ChicagotoOaklandFlight Time
MDW–OAK · Nonstop
Chicago (Chicago Midway International Airport) to Oakland (Oakland International Airport).
The estimated flight time from Chicago (MDW) to Oakland (OAK) is about 4h 23m, covering 1,840 miles. Southwest Airlines flies the route nonstop with 2-3/day departures, from 01:58 to 21:40 local time.
Plan this routeAt a glance
| Est. flight time | Distance | Route type | Captured freq. | Market |
|---|---|---|---|---|
| ~4h 23m Estimated from great-circle distance — no tracked flights yet. | 1,840 mi | Nonstop | 2-3/day From the current provider sample; confirm live timetables before booking. | Domestic |
Airlines on this route
Nonstop airlines from Chicago to Oakland
Southwest Airlines operates 2-3/day flights from MDW to OAK.
- First departure
- 01:58
- Last departure
- 21:40
- Cadence
- ~every 2 hours
- Scheduled departure times
- 9
| Airline | Captured daily freq. | Aircraft | Departures (local) |
|---|---|---|---|
| Southwest Airlines | 2-3/day | Boeing 737 · Seat map | 01:5810:00 |
Aircraft on this route
Flying the other way?
OAK to MDW flights — 2-3/day on 1 airline →Methodology: airline, aircraft, terminal, and departure-time details come from a full week of published airline schedules for MDW, refreshed on a rolling basis. Frequency uses 17 scheduled departures across 7 observed days; flight time is estimated from flying distance until this route has enough tracked flights for an observed average.
Route FAQ
How long is the flight from Chicago to Oakland?
The estimated flight time from Chicago (MDW) to Oakland (OAK) is about 4h 23m, based on the 1,840-mile flying distance.
How far is Chicago from Oakland?
Chicago (MDW) to Oakland (OAK) is about 1,840 miles by air.
Are there nonstop flights from Chicago to Oakland?
Yes. Southwest Airlines flies nonstop from Chicago (MDW) to Oakland (OAK), with 2-3/day departures.
Which airlines fly from Chicago to Oakland?
Southwest Airlines flies nonstop from Chicago (MDW) to Oakland (OAK).
What aircraft fly from Chicago to Oakland?
The MDW–OAK route is flown with Boeing 737.
Route hubs
Nearby airport options
Near Chicago
- ORD - ChicagoChicago O'Hare International Airport · 15 mi from MDWFlights from ORD
- MKE - MilwaukeeGeneral Mitchell International Airport · 81 mi from MDWFlights from MKE
Near Oakland
- SFO - San FranciscoSan Francisco International Airport · 11 mi from OAKFlights to SFO
- SJC - San JoseNorman Y Mineta San Jose International Airport · 29 mi from OAKFlights to SJC
- SMF - SacramentoSacramento International Airport · 76 mi from OAKFlights to SMF