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

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Getting to Oakland International Airport from Midway is very straight forward. There are 2 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
AirlinerMoTuWeThFrSaSuFirst FlightLast FlightFlights
Southwest Airlines111112105:2511:00VIEW FLIGHTS
flyExclusive0000010VIEW FLIGHTS

The most direct flights are offered by Southwest Airlines but they only offer 1 flight per week. This flight departs 05:25 and goes by the flight number WN2363

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
DayFlight TimesFlights
Monday
11:00
AirlineFlight  No
Southwest AirlinesWN2363
VIEW FLIGHTS
Tuesday
11:00
AirlineFlight  No
Southwest AirlinesWN2363
VIEW FLIGHTS
Wednesday
11:00
AirlineFlight  No
Southwest AirlinesWN2363
VIEW FLIGHTS
Thursday
11:00
AirlineFlight  No
Southwest AirlinesWN2363
VIEW FLIGHTS
Friday
05:25
AirlineFlight  No
Southwest AirlinesWN2363
VIEW FLIGHTS
Saturday
05:10
AirlineFlight  No
Southwest AirlinesWN199
12:00
AirlineFlight  No
flyExclusiveJRE837
13:30
AirlineFlight  No
Southwest AirlinesWN174
VIEW FLIGHTS
Sunday
05:25
AirlineFlight  No
Southwest AirlinesWN2363
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
RouteStopsDistanceFlying Time
Sacramento Mather to Chicago Midway04 Hours 10 Minutes
San Francisco to Chicago Midway04 Hours 19 Minutes
Mineta San Jose to Chicago Midway04 Hours 17 Minutes
Sacramento to Chicago Midway04 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)

DIRECT Southwest Airlines
What is the cheapest direct flight one way from Oakland OAK to Chicago MDW?
The cheapest direct flight one way from Oakland OAK to Chicago MDW is £122.97 ($161 €139.43)
£122.97
$161 | €139.43
Check Latest Price
DIRECT Southwest Airlines
What is the cheapest direct return flight from Oakland OAK to Chicago MDW?
The cheapest direct return flight from Oakland OAK to Chicago MDW is £238.30 ($312 €270.20)
£238.30
$312 | €270.20
Check Latest Price
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 £100.82 ($132 €114.32)
£100.82
$132 | €114.32
Check Latest Price
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.

Compare Flight Prices from OAK to MDW

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

Who flies from Oakland to Chicago?
The following airlines fly from Oakland (OAK) to Chicago (MDW): flyExclusive, Southwest Airlines.
How far is the flight from Oakland to Chicago?
The flight from Oakland to Chicago is 2,961KM or 1,840 miles.
How long does the flight from Oakland to Chicago to take?
The flight from Oakland to Chicago takes 4 Hours 18 Minutes.

Alternative Airports in United States with Connections from Oakland International Airport

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