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

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

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Find the cheapest month to fly from Chicago (MDW) to Oakland (OAK)

August is typically the cheapest month to fly

From ₹16,690 - ₹59,209 per traveller.

Frequently asked questions

How much is a flight from Chicago Airport to Oakland Intl. Airport (OAK)?
If you're planning on travelling from MDW to OAK, round-trip journeys start from . This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don't delay. 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 Midway Intl. Airport (MDW) to OAK?
This can vary from airline to airline, as each has its own set of terms and conditions. Visit the Customer Service Portal, where you'll find easy-to-follow instructions on how to cancel online.
How do I find cheap flights from MDW to Oakland Intl. Airport 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 MDW to Oakland Intl. Airport (OAK) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Chicago Airport to OAK?
Around 3,000 kilometres separates Chicago and Oakland, so pack some in-flight entertainment to help you while away a few hours. That novel you've yet to start will do the trick.
Which airlines fly direct from Chicago Airport to OAK?
A favourite with many frequent flyers, Southwest Airlines (WN) operates 52 monthly flights from Midway Intl. Airport (MDW) to OAK. Pick the one that fits with your travel schedule and book your ticket today.
Are Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK) flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Chicago Airport to Oakland Intl. Airport can be hit-or-miss. It is possible to find a bargain, but you could also completely miss out! If you'd rather start your travel planning early on, Expedia compares flight deals up to a year in advance. Just bear in mind that not all airlines list their prices so far in advance. Our advice? Check back often as prices are updated frequently.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Oakland Intl.
Distance
2944 km
Average flight time
4 hours 13 mins

Book with confidence

Book with confidence

Chicago to Oakland 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 Chicago to Oakland 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 Oakland.

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 MDW to OAK flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago 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 OAK 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.

Chicago to Oakland Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Oakland Airports

San Francisco

Chicago to San Francisco Intl.
₹32,438.00

San Jose

Chicago to Norman Y. Mineta San Jose Intl.
₹34,069.00
Chicago Airports

Chicago

O'Hare Intl. to Oakland
₹71,816.00
*Available to Expedia members.