Chicago (MDW) to Oakland (OAK) flights
Southwest Airlines flies nonstop from Chicago Midway International Airport to Oakland San Francisco Bay Airport, with about 13 flights a week in July 2026. The 1,844-mile flight takes about 4h 31m gate to gate.
- Distance
- 1,844 mi · 2,968 km
- Flight time
- 4h 31m
- Airlines
- 1
- Seats filled
- 89%
Airlines flying MDW to OAK
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 13 | Boeing 737 MAX 8, Boeing 737-700 / MAX 7, Boeing 737-800 | 74,607 | 4h 31m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
MDW to OAK flight schedule
3 flight numbers flew this route in August 2026, 2 of them almost daily. The first usually leaves at 10:15am and the last at 8:35pm. 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 2779Southwest Airlines | 10:15am | 12:40pm | 28 | 48% |
| WN 3461Southwest Airlines | 8:25pm | 10:55pm | 4 | n/a |
| WN 1413Southwest Airlines | 8:35pm | 11:05pm | 20 | 35% |
Is MDW to OAK on time?
From September 2025 to August 2026, 61% of 525 flights arrived within 15 minutes of schedule and 1.3% were cancelled. Flights leaving around 11am were the most punctual (86%), those around 4pm the least (42%). Most delay time was caused by late-arriving aircraft (45%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 525 | 61% | 23 min | 1.3% |
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 |
|---|---|---|---|
| 7am to 8am | 52 | 53% | |
| 8am to 9am | 28 | 82% | |
| 9am to 10am | 12 | 75% | |
| 10am to 11am | 146 | 69% | |
| 11am to 12pm | 29 | 86% | |
| 1pm to 2pm | 25 | 71% | |
| 3pm to 4pm | 19 | 74% | |
| 4pm to 5pm | 33 | 42% | |
| 8pm to 9pm | 50 | 50% | |
| 9pm to 10pm | 104 | 47% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 37 | 5,184 | |
| September 2025 | 34 | 4,582 | |
| October 2025 | 35 | 5,462 | |
| November 2025 | 31 | 4,782 | |
| December 2025 | 33 | 5,191 | |
| January 2026 | 32 | 4,059 | |
| February 2026 | 28 | 3,640 | |
| March 2026 | 50 | 7,450 | |
| April 2026 | 53 | 7,734 | |
| May 2026 | 52 | 8,204 | |
| June 2026 | 56 | 8,973 | |
| July 2026 | 57 | 9,346 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.