Oakland to Chicago Flights OAK → MDW

San Francisco Bay Oakland International Airport → Chicago Midway International Airport

🇺🇸 Oakland, US → 🇺🇸 Chicago, US

The Oakland to Chicago route connects San Francisco Bay Oakland International Airport (OAK) in US with Chicago Midway International Airport (MDW) in US. This medium-haul flight covers approximately 1842 miles (2964 km) with a typical flight time of 3h 36m. This route is served by 2 airlines: Southwest, NetJets Aviation. AirportRoutes has tracked 4 daily flights on this route.

Departure Airport

San Francisco Bay Oakland International Airport

ICAO Code:
KOAK
IATA Code:
OAK
City:
🇺🇸 Oakland
Country:
US
Elevation:
9 ft

Destination Airport

Chicago Midway International Airport

ICAO Code:
KMDW
IATA Code:
MDW
City:
🇺🇸 Chicago
Country:
US
Elevation:
620 ft

2

Operators

4

Daily Flights

1842

Miles

3h 36m

Flight Duration

Route Map

Operating Airlines

Airline ICAO IATA
Southwest SWA WN
NetJets Aviation EJA 1I

Flight Schedule Pattern

Day Flights Observed Frequency Activity
Monday 9 18%
Tuesday 2 4%
Wednesday 6 12%
Thursday 6 12%
Friday 11 22%
Saturday 4 8%
Sunday 13 25%

Pattern Analysis

4 Daily Flights:
SWA4248 SWA2363 SWA199 EJA274
Data Points: 51
API observations used to build this analysis
Weekdays: 34 flights
Weekend: 17 flights
Business Route More active on weekdays

All Flight Routes

2 Routes
Note: This table shows aggregated route data by airline. Each airline may operate multiple daily flights at different times. See the "Spotted Departure Times" section below for all observed departure times.
Airline Flight Numbers Aircraft Type Typical Time Days Active Last Seen Status
EJA274 E545 15:00 3:00 PM (Representative)
M T W T F S S
Dec 11, 2025 Active
Southwest
SWA / WN
SWA4248 SWA2363 SWA199 B738 11:10 11:10 AM (Representative)
M T W T F S S
Feb 4, 2026 Active
Total Routes: 2
Active Routes: 2
Unique Airlines: 2
Aircraft Types: 2

Spotted Departure Times

Departure Time Operator ICAO IATA
11:10 11:10 AM Southwest SWA WN
15:00 3:00 PM NetJets Aviation EJA 1I

Time Information

Times are shown in the departure airport's local timezone (KOAK - America/Los_Angeles).

Total Departure Times: 2
Time Range:
11:10 - 15:00
These are typical departure times observed from actual flights. Times may vary by season and schedule changes.