Flights San Diego → Chicago
SAN → MDW
Route overview
The flight route from San Diego to Chicago has a 74% on-time performance rate, with an average delay of 12.2 minutes per flight. Over the past year, this route has seen 271 flights depart from San Diego International Airport, which opened in 1928, connecting to one of the busiest airports in the United States by passenger traffic, handling nearly 19.9 million passengers annually.
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 Diego (SAN) → Chicago (MDW) route is operated by Southwest Airlines. Across 343 flights monitored in recent months, 74% arrived on time (within 15 min of schedule), with an average delay of 12 minutes. The cancellation rate is 2.04%. FlightGuard's average computed risk is 18.3/100 (medium), updated in real time from weather, ATC delays, strikes, NOTAMs, fuel and flight history. At Chicago the average ATFM delay is 2.0 minutes (main cause: atfm). Departing from San Diego the average ATFM delay is 2.0 minutes.
Heading to Chicago: what to expect in this direction
Flying from San Diego (SAN) to Chicago (MDW) heads north-east for about 2,776 km, a flight time of roughly 3h 53m.
Departures from San Diego on this leg cluster in the overnight window: about 64% of SAN-MDW flights take off then.
Air-traffic congestion: departing San Diego the average ATFM delay is 2.0 min (atfm); arriving into Chicago it is 2.0 min (atfm).
Across 343 tracked SAN-MDW flights, 74% left on time with an average delay of 12 min and a 2.0% cancellation rate.
Route facts
Flights on this route
Check the risk of a specific flight.
Flexible on this trip? Compare flights
Airline punctuality on this route
| Airline | On-time | Average delay | Cancellations |
|---|---|---|---|
| Southwest Airlines (WN) | 73% | 6 min | 3.1% |
Airlines operating SAN-MDW
Airports
Frequently asked questions about SAN-MDW
On the San Diego (SAN) -> Chicago (MDW) route, on-time performance is 74% with an average delay of 12 minutes, based on 343 tracked flights.
The cancellation rate on San Diego-Chicago is 2.04% across 343 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.
