Flights San Jose → Chicago
SJC → MDW
How long is the flight from San Jose to Chicago?
The flight from San Jose (SJC) to Chicago (MDW) takes 3h 40m on average. That is the median time recorded across 1 scheduled flight on this leg; the actual time varies by a few minutes with wind, routing and take-off queues.
Route overview
The flight route from San Jose to Chicago operates with a high level of punctuality, with 84% of flights arriving on time. On average, the flights experience a delay of 6.1 minutes, and over the course of a year, there are approximately 127 flights along this route serving one of the busiest airports in terms of annual passenger traffic, which sees nearly 19.9 million passengers per year.
Your rights on this US flight (DOT)
US flights have no statutory cash compensation for delays. Under the US DOT rules, if your flight is cancelled or significantly changed and you decline rebooking, you're owed an automatic refund of the unused ticket. The tarmac-delay limit is 3 hours (domestic) / 4 hours (international). Amenities for controllable delays depend on each airline's contract of carriage.
US flight refund rules & checker →General information, not legal advice.
The San Jose (SJC) → Chicago (MDW) route is operated by Southwest Airlines. Across 375 flights monitored in recent months, 76% arrived on time (within 15 min of schedule), with an average delay of 10 minutes. The cancellation rate is 0.27%. FlightGuard's average computed risk is 20.3/100 (medium), updated in real time from weather, ATC delays, strikes, NOTAMs, fuel and flight history. At Chicago the average ATFM delay is 5.5 minutes (main cause: atfm). Departing from San Jose the average ATFM delay is 5.5 minutes.
Heading to Chicago: what to expect in this direction
Flying from San Jose (SJC) to Chicago (MDW) heads east for about 2,950 km, a flight time of roughly 3h 40m.
Departures from San Jose on this leg cluster in the overnight window: about 55% of SJC-MDW flights take off then.
Air-traffic congestion: departing San Jose the average ATFM delay is 5.5 min (atfm); arriving into Chicago it is 5.5 min (atfm).
Across 375 tracked SJC-MDW flights, 76% left on time with an average delay of 10 min and a 0.3% cancellation rate.
Route facts
Flights on this route
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Airline punctuality on this route
| Airline | On-time | Average delay | Cancellations |
|---|---|---|---|
| Southwest Airlines (WN) | 75% | 5 min | 0.3% |
Airlines operating SJC-MDW
Airports
Frequently asked questions about SJC-MDW
The flight from San Jose (SJC) to Chicago (MDW) takes 3h 40m on average. That is the median time recorded across 1 scheduled flight on this leg; the actual time varies by a few minutes with wind, routing and take-off queues.
On the San Jose (SJC) -> Chicago (MDW) route, on-time performance is 76% with an average delay of 10 minutes, based on 375 tracked flights.
The cancellation rate on San Jose-Chicago is 0.27% across 375 monitored flights.
The route is operated by 1 airline: Southwest Airlines.
Enter your flight number on FlightGuard for a real-time analysis based on 9 factors: weather at Chicago, ATC delays, strikes, NOTAMs, fuel, airline punctuality and recent trends.
US flights have no statutory cash compensation for delays. Under US DOT rules, if the airline cancels or significantly changes your flight and you decline rebooking, you're owed an automatic refund of the unused ticket. The tarmac-delay limit is 3 hours (domestic) / 4 hours (international). Meals or hotels for controllable delays depend on each airline's contract of carriage.
