SJC → MDWSan Jose to Chicago

live

Direct flights from San Jose (SJC) to Chicago (MDW): 20 nonstop departures observed each week across 1 airline. 93% of the last 14 tracked flights arrived within 15 minutes of schedule. The median arrival is 13 minutes early. No cancellations were recorded across the 14 tracked flights. The nonstop covers 2,950 km, an estimated 4 hours 17 minutes in the air. Measured by Pro Flight Search from live flight boards at San Jose and Chicago. Updated 5 November 2026 at 03:55 UTC.

Today, SJC → MDW

Wed 4 Nov · local times
  1. 06:00 WN1973Southwest Airlines Left 06:12 +12 Landed 11:49 −21
  2. 11:10 WN576Southwest Airlines Left 11:23 +13 Landed 17:02 −13

Checked SJC board 18:54 · MDW board 21:55

SJC San Jose smooth · +0
MDW Chicago smooth · +12
2,950 km · ~4h 17m est.
dep bank 06:00–23:0020x weekly
Runs reliable · 1 airline · 20x weekly · nonstop
93% on time

of the last 14 tracked SJC → MDW flights arrived within 15 minutes

Median arrival delay is −13 min. 0 of 14 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−13 minacross the last 14 arrivals
Flight time~4h 17mestimated from route distance
Weekly departures20x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 14

The week

scheduled departures · origin local time
06121824
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Southwest Airlines

Each mark is a scheduled departure at its origin-local time, observed operating in the last 7 days. Today is highlighted.

Who flies it

observed on the boards · 7 days
Southwest AirlinesWN93% on time

Flights WN1973 06:00 Tu We · WN4377 06:00 Mo Th Fr · WN576 11:10 Tu We · WN1585 11:15 Tu We

History

operated legs · board outcomes
11-04WN1973dep +12 → arr−21
11-04WN576dep +13 → arr−13
11-03WN1973dep +10 → arr−28
11-03WN576dep +22 → arr−14
11-02WN3854dep +14 → arr−2
11-02WN4230dep +4 → arr−23
11-01WN3854dep +48 → arr+24
11-01WN4230dep +9 → arr−15
10-31WN2557dep +12 → arr+6
10-30WN3824dep +6 → arr−18
10-30WN4377dep +22 → arr+2
10-29WN3824dep +26 → arr+4
10-29WN4377dep +15 → arr−5
10-28WN3824arrived−20

Actual board outcomes rather than schedules, paired departure and arrival per flight and day.

Full board history, day by day →

Airports right now

live boards
SJCSan Jose +0 min smooth 🌤 scattered clouds · NNW 6 kt Full SJC delay board →
MDWChicago +12 min smooth ⛅ mostly cloudy · SW 10 kt Full MDW delay board →

Weather lens

Conditions are tightest at SJC: a 43% chance of a 15+ minute delay. In this weather, the more delayed of the two airports is typically about +8 min. Both figures come from the two airports' delay records in similar weather. See live delays → · Weather risk by airport →

How the San Jose to Chicago route actually runs

Pro Flight Search records official board updates for nonstop SJC to MDW flights through the day: schedules, estimates, gate pushes and actual departures. The verdict above comes from operated flights, so it reflects what this route does rather than what the timetable promises.

Planning around a delay? Live airport delays · Weather delay risk map · Will a delayed flight be cancelled? · Do planes make up time in the air? · How we measure

Cite this data

Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.

Suggested citation

Pro Flight Search: San Jose (SJC) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.

Canonical URL
https://proflightsearch.com/search-flights/SJC-MDW
How we measure this →

SJC to MDW questions

Is SJC–MDW running on time right now?

Mostly on schedule. The arrival side at MDW is the weaker end, route health score 78/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on SJC–MDW?

Operators schedule morning departures around 06:00 and evening departures around 23:00 from SJC. Earlier flights typically land before destination-airport delays accumulate later in the day; check the MDW delay card to confirm conditions when you'd arrive.

How long is the flight from SJC to MDW?

Great-circle distance is 2,950 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 238–283 min gate-to-gate on this route.

How often does SJC–MDW fly?

Southwest Airlines runs the route with about 20 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.