Chicago to Oakland flights
Direct and connecting flights from Chicago Midway International Airport (MDW) to Metropolitan Oakland International Airport (OAK) — airlines, aircraft types, and the safety record for this route.
Route FAQ
How long does the flight from Chicago to Oakland take?
Flight time from Chicago (MDW) to Oakland (OAK) depends on routing, aircraft type, and whether the flight is direct or connecting. A direct flight typically reflects great-circle distance plus winds, while one-stop options can add several hours depending on the layover airport. The typical block time and frequency we have observed for this route are shown above.
Which airlines fly from Chicago to Oakland?
Airline availability for MDW to OAK changes by season and sometimes week to week as carriers adjust capacity. The airlines and aircraft types observed operating this route, both direct and connecting, are listed below based on real flight-tracking data.
Are there direct flights from Chicago to Oakland?
Direct (nonstop) availability on MDW to OAK varies by date, day of week, and season. Busy city pairs usually have multiple daily nonstops, while thinner routes may only have direct service a few days per week or only during peak seasons.
No fatal or serious occurrence involving any operator on this pair in the last 90 days.
- Southwest Airlines40
| Carrier | Sightings / 90d | Safety events |
|---|---|---|
| Southwest Airlines | 3 sightings | No recorded events |
Planning MDW → OAK
MDW to OAK is a medium-haul route of 2,961 km (1,840 mi). See the return OAK → MDW route.
Alternative airports near Chicago: Chicago (CGX) — 14 km, Chicago (ORD) — 25 km, Gary (GYY) — 34 km.
Alternative airports near Oakland: Hayward (HWD) — 11 km, Alameda (NGZ) — 12 km, San Francisco (SFO) — 18 km.