MDW to OAK (Chicago to Oakland) Flights

Last Minute Flights from MDW to OAK

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

OriginDestinationTravel DatesFlights From*
MDWOaklandJune 21 to July 11$352
*Prices include taxes and fees

Cheapest MDW to OAK Flights

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

OriginDestinationTravel DatesFlights From*
MDWOaklandOctober 25 to October 28$194
MDWOaklandOctober 25 to October 28$194
MDWOaklandOctober 25 to October 28$197
MDWOaklandAugust 26 to September 13$267
*Prices include taxes and fees
MDW to OAK Flight Details
Origin airport
Midway Intl.
Origin airport IATA code
MDW
Destination airport
Oakland Intl.
Destination airport IATA code
OAK
Distance
1840 mi

Frequently asked questions

What airlines fly direct from Chicago Airport to Oakland Intl. Airport?
Unfortunately, you can’t fly straight from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK). Make your way to Oakland by booking a flight with one or more stops in between. If you’re not in a hurry, why not spend a couple of days in your layover city?
How many flights are there from MDW to OAK?
There are about 11 flights from Chicago, IL (MDW-Midway Intl.) to Oakland, CA (OAK-Oakland Intl.) a week. Book one of them and you’ll be wandering around the sights of Oakland before you know it!
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Oakland, CA (OAK-Oakland Intl.)?
It takes approximately 8 hours and 4 minutes to jet from Chicago, IL (MDW-Midway Intl.) to Oakland, CA (OAK-Oakland Intl.). That’s ample time to start your travel diary, do some eleventh-hour trip planning or read about the fun experiences you can have in Oakland.
What is the flight distance from Chicago, IL (MDW-Midway Intl.) to Oakland, CA (OAK-Oakland Intl.)?
At 1,850 miles (3,000 1), this medium-haul flight is no endurance event, but it’s no walk in the park either. Touch down in Oakland feeling rested and recharged by having a nap along the way.
How many afternoon flights are there from MDW to OAK?
With around 11 afternoon and evening flights every week from MDW to OAK, there’s no need to stress about waking while it’s still dark outside. Volaris (Y4) offers 11 weekly services after midday, with its earliest departure scheduled for 8:45PM.
What is the earliest departure time out of Chicago to Oakland?
If you’re not an early bird, you’ll be pleased to know that the earliest plane from MDW takes off at 8:45PM. Book this flight and you’ll be landing at OAK at 5:59PM.
What is the latest departure time out of Chicago to Oakland?
Reserve a seat on the 10:41PM flight from MDW, landing at OAK at 4:59PM, and give yourself time to complete any last-minute vacation preparations. This is the latest flight you can catch on this route.
What is the average price from Chicago to Oakland?
Round-trip journeys for this route start from about $194. When you’re ready to lock in your trip, we’ll help you land the best possible price. 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.

Chicago to Oakland Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Chicago to Oakland 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 MDW to OAK, 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 Chicago to Oakland, 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.