Flights Oakland → Chicago
OAK → MDW
How long is the flight from Oakland to Chicago?
The flight from Oakland (OAK) to Chicago (MDW) takes about 4h 7m. This is an estimate based on the distance between the two airports: the real time depends on the aircraft, wind and any stops.
Route overview
This flight route operates from Oakland, California, to Chicago, using Boeing 737-800 aircraft and has an on-time performance rate of 83%, with a mean delay of 6.2 minutes per flight. Over the past year, it has recorded 136 total flights, connecting passengers to one of the busiest airports in terms of annual passenger traffic at nearly 19.9 million people.
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 Oakland (OAK) → Chicago (MDW) route is operated by Southwest Airlines. Across 348 flights monitored in recent months, 79% arrived on time (within 15 min of schedule), with an average delay of 10 minutes. The cancellation rate is 1.44%. FlightGuard's average computed risk is 15/100 (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 Oakland the average ATFM delay is 5.5 minutes.
Heading to Chicago: what to expect in this direction
Flying from Oakland (OAK) to Chicago (MDW) heads east for about 2,961 km, a flight time of roughly 4h 7m.
Departures from Oakland on this leg cluster in the midday window: about 45% of OAK-MDW flights take off then.
Air-traffic congestion: departing Oakland the average ATFM delay is 5.5 min (atfm); arriving into Chicago it is 5.5 min (atfm).
Across 348 tracked OAK-MDW flights, 79% left on time with an average delay of 10 min and a 1.4% 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 OAK-MDW
Airports
Frequently asked questions about OAK-MDW
The flight from Oakland (OAK) to Chicago (MDW) takes about 4h 7m. This is an estimate based on the distance between the two airports: the real time depends on the aircraft, wind and any stops.
On the Oakland (OAK) -> Chicago (MDW) route, on-time performance is 79% with an average delay of 10 minutes, based on 348 tracked flights.
The cancellation rate on Oakland-Chicago is 1.44% across 348 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.
