Cheap Flights from Oakland (OAK) to Chicago (ORD) from AU$263

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

Prices were available within the past 7 days and start at AU$263 for one-way flights and AU$696 for round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Mon., 20 May - Sun., 26 May
OAK
Oakland
ORD
Chicago
AU$696 Return, found 5 days ago
AU$696
Return
found 5 days ago
Select Alaska Airlines flight, departing Mon., 20 May from Oakland to Chicago, returning Sun., 26 May, priced at AU$696 found 5 days ago
Delta
Wed., 28 Aug. - Mon., 2 Sep.
OAK
Oakland
ORD
Chicago
AU$704 Return, found 3 days ago
AU$704
Return
found 3 days ago
Select Delta flight, departing Wed., 28 Aug. from Oakland to Chicago, returning Mon., 2 Sep., priced at AU$704 found 3 days ago
Alaska Airlines
Mon., 20 May - Sun., 26 May
OAK
Oakland
ORD
Chicago
AU$731 Return, found 5 days ago
AU$731
Return
found 5 days ago
Select Alaska Airlines flight, departing Mon., 20 May from Oakland to Chicago, returning Sun., 26 May, priced at AU$731 found 5 days ago
Alaska Airlines
Mon., 20 May - Sun., 26 May
OAK
Oakland
ORD
Chicago
AU$742 Return, found 5 days ago
AU$742
Return
found 5 days ago
Select Alaska Airlines flight, departing Mon., 20 May from Oakland to Chicago, returning Sun., 26 May, priced at AU$742 found 5 days ago
Delta
Wed., 28 Aug. - Mon., 2 Sep.
OAK
Oakland
ORD
Chicago
AU$743 Return, found 3 days ago
AU$743
Return
found 3 days ago
Select Delta flight, departing Wed., 28 Aug. from Oakland to Chicago, returning Mon., 2 Sep., priced at AU$743 found 3 days ago
Delta
Wed., 28 Aug. - Mon., 2 Sep.
OAK
Oakland
ORD
Chicago
AU$747 Return, found 3 days ago
AU$747
Return
found 3 days ago
Select Delta flight, departing Wed., 28 Aug. from Oakland to Chicago, returning Mon., 2 Sep., priced at AU$747 found 3 days ago
Alaska Airlines
Mon., 20 May - Sun., 26 May
OAK
Oakland
ORD
Chicago
AU$763 Return, found 5 days ago
AU$763
Return
found 5 days ago
Select Alaska Airlines flight, departing Mon., 20 May from Oakland to Chicago, returning Sun., 26 May, priced at AU$763 found 5 days ago
Alaska Airlines
Mon., 20 May - Sun., 26 May
OAK
Oakland
ORD
Chicago
AU$767 Return, found 5 days ago
AU$767
Return
found 5 days ago
Select Alaska Airlines flight, departing Mon., 20 May from Oakland to Chicago, returning Sun., 26 May, priced at AU$767 found 5 days ago
Alaska Airlines
Mon., 20 May - Sun., 26 May
OAK
Oakland
ORD
Chicago
AU$779 Return, found 5 days ago
AU$779
Return
found 5 days ago
Select Alaska Airlines flight, departing Mon., 20 May from Oakland to Chicago, returning Sun., 26 May, priced at AU$779 found 5 days ago
Delta
Wed., 28 Aug. - Mon., 2 Sep.
OAK
Oakland
ORD
Chicago
AU$780 Return, found 3 days ago
AU$780
Return
found 3 days ago
Select Delta flight, departing Wed., 28 Aug. from Oakland to Chicago, returning Mon., 2 Sep., priced at AU$780 found 3 days ago
Flight from Oakland to Chicago route information
Origin airport
Oakland Intl.
Destination airport
O'Hare Intl.
Return price
AU$696
Distance
2929 km
Average flight time
7 hours 5 mins

Your quick guide to flights from Oakland to Chicago

Pick up great flights from Oakland to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Oakland to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Oakland to Chicago that take around hours.

Find cheap flights from Oakland to Chicago

From the great flight deals with prices currently ranging from AU$696 to AU$780, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Oakland to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in May.

Reasons to book your flight from Oakland to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Oakland to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Frequently asked questions

How much is a flight from OAK to O'Hare Intl. Airport (ORD)?
If you’re planning on travelling between Oakland Intl. Airport and ORD, round-trip journeys start from AU$696. This price is based on fares 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 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 OAK to ORD?
Each air carrier has its own set of terms and conditions. If you decide to cancel your getaway, visit our Customer Service Portal.
How do I find cheap flights from OAK to O'Hare Intl. Airport (ORD) 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 (OAK) to O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Oakland Intl. Airport to O'Hare Airport?
Around 3 000 kilometres separates Oakland and Chicago, so pack something to help you fill in a few hours. That latest bestseller you’re eager to read will be just the ticket.
Which airlines fly direct from Oakland Intl. Airport to ORD?
If you want to fly straight from OAK to O’Hare Airport, you’ll have to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly between these airports.
Are Oakland Intl. Airport (OAK) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from Oakland Intl. Airport (OAK) to O’Hare Airport can be hit-or-miss. It is possible to find a bargain, but then again, you could miss out entirely! If you’d prefer to play it safe and start your trip planning early on, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines publish their prices so far in advance. Our top tip? Check back often as updates are made frequently.
Oakland Airports

San Francisco

San Francisco Intl. to Chicago
AU$277.10

San Jose

Norman Y. Mineta San Jose Intl. to Chicago
AU$483.71
*Available to Expedia members.