Oakland Airport (OAK) Flights to Chicago Airport (MDW)
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Flights from Oakland International Airport to Midway are in quite low demand and there is only one airliner that operates flights – Southwest Airlines. The official airport code for Oakland International Airport is OAK and for Midway it is MDW.
The price of the flight is dependent on the time of the day you fly and the day of the week with weekends being normally a higher price. If you know the dates you wish to travel then book you flights as soon as you can. The earlier you book your lights the cheaper they will be. You can get saving of up to 50% of you book 2 or 3 months in advance! The ticket prices for most airliners will increase the closer you get the departure date, so as soon as you know the date you will travel you should book your flights.
When arriving at Midway don’t forget to set your watch to the local time!
If you plan on flying to Midway Airport (MDW) from Oakland International Airport (OAK) you can pre-arrange your long or short term parking at Oakland International Airport (OAK).
If you chose to rent a car at Midway Airport (MDW) and need to return it, find the nearest fuel station along your route to Midway Airport (MDW) in order to avoid incurring additional cost when you return your vehicle.
Organise and book your choice of transport to Oakland International Airport (OAK):
- Private Transfers to Oakland International Airport (OAK)
- Buses to Oakland International Airport (OAK)
- Taxis to Oakland International Airport (OAK)
- Train Services to/near Oakland International Airport (OAK)
Ensure your arrival at Midway Airport (MDW) is as smooth as possible by pre-booking your transport - which in many cases will also save you money:
- Car rental at Midway Airport (MDW)
- Private transfers at Midway Airport (MDW)
- Buses from Midway Airport (MDW)
- Taxis from Midway Airport (MDW)
- Train services at or near Midway Airport (MDW)
You can also research and pre-book a hotel near Midway Airport (MDW)
For a full summary of all the airliners that fly from Oakland International Airport to Midway, please see the table below.

Airliner | Mo | Tu | We | Th | Fr | Sa | Su | First Flight | Last Flight | Flights |
---|---|---|---|---|---|---|---|---|---|---|
Southwest Airlines | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 05:55 | 12:05 | VIEW FLIGHTS |
The most direct flights are offered by Southwest Airlines but they only offer 1 flight per week. This flight departs 05:55 and goes by the flight number WN585
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.

Day | Flight Times | Flights | ||||
---|---|---|---|---|---|---|
Monday | 05:55
| VIEW FLIGHTS | ||||
Tuesday | 12:05
| VIEW FLIGHTS | ||||
Wednesday | 12:05
| VIEW FLIGHTS | ||||
Thursday | 05:55
| VIEW FLIGHTS | ||||
Friday | 05:55
| VIEW FLIGHTS | ||||
Saturday | 06:15
| VIEW FLIGHTS | ||||
Sunday | 06:20
| 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.

Route | Stops | Distance | Flying Time |
---|---|---|---|
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.
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Flight Price FAQ - Oakland (OAK) to Chicago (MDW)
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