MDW → SJCChicago to San Jose

live

Direct flights from Chicago (MDW) to San Jose (SJC): 7 nonstop departures observed each week across 1 airline. 78% of the last 9 operated flights arrived within 15 minutes of schedule. The median arrival is 9 minutes early. No cancellations were recorded across the 9 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 24 October 2026 at 03:05 UTC.

Today, MDW → SJC

Fri 23 Oct · local times
WN2080Southwest AirlinesIn the air, 21 min late

Left MDW at 21:36, 21 min after its 21:15 slot.

Track WN2080 →
  1. 09:50 WN2990Southwest Left 10:26 +36 Landed 12:32 +7
  2. 17:30 1I267NetJets Aviation Sched 17:30Departure not confirmed by the board ·
  3. 18:08 1I867NetJets Aviation Left 17:58 ·
  4. 21:15 WN2080Southwest Airlines Left 21:36 +21 ·

Checked MDW board 22:05 · SJC board 15:03

MDW Chicago smooth · +14
SJC San Jose smooth · +5
2,950 km · ~4h 17m est.
dep bank 09:50–21:207x weekly
Runs mixed · 1 airline · 7x weekly · nonstop
78% on time

of the last 9 operated MDW → SJC flights arrived within 15 minutes

Median arrival delay is −9 min. 0 of 9 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−9 minacross the last 9 operated legs
Flight time~4h 17mestimated from route distance
Weekly departures7x1 direct airline on the leg

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 AirlinesWN75% on time

Flights WN2990 09:50 Mo Tu We Th Fr · WN1705 10:00 Su · WN2483 12:50 Sa · WN1281 19:10 Sa

History

operated legs · board outcomes
10-231I867departed−10
10-23WN2080departed+21
10-23WN2990dep +36 → arr+7
10-22WN2080dep +76 → arr+43
10-22WN2990dep +0 → arr−9
10-21WN1271dep −6 → arr−24
10-21WN2990dep +2 → arr−9
10-20WN1271dep +9 → arr−17
10-20WN2990departed−4

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 +14 min smooth 🌤 mostly cloudy · ESE 4 kt Full MDW delay board →
SJCSan Jose +5 min smooth 🌤 clear · NNW 8 kt Full SJC delay board →

Weather lens

Current conditions put the pressure at MDW and SJC: 44% odds of a 15+ minute delay and around +9 min expected when it bites, measured from this route's own weather-matched delay history. 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. The departure side at MDW is the weaker end, route health score 86/100. 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 19:10 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 14 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.