Oakland Airport (OAK) Flights to Chicago Airport (MDW)

For a full summary of all the airliners that fly from Oakland International Airport to Midway, please see the table below.

Flights Chart

Airliner	Mo	Tu	We	Th	Fr	Sa	Su	First Flight	Last Flight	Flights
Southwest Airlines	2	2	2	2	2	1	2	05:05	23:55	VIEW FLIGHTS
Charter Airlines	0	0	0	0	0	1	0			VIEW FLIGHTS

The most direct flights are offered by Southwest Airlines but they only offer 1 flight per week. This flight departs 05:05 and goes by the flight number WN2211, WN2744, WN2761 and WN3059

If you wish to book your flight with Southwest Airlines then we advise you book direct from their website at www.southwest.com/?ref=southwestairlines.com. The best discounts can only be obtained from their website.

The flight time for the selected route vary based on the month you will travel, but below we has summarised the most common times they will fly. We recommend you only take these times as guidance and check with appropriate airline for the exact times for the date you depart.

Flights Time In WeekDays

Day	Flight Times	Flights
Monday	05:10 Airline Flight  No Southwest Airlines WN2744 23:55 Airline Flight  No Southwest Airlines WN3059	VIEW FLIGHTS
Tuesday	05:55 Airline Flight  No Southwest Airlines WN2761 23:55 Airline Flight  No Southwest Airlines WN3059	VIEW FLIGHTS
Wednesday	05:55 Airline Flight  No Southwest Airlines WN2761 23:55 Airline Flight  No Southwest Airlines WN3059	VIEW FLIGHTS
Thursday	05:10 Airline Flight  No Southwest Airlines WN2744 23:55 Airline Flight  No Southwest Airlines WN3059	VIEW FLIGHTS
Friday	05:10 Airline Flight  No Southwest Airlines WN2744 23:55 Airline Flight  No Southwest Airlines WN3059	VIEW FLIGHTS
Saturday	10:00 Airline Flight  No Charter Airlines RKJ750 23:55 Airline Flight  No Southwest Airlines WN3059	VIEW FLIGHTS
Sunday	05:05 Airline Flight  No Southwest Airlines WN2211 06:00 Airline Flight  No Southwest Airlines WN3059	VIEW FLIGHTS

If you are flexible on the airport you depart from, then there are other airports that offer direct flights to Midway. You can see full details of these below.

Alternative Direct Routes

Route	Stops	Distance	Flying Time
Monterey to Chicago Midway	0		4 Hours 18 Minutes
Mountain View to Chicago Midway	0		4 Hours 17 Minutes
Reno to Chicago Midway	0		3 Hours 59 Minutes
San Francisco to Chicago Midway	0		4 Hours 19 Minutes
Mineta San Jose to Chicago Midway	0		4 Hours 17 Minutes
Sacramento to Chicago Midway	0		4 Hours 11 Minutes

Whilst you will find a bureau de change at Midway, we recommend you change some money before you depart if you don’t have the local currency. The exchange rates within any airport are not very favorable, so exchanging money before hand is a good idea.