Flights operate between Chicago (MDW) and Oakland (OAK).
1 airline operates this route with 1-2 flights daily flights.
Average flight time is 4h 30m - 4h 55m.
Route distance is 1850 miles (2977 km).
Route Distance
1850 miles (2977 km)
Average Duration
4h 30m - 4h 55m
Airlines Operating This Route
Southwest Airlines
Flight Frequency
Daily Flights
1-2 flights
Weekly Flights
7
Typical Departure Time Ranges
Earliest Departure
07:50
Latest Departure
07:50
Route Intelligence Dashboard
Overall Connectivity Score
35
ModerateRoute Diversity
1
Direct Routes
Southwest Airlines serves 1 destination from MDW
Weekly Frequency
7
Weekly Flights
Trend: Stable
Top 1 Most Frequent Routes - Details
| Route | Weekly Flights | Duration | Distance | Reliability |
|---|---|---|---|---|
| MDW → Oakland (OAK) (OAK) | 7/week | 4h 30m - 4h 55m | 1,850 km | Seasonal |
Flight Schedule & Filters
Southwest Airlines flights from Chicago (MDW) to Oakland (OAK)
Southwest Airlines operates scheduled nonstop flights between Chicago (MDW) and Oakland (OAK). Southwest Airlines operates 1-2 flights daily flights on this route.• Flight Duration: 4h 30m - 4h 55m (average flight time)• Distance: 1850 miles (2977 km) (air miles between airports)• Daily Flights: 1-2 flights (scheduled departures per day)
Chicago (MDW)
US
Oakland (OAK)
US
FLIGHT TIME
4h 30m - 4h 55m
FLIGHT DISTANCE
1850 miles (2977 km)
4h 45m - 4h 45m
07:50
07:50
1850 miles (2977 km)
September
1 (Show)
7
Southwest Airlines Terminal Information & Contact
Departure Terminal - Chicago (MDW)
Terminal: 1
Phone: 800-435-9792
Location: 1, Chicago, US
Arrival Terminal - Oakland (OAK)
Terminal: 2
Phone: 800-435-9792
Location: 2, Oakland, US
Southwest Airlines Flight Schedule from Chicago (MDW) to Oakland (OAK)
| Flight | Airline | Departure | Arrival | Aircraft |
|---|---|---|---|---|
WN2376 |  Southwest Airlines | 07:50 | 10:35:00 | Boeing 737MAX 8 Passenger |
Southwest Airlines Monthly Flight Calendar
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Southwest Airlines Terminal Information
Departure Terminal at Chicago (MDW):
• Terminal : Southwest Airlines operates from this terminal
Terminal 1:
• Southwest Airlines Terminal Phone: 800-435-9792
Arrival Terminal at Oakland (OAK):
• Terminal : Southwest Airlines operates from this terminal
Terminal 2:
• Southwest Airlines Terminal Phone: 800-435-9792
Southwest Airlines Contact Information and Customer Services
Southwest Airlines Address
2702 Love Field Dr
Dallas, TX 75235, US
Customer Service Phone
800-435-9792Official Website
southwest.com/Frequently Asked Questions
How many Southwest Airlines flights operate from Chicago (MDW) to Oakland (OAK)?
Southwest Airlines operates 1 flight from Chicago (MDW) to Oakland (OAK).
What city does Oakland (OAK) airport serve?
Oakland (OAK) airport serves Oakland, US.
How long is the Southwest Airlines flight from Chicago (MDW) to Oakland (OAK)?
The flight duration is approximately 4h 30m - 4h 55m.
What is the distance from Chicago (MDW) to Oakland (OAK)?
The distance is 1850 miles (2977 km).
What aircraft does Southwest Airlines use on this route?
Southwest Airlines uses Boeing 737MAX 8 Passenger on this route.
Which terminal does Southwest Airlines use at Chicago (MDW)?
Southwest Airlines flights from Chicago (MDW) depart from Terminal 1. Terminal 1 phone: 800-435-9792.
What is the Southwest Airlines terminal phone number at Chicago (MDW)?
The Southwest Airlines terminal phone number at Chicago (MDW) is 800-435-9792 (Terminal 1).
View all Southwest Airlines flights to Chicago (MDW) →
Popular Southwest Airlines routes from Chicago include multiple destinations.
Route data verified regularly by Triposia Travel Research Team.