Flights from Oakland Airport OAK to Chicago Airport MDW

Q: How long does the flight from Oakland to Chicago to take?

The flight from Oakland to Chicago takes4 Hours 18 Minutes.

If it is your first time travelling to Midway then check out the airliners Solairus Aviation and Southwest Airlines. These airliners all offer direct flights that depart from Oakland International Airport, so you will find flying to Midway is quite easy. The flight time is approximately 4 Hours 18 Minutes.

The exact cost of the flight we vary quite significantly base on the dates you travel, the time of day you will depart and how long in advance you pre book the flights. The cheapest flights available will generally be mid week or late in the evening, so if you are on a budget then these are the flight times you should consider. Alternatively, you could book well in advance and you flight could be up to 50% cheaper, especially with budget airliners. 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 are planning a trip to Midway Airport from Oakland International Airport you can pre-arrange short or long term parking at Oakland International Airport.

If you are renting a car at Midway Airport it is recommended to fill up the fuel tank before returning the vehicle at the nearest fuel station to Midway Airport in order to avoid incurring additional costs. *Please check your rental agreement to understand the fuel policy for your vehicle.

We suggest pre-booking your transport to Oakland International Airport. The following options are available:

Ensure your arrival at Midway Airport is as stress-free as possible by pre-booking your onwards transport - booking early may also save you money:

Find hotels close to Midway Airport many hotels offer airport transfers directly from the airport to your hotel.

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	1	1	1	1	1	1	1	05:40	10:50	VIEW FLIGHTS
Solairus Aviation	0	0	1	0	0	0	0	15:00	15:00	VIEW FLIGHTS

Flights from Oakland International Airport to Midway are very limited. Only Southwest Airlines operate flights, of which there is only 1 per week. The time of the departure for this flight is 05:40

You can find the latest flight availability and prices from Southwest Airlines at www.southwest.com/?ref=southwestairlines.com. You can also book direct and get their latest discounts.

Flight times for the route are summarised in the table below. These time were correct at the time of writing, but please be aware that times may vary from time to time so please check their website for exact times and the dates you wish to fly.

Flights Time In WeekDays

Day

Flight Times

Flights

Monday

05:40

Airline	Flight No
Southwest Airlines	WN1665

VIEW FLIGHTS

Tuesday

10:50

Airline	Flight No
Southwest Airlines	WN547

VIEW FLIGHTS

Wednesday

10:50

Airline	Flight No
Southwest Airlines	WN547