Cheap Flights from Oakland (OAK) to Chicago (MDW)

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Popular airlines from Oakland Intl. Airport (OAK) to Chicago Midway Airport (MDW)

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Frequently asked questions

Is it cheaper to buy a plane ticket from Oakland Intl. Airport (OAK) to Chicago Airport last minute?
Booking your trip from Oakland Intl. Airport to Midway Intl. Airport (MDW) last minute could save you a pretty penny if you're lucky to find an epic deal. However, airfares usually don't get cheaper closer to the departure date. If you wait, flights could also be booked out or the best seats gone (because no one wants the middle seat). If you'd rather not take any chances, book well in advance of your departure date. Don't forget that some of the biggest bargains can be found up to a year in advance. If your favorite carrier hasn't released its airfares yet, check back regularly as deals are updated on Expedia constantly.
What airports do you fly into for Chicago from Oakland?
With Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to pick from, traveling from Oakland to Chicago is a cinch. The city's key hub, Midway Intl. Airport (MDW), is about 14 kilometers southwest of the downtown area. Apart from the price of fares, consider factors like transportation options from the airport and the distance to your hotel when choosing where to fly into. Get your Chicago vacation off to an exciting start by discovering Wrigley Field and Millennium Park.
Can I change the date of my flight from Oakland Intl. Airport to MDW?
It's a breeze to make changes to your OAK to Chicago Airport trip yourself. Access your itinerary via the Expedia Trips portal and tap "change flight." Look around for new flights and secure the one that fits your new plans. You'll see an estimate of your flight change cost, if applicable. You can also head to our Customer Service portal to connect with our Virtual Agent and get answers to your questions.

Travel information

Origin airport
Oakland Intl.
Destination airport
Midway Intl.
Distance
2944 km
Average flight time
6 hours 5 mins

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Oakland to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Oakland to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Oakland to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Oakland to Chicago Flights