distance | 1,725 mi |
| Kilometres | 2,776 km |
| Nautical miles | 1,499 nmi |
Measured airport to airport. The actual track is longer — aircraft follow airways, avoid restricted airspace and route around weather.
Yes. Southwest Airlines flies the route nonstop, with about 48 departures a week across both directions. The route is in our live nonstop dataset, last seeded 2026-07-07.
About 3h 56m in the air. That is a great-circle estimate from the 1,725-mile distance, not a scheduled block time — an airline's published time will differ by roughly 15 to 45 minutes depending on routing, winds and taxi.
About 24 a week from San Diego to Chicago and 24 a week from Chicago to San Diego, from our most recent schedule sample.
Southwest Airlines.
In 2025, airlines reported 270,108 passengers on 1,986 scheduled flights between SAN and MDW — about 740 a day — filling 83% of the seats flown. Source: US DOT T-100 segment reports, both directions combined.
Recent scheduled departures have used the Boeing 737, Boeing 737-800. Assignments change by season and by time of day.
