MDW → SJCChicago to San Jose

live

Direct flights from Chicago (MDW) to San Jose (SJC): 12 nonstop departures observed each week across 1 airline. 92% of the last 13 tracked flights arrived within 15 minutes of schedule. The median arrival is 11 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 Chicago and San Jose. Updated 1 November 2026 at 18:03 UTC.

Today, MDW → SJC

Sun 1 Nov · local times
  1. 10:10 WN3035Southwest Left 10:03 SJC est. 12:36In the air · sched 12:55
  2. 21:15 WN1930Southwest Airlines On scheduleGate B1 ·

Checked MDW board 11:53 · SJC board 10:03

MDW Chicago smooth · +0
SJC San Jose smooth · +0
2,950 km · ~4h 17m est.
dep bank 09:50–21:2012x weekly
Runs reliable · 1 airline · 12x weekly · nonstop
92% on time

of the last 13 tracked MDW → SJC flights arrived within 15 minutes

Median arrival delay is −11 min. 0 of 14 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−11 minacross the last 13 arrivals
Flight time~4h 17mestimated from route distance
Weekly departures12x1 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 AirlinesWN92% on time

Flights WN2990 09:50 Mo Tu We Th Fr · WN1705 10:00 Su · WN1271 20:40 Tu We · WN2080 21:15 Mo Th Fr

History

operated legs · board outcomes
11-01WN3035departed−7
10-31WN2880dep +3 → arr−3
10-30WN2080dep +5 → arr−11
10-30WN2990dep +6 → arr+2
10-29WN2080dep +4 → arr−16
10-29WN2990dep +11 → arr+0
10-28WN1271dep +17 → arr+12
10-28WN2990dep +21 → arr+12
10-27WN1271dep +1 → arr−20
10-27WN2990dep +6 → arr−22
10-26WN2080dep +1 → arr+101
10-26WN2990dep +4 → arr−11
10-25WN1705dep −1 → arr−19
10-25WN1940dep +8 → arr−15

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
MDWChicago +0 min smooth 🌤 overcast · ESE 3 kt Full MDW delay board →
SJCSan Jose +0 min smooth 🌤 mostly cloudy · NNW 4 kt Full SJC 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 Chicago to San Jose route actually runs

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

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

MDW to SJC questions

Is MDW–SJC running on time right now?

Smooth skies ahead. Both endpoints currently score the same, route health score 100/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on MDW–SJC?

Operators schedule morning departures around 09:50 and evening departures around 20:40 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the SJC delay card to confirm conditions when you'd arrive.

How long is the flight from MDW to SJC?

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 MDW–SJC fly?

Southwest Airlines runs the route with about 12 flights a week (sun, mon, tue, wed, thu, fri). Since one carrier owns the route, a single disruption tends to ripple through the day.