OaklandtoChicagoFlight Time
OAK–MDW · Nonstop
Oakland (Oakland International Airport) to Chicago (Chicago Midway International Airport).
The estimated flight time from Oakland (OAK) to Chicago (MDW) is about 4h 23m, covering 1,840 miles. Southwest Airlines flies the route nonstop with 2-3/day departures, from 05:05 to 23:55 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 Oakland to Chicago
Southwest Airlines operates 2-3/day flights from OAK to MDW. Departures leave from Terminal 2 at OAK.
- First departure
- 05:05
- Last departure
- 23:55
- Cadence
- 6 departures/day
- Scheduled departure times
- 6
| Airline | Captured daily freq. | Aircraft | Departures (local) |
|---|---|---|---|
| Southwest Airlines | 2-3/day | Boeing 737 · Terminal 2 · Seat map | 05:05 |
Aircraft on this route
Flying the other way?
MDW to OAK 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 OAK, refreshed on a rolling basis. Frequency uses 15 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 Oakland to Chicago?
The estimated flight time from Oakland (OAK) to Chicago (MDW) is about 4h 23m, based on the 1,840-mile flying distance.
How far is Oakland from Chicago?
Oakland (OAK) to Chicago (MDW) is about 1,840 miles by air.
Are there nonstop flights from Oakland to Chicago?
Yes. Southwest Airlines flies nonstop from Oakland (OAK) to Chicago (MDW), with 2-3/day departures.
Which airlines fly from Oakland to Chicago?
Southwest Airlines flies nonstop from Oakland (OAK) to Chicago (MDW).
What aircraft fly from Oakland to Chicago?
The OAK–MDW route is flown with Boeing 737.
Route hubs
Nearby airport options
Near Oakland
- SFO - San FranciscoSan Francisco International Airport · 11 mi from OAKFlights from SFO
- SJC - San JoseNorman Y Mineta San Jose International Airport · 29 mi from OAKFlights from SJC
- SMF - SacramentoSacramento International Airport · 76 mi from OAKFlights from SMF
Near Chicago
- ORD - ChicagoChicago O'Hare International Airport · 15 mi from MDWFlights to ORD
- MKE - MilwaukeeGeneral Mitchell International Airport · 81 mi from MDWFlights to MKE