Oakland (OAK) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Oakland San Francisco Bay Airport to Chicago Midway International Airport, with about 13 flights a week in July 2026. The 1,844-mile flight takes about 3h 56m gate to gate.
- Distance
- 1,844 mi · 2,968 km
- Flight time
- 3h 56m
- Airlines
- 1
- Seats filled
- 88%
Airlines flying OAK to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 13 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 75,504 | 3h 56m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
OAK to MDW flight schedule
4 flight numbers flew this route in August 2026, 1 of them almost daily. The first usually leaves at 5:20am and the last at 11:55pm. Times are local and can change; check with the airline before you book.
| Flight | Departs | Arrives | Days flown in August 2026 | On time (12 months) |
|---|---|---|---|---|
| WN 2671Southwest Airlines | 5:20am | 11:25am | 12 | 100% |
| WN 4295Southwest Airlines | 5:25am | 11:30am | 4 | n/a |
| WN 3816Southwest Airlines | 10:35am | 4:35pm | 8 | n/a |
| WN 2986Southwest Airlines | 11:55pm | 5:55am | 28 | 79% |
Is OAK to MDW on time?
From September 2025 to August 2026, 85% of 526 flights arrived within 15 minutes of schedule and 0.2% were cancelled. Flights leaving around 6am were the most punctual (93%), those around 11pm the least (78%). Most delay time was caused by late-arriving aircraft (44%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 526 | 85% | 7 min | 0.2% |
Airlines as sold: flights operated by regional partners count under the airline on the ticket. Average delay is across all completed flights, early arrivals counted as zero.
On-time arrivals by departure time
| Scheduled departure | Flights | On time, relative | On time |
|---|---|---|---|
| 5am to 6am | 218 | 90% | |
| 6am to 7am | 30 | 93% | |
| 10am to 11am | 12 | 75% | |
| 11am to 12pm | 62 | 84% | |
| 1pm to 2pm | 14 | 69% | |
| 11pm to 12am | 180 | 78% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 35 | 5,735 | |
| September 2025 | 34 | 5,355 | |
| October 2025 | 35 | 5,449 | |
| November 2025 | 31 | 4,189 | |
| December 2025 | 33 | 4,696 | |
| January 2026 | 32 | 3,975 | |
| February 2026 | 28 | 3,603 | |
| March 2026 | 53 | 7,424 | |
| April 2026 | 53 | 8,141 | |
| May 2026 | 52 | 7,992 | |
| June 2026 | 56 | 9,394 | |
| July 2026 | 58 | 9,551 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.