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

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

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Flight from Oakland to Chicago route information
Origin airport
Oakland Intl.
Destination airport
Midway Intl.
Distance
2944 km
Average flight time
8 hours 14 mins

Oakland to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Oakland to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with OAK to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Oakland for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from Oakland Intl. Airport (OAK) to Midway Airport?
If you're travelling between Oakland Intl. Airport (OAK) and Midway Intl. Airport (MDW), round-trip journeys start from . This price is based on airfares listed within the last 7 days on Expedia for flights departing within the next year, so don't wait around. Book today and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the simple instructions on our Customer Service Portal.
How do I find cheap flights from Oakland Intl. Airport to Midway Intl. Airport (MDW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Oakland Intl. Airport to Midway Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from OAK to Chicago Airport?
Around 3,000 kilometres separates Oakland and Chicago, so pack some entertainment to help you fill in a couple of hours. That juicy novel you haven't had time to start will be just the ticket.
Which airlines fly direct from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
If you want to fly straight from OAK to MDW, Southwest Airlines (WN) is a popular choice. It operates 60 flights each month between Oakland and Chicago.
Are Oakland Intl. Airport (OAK) to MDW flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes find a bargain, with some super cheap fares from Oakland Intl. Airport (OAK) to Chicago Airport popping up a few weeks prior to the departure date. If you'd rather plan ahead, Expedia compares and updates all the best flight deals continually — as early as 12 months in advance in some cases. It depends on the carrier though, as not all airlines quote prices that far in advance.
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