Question 1

How long is the flight from Oakland to Chicago?

Accepted Answer

The flight from San Francisco Bay Oakland International Airport (OAK) to Chicago Midway International Airport (MDW) covers 2,961 km and takes approximately 3h 47m. Actual duration varies by airline, routing, and wind conditions — check individual flight listings for scheduled times.

Question 2

Which airlines fly from Oakland to Chicago?

Accepted Answer

There are 2 airlines operating the OAK–MDW route. Use the TrackMyWings app to compare schedules, prices, and on-time performance across all carriers on this route.

Question 3

What is the best airline from Oakland to Chicago?

Accepted Answer

The best airline on the OAK–MDW route depends on your priorities — price, on-time performance, cabin experience, or loyalty miles. TrackMyWings tracks real-time on-time data for all 2 carriers on this route so you can make an informed choice.

Question 4

How often do flights operate from Oakland to Chicago?

Accepted Answer

The OAK–MDW route is served by 2 airlines, with combined daily frequency varying by season. Check the TrackMyWings schedule view for live departure listings and to find the next available flight from Oakland to Chicago.

Flight	Airline	Dep Time	Arr Time	Status
FL 6852	AirTran Airways	08:00	14:00	Scheduled
WN 8163	Southwest Airlines	08:00	14:00	Scheduled

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Oakland (OAK) to Chicago (MDW) Flights

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