MDW to OAK (Chicago to Oakland) Flights

Last Minute Flights from MDW to OAK

Best airfare and ticket deals for MDW to OAK flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
MDWOaklandApril 27 to April 30$290
*Prices include taxes and fees

Cheapest MDW to OAK Flights

Best airfare and ticket deals for MDW to OAK flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
MDWOaklandMay 4 to May 11$243
MDWOaklandMay 6 to May 11$257
MDWOaklandApril 20 to May 11$258
MDWOaklandAugust 6 to August 10$263
*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

Which airlines with flights from Midway International Airport to Oakland International Airport allow free cancellation due to COVID-19?
To find airlines that allow COVID-19 related changes, simply use our convenient filter function. Begin by entering your dates. Then, once all the available flights are displayed, check the “No change fee” box underneath the “Flexible change policies” subheading to the left. Read over the airline’s rules and regulations before locking in your MDW to Oakland International Airport ticket.
What airlines fly direct from MDW to Oakland, CA Airport (OAK-Oakland Intl.)?
Get your trip off to a quick start with Southwest Airlines (WN). This renowned carrier offers 60 nonstop flights every month from Chicago Airport to Oakland, CA Airport (OAK-Oakland Intl.), so you’ll be strolling around Oakland in no time!
How many flights are there from MDW to OAK?
About 58 flights are available per day between Chicago, IL Airport (MDW-Midway Intl.) and Oakland, CA Airport (OAK-Oakland Intl.). Fasten your seat belt because your plane to Oakland is ready to take to the skies.
How long does it take to fly from Chicago, IL Airport (MDW-Midway Intl.) to Oakland, CA Airport (OAK-Oakland Intl.)?
While you won’t be in your seat forever from Chicago, IL Airport (MDW-Midway Intl.) to Oakland, CA Airport (OAK-Oakland Intl.), 6 hours and 5 minutes isn’t necessarily a quick ride either. Inquire about upgrading your ticket if you’re after a few extra inches of space.
What is the flight distance from Chicago, IL Airport (MDW-Midway Intl.) to Oakland, CA Airport (OAK-Oakland Intl.)?
Covering a distance of 1850 miles (3000 km), you’ll be in the air for some time during this medium-haul journey. Like more legroom? Pick an aisle seat. Otherwise, sit at the window and stare out at the landscapes between Chicago and Oakland.
How many morning flights are there from MDW to OAK?
Every week, 198 morning services depart from MDW to OAK, with 198 offered by Southwest Airlines (WN). If you want to be en route to your destination as early as you can, WN’s first flight takes off at 5:50AM.
How many afternoon flights are there from MDW to OAK?
Book one of the 211 weekly afternoon and evening flights from MDW to OAK and sleep in a little later. Leading carrier Southwest Airlines (WN) offers 208 of these later flights which leave from 12:05PM.
What is the earliest departure time out of Chicago to Oakland?
Fly out of MDW at 5:50AM and touch down at OAK at 2:40PM. This is the earliest service you can catch on this route.
What is the latest departure time out of Chicago to Oakland?
Book a seat on the 9:55PM flight out of MDW, touching down at OAK at 6:40PM, and give yourself time to attend to any last-minute vacation preparations. This is the latest flight available on this route.
What is the average price from Chicago to Oakland?
On average, the most competitive price for a round-trip airfare from MDW to OAK is $243. Steal yourself a great bargain by locking in your seats soon. 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 perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from MDW to OAK, we’ve got you covered here at Flights.com.

We present you with some of the hottest 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.