OAK to MDW (Oakland to Chicago) Flights

Last Minute Flights from OAK to MDW

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
OAKChicagoMay 4 to May 10$500
*Prices include taxes and fees

Cheapest OAK to MDW Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
OAKChicagoJune 4 to June 7$207
OAKChicagoJune 1 to June 7$217
OAKChicagoJune 4 to June 7$227
OAKChicagoJuly 19 to July 22$267
*Prices include taxes and fees
OAK to MDW Flight Details
Origin airport
Oakland Intl.
Origin airport IATA code
OAK
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
1840 mi

Frequently asked questions

What airlines fly direct from Oakland Intl. Airport to Midway Airport?
Unfortunately, there aren’t any air carriers that fly straight from Oakland Intl. Airport to Chicago Airport. If you want to reach Chicago, book a journey with one or more stops.
How many flights are there from OAK to MDW?
Each week, 12 flights take to the skies from Oakland, CA (OAK-Oakland Intl.) for Chicago, IL (MDW-Midway Intl.). Pack your suitcase — the vibrant city of Chicago is waiting!
How long does it take to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (MDW-Midway Intl.)?
Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (MDW-Midway Intl.) takes on average 7 hours and 48 minutes. That’s the perfect amount of time to binge-watch an epic new series, get lost in a podcast or catch some z’s.
What is the flight distance from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (MDW-Midway Intl.)?
Approximately 1,850 miles (3,000 1). If you travel regularly and have stored up an useful number of air miles, this medium-haul journey may be the perfect time to use them for an upgrade.
How many afternoon flights are there from OAK to MDW?
With around 12 afternoon and evening flights every week from OAK to MDW, there’s no need to stress about waking with the roosters. Volaris (Y4) offers 12 weekly services after midday, with its earliest scheduled departure at 1:51PM.
What is the earliest departure time out of Oakland to Chicago?
The first flight of the day leaves OAK at 1:51PM and sets down at MDW at 10:23AM. There’ll be no need to wake up too early to make this trip.
What is the latest departure time out of Oakland to Chicago?
From OAK, the last flight departs at 6:39PM and comes in at 8:47AM at MDW. If you’re not into early mornings, this is the flight to book.
What is the average price from Oakland to Chicago?
Flights from OAK to MDW start at around $207. You’ll want to get a move on, because deals this good always go quickly! This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Oakland to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Oakland to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from OAK to MDW, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from Oakland to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.