Flights from Oakland Airport (OAK) to Chicago Midway Airport 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 NetJets 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. When travelling from Oakland International Airport you will cover about 1,840 miles before you reach Midway. This journey will take 4 Hours 18 Minutes.

The cost of flights varies on the time and day you fly. If you are on a tight budget then you should avoid flying at peak hours as the prices are more expensive. The cheapest flights are in the evenings and in mid week. We advise all our viewers to book well in advance. This way you will get the low priced tickets available.

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 rented a vehicle at Midway Airport and have to return it with a full tank of fuel, avoid excess fees by refilling at the nearest fuel station to Midway Airport.

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

Pre-booking your transportation requirements at Midway Airport can save a lot of time, hassle and money when arriving at the airport. Research and book your preferred choice of ground transportation at Midway Airport:

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

The table below displays the numbers of daily flights from Oakland International Airport (OAK) to Midway (MDW) and the relevant airlines that fly.

Flights Chart

Airliner	Mo	Tu	We	Th	Fr	Sa	Su	First Flight	Last Flight	Flights
Southwest Airlines	2	3	2	3	2	3	2	00:05	18:50	VIEW FLIGHTS
NetJets	0	1	0	0	0	0	0	15:36	15:36	VIEW FLIGHTS

Southwest Airlines offer the highest number of flights for this route with departures times between 00:05 and 18:50.

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

12:10

Airline	Flight No
Southwest Airlines	WN3788

18:50

Airline	Flight No
Southwest Airlines	WN801

VIEW FLIGHTS

Tuesday

00:50

Airline	Flight No
Southwest Airlines	WN801

06:25

Airline	Flight No
Southwest Airlines	WN1183

15:36

Airline	Flight No
NetJets	EJA819

18:05

Airline	Flight No
Southwest Airlines	WN2643

VIEW FLIGHTS

Wednesday

00:05

Airline	Flight No
Southwest Airlines	WN2643

06:25

Airline	Flight No
Southwest Airlines	WN1183

VIEW FLIGHTS

Thursday

00:05

Airline	Flight No
Southwest Airlines	WN2643

05:55

Airline	Flight No
Southwest Airlines	WN3788

18:50

Airline	Flight No
Southwest Airlines	WN801

VIEW FLIGHTS

Friday

00:50

Airline	Flight No
Southwest Airlines	WN801

05:55

Airline	Flight No
Southwest Airlines	WN3788

VIEW FLIGHTS

Saturday

00:50

Airline	Flight No
Southwest Airlines	WN801

12:05

Airline	Flight No
Southwest Airlines	WN339

12:15

Airline	Flight No
Southwest Airlines	WN940

VIEW FLIGHTS

Sunday

06:40

Airline	Flight No
Southwest Airlines	WN940

11:00

Airline	Flight No
Southwest Airlines	WN3577

VIEW FLIGHTS

Instead of flying from Oakland International Airport you could consider a few airports that are close by. Please see that table below of alternative routes.

Alternative Direct Routes

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

Over the past 10 years flight regulations have become very strict so we advise you to leave plenty of time to check in and get through customs.

Looking for the best car hire deals?

Search for a cheap rental car in Chicago Midway

Flight Price FAQ - Oakland (OAK) to Chicago (MDW)

1+ STOP(S)

What is the cheapest flight one way from Oakland OAK to Chicago MDW?

The cheapest flight one way from Oakland OAK to Chicago MDW is £44.81 ($59 €53.12)

£44.81

$59 | €53.12

Check Latest Price

1+ STOP(S)

What is the cheapest return flight from Oakland OAK to Chicago MDW?

The cheapest return flight from Oakland OAK to Chicago MDW is £89.61 ($118 €106.24)

£89.61

$118 | €106.24

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Important Note: Prices shown are taken from searches performed for flights operating during the current month. Please use the "Latest Price" buttons to get the most up to date airfares.