Flights Chicago → Oakland
MDW → OAK
Route overview
The flight route from Chicago to Oakland has a 58% on-time performance rate, with an average delay of 24 minutes. The destination airport in Oakland, which opened in 1927, serves over eleven 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 Chicago (MDW) → Oakland (OAK) route is operated by Southwest Airlines. Across 173 flights monitored in recent months, 62% arrived on time (within 15 min of schedule), with an average delay of 21 minutes. The cancellation rate is 4.05%. FlightGuard's average computed risk is 21.4/100 (medium), updated in real time from weather, ATC delays, strikes, NOTAMs, fuel and flight history. At Oakland the average ATFM delay is 1.4 minutes (main cause: airspace/NAS (BTS)). Departing from Chicago the average ATFM delay is 2.0 minutes.
Heading to Oakland: what to expect in this direction
Flying from Chicago (MDW) to Oakland (OAK) heads west for about 2,961 km, a flight time of roughly 4h 7m.
Departures from Chicago on this leg cluster in the overnight window: about 57% of MDW-OAK flights take off then.
Air-traffic congestion: departing Chicago the average ATFM delay is 2.0 min (atfm); arriving into Oakland it is 1.4 min (airspace/NAS (BTS)).
Across 173 tracked MDW-OAK flights, 62% left on time with an average delay of 21 min and a 4.0% 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) | 73% | 6 min | 3.1% |
Airlines operating MDW-OAK
Airports
Frequently asked questions about MDW-OAK
On the Chicago (MDW) -> Oakland (OAK) route, on-time performance is 62% with an average delay of 21 minutes, based on 173 tracked flights.
The cancellation rate on Chicago-Oakland is 4.05% across 173 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 Oakland, 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.
