Southwest Airlines flights from Oakland (OAK) to Chicago (MDW)
Find comprehensive Southwest Airlines flight information, schedules, and booking details for direct flights from Oakland (OAK), US to Chicago (MDW), US. Southwest Airlines operates 1-2 flights daily flights on this route.• Flight Duration: 4h 00m - 4h 05m (average flight time)• Distance: 1850 miles (2977 km) (air miles between airports)• Daily Flights: 1-2 flights (scheduled departures per day)
Oakland (OAK)
US
Chicago (MDW)
US
FLIGHT TIME
4h 00m - 4h 05m
FLIGHT DISTANCE
1850 miles (2977 km)
4h 5m - 4h 5m
05:25
05:25
1850 miles (2977 km)
November
1 (Show)
7
Terminal 1 (OAK)
Terminal 1 (MDW)
Southwest Airlines Flight Schedule from Oakland (OAK) to Chicago (MDW)
| Flight | Airline | Departure | Arrival | Aircraft |
|---|---|---|---|---|
WN3808 |  Southwest Airlines | 05:25 | 11:30:00 | Boeing 737MAX 8 Passenger |
Southwest Airlines Monthly Flight Calendar
Loading calendar...
Route Insights
Pricing patterns: November typically offers lower prices due to reduced demand outside peak travel seasons.
Best departure times: Peak departure times are 5:00, offering more flight options and potentially better connections.
Loading price statistics...
Southwest Airlines Policy Highlights
Baggage Policy
Two free checked bags, additional charges apply for excess or overweight baggage.
For detailed baggage policies, visit Southwest Airlines airline page or Southwest Airlines official website.
Check-in Information
Online check-in available 24 hours before departure.
Southwest Airlines Terminal Information
Departure Terminal at Oakland (OAK):
• Southwest Airlines flights from Oakland (OAK) depart from Terminal Terminal 1
• Terminal Terminal 1: Southwest Airlines operates from this terminal
Arrival Terminal at Chicago (MDW):
• Southwest Airlines flights to Chicago (MDW) arrive at Terminal Terminal 1
• Terminal Terminal 1: Southwest Airlines operates from this terminal
Frequently Asked Questions about Southwest Airlines Flights
How many Southwest Airlines flights operate from Oakland (OAK) to Chicago (MDW)?
Southwest Airlines operates 1 flight from Oakland (OAK) to Chicago (MDW).
What city does Chicago (MDW) airport serve?
Chicago (MDW) airport serves Chicago, US.
How long is the Southwest Airlines flight from Oakland (OAK) to Chicago (MDW)?
The flight duration is approximately 4h 00m - 4h 05m.
What is the distance from Oakland (OAK) to Chicago (MDW)?
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 Oakland (OAK)?
Southwest Airlines flights from Oakland (OAK) depart from Terminal Terminal 1.
Which terminal does Southwest Airlines use at Chicago (MDW)?
Southwest Airlines flights to Chicago (MDW) arrive at Terminal Terminal 1.
What is the cheapest month to fly Southwest Airlines from Oakland (OAK) to Chicago (MDW)?
November is typically the cheapest month to fly Southwest Airlines on this route.
What is the average price for a Southwest Airlines flight from Oakland (OAK) to Chicago (MDW)?
The average price for a round-trip Southwest Airlines flight on this route is approximately $574. Prices can vary based on booking time and demand.
How many Southwest Airlines flights operate per week on this route?
Southwest Airlines operates approximately 7 flights per week from Oakland (OAK) to Chicago (MDW).