Oakland Airport (OAK) Flights 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.

We've found the cheapest flights to Chicago

Returns from £297.75

One-way from £168.77

Getting to Oakland International Airport from Midway is very straight forward. There are 3 airliners who all offer direct flights several times a week. 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):

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:

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.

Flights Chart

Airliner	Mo	Tu	We	Th	Fr	Sa	Su	First Flight	Last Flight	Flights
Southwest Airlines	1	1	1	1	1	1	2	05:15	13:10	VIEW FLIGHTS
NetJets	1	0	0	0	0	0	0	17:00	17:00	VIEW FLIGHTS
Flexjet	0	0	1	0	0	0	0	16:30	16:30	VIEW FLIGHTS

The most direct flights are offered by Southwest Airlines but they only offer 1 flight per week. This flight departs 05:15 and goes by the flight number WN2853, WN3123 and 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.

Flights Time In WeekDays

Day

Flight Times

Flights

Monday

05:55

Airline	Flight No
Southwest Airlines	WN585

17:00

Airline	Flight No
NetJets	EJA909

VIEW FLIGHTS

Tuesday

11:00

Airline	Flight No
Southwest Airlines	WN3123

VIEW FLIGHTS

Wednesday

11:00

Airline	Flight No
Southwest Airlines	WN3123