£125 Cheap Flights from Oakland (OAK) to Chicago (ORD)

View £125 flight on Mon, 13 Jul 2026Opens in a new window

Popular airlines from Oakland Intl. Airport (OAK) to Chicago O'Hare International Airport (ORD)

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

Prices were available within the past 7 days and start at £125 for one-way flights and £365 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Thu, 8 Oct - Mon, 12 Oct
OAK
Oakland
ORD
Chicago
£365 Return, found 6 days ago
£365
Return
found 6 days ago
Select Alaska Airlines flight, departing Thu, 8 Oct from Oakland to Chicago, returning Mon, 12 Oct, priced at £365 found 6 days ago
Alaska Airlines
Wed, 29 Jul - Mon, 3 Aug
OAK
Oakland
ORD
Chicago
£380 Return, found 4 days ago
£380
Return
found 4 days ago
Select Alaska Airlines flight, departing Wed, 29 Jul from Oakland to Chicago, returning Mon, 3 Aug, priced at £380 found 4 days ago
Alaska Airlines
Thu, 8 Oct - Mon, 12 Oct
OAK
Oakland
ORD
Chicago
£407 Return, found 6 days ago
£407
Return
found 6 days ago
Select Alaska Airlines flight, departing Thu, 8 Oct from Oakland to Chicago, returning Mon, 12 Oct, priced at £407 found 6 days ago
Alaska Airlines
Thu, 8 Oct - Mon, 12 Oct
OAK
Oakland
ORD
Chicago
£410 Return, found 6 days ago
£410
Return
found 6 days ago
Select Alaska Airlines flight, departing Thu, 8 Oct from Oakland to Chicago, returning Mon, 12 Oct, priced at £410 found 6 days ago

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 £365. 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.

Frequently asked questions

What is the cheapest month to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
February is typically the cheapest month to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.), with average return fares of approximately £342. This is about 41% lower than the average price throughout the year. February often sees lower prices as it's outside of peak holiday travel and before the spring break rush, leading to less demand. Other cheap months to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) include August and September.
How do I find cheap flights from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Based on booking data from the past year, the cheapest months to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) are typically February and August, with average return flight prices around £342. These months can be a great option if you're looking for the best value on your trip.
How many flights per day from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 23 connecting flights per day from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.). Some common connection points include Salt Lake City Intl. (SLC), Seattle - Tacoma Intl. (SEA), and San Diego Intl. (SAN).
What is the earliest flight from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at approximately 5:00 AM local time, operated by WN. This is a seasonal service active in June and July. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Oakland Intl. (OAK) to O'Hare Intl. (ORD) on a Monday, with around 22 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Southwest Airlines, Alaska Airlines, and Delta Air Lines. Flight schedules are consistent throughout the week.
What are the most popular departure times for flights from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, between 6am and 9am. This accounts for around 33% of total traffic. Southwest Airlines and Alaska Airlines offer flights during this window. Many travelers prefer these times because it allows for an early start to their journey, getting them to their destination with plenty of day left.
How long does it take to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A flight from OAK to ORD with a layover takes around 7 hours, with the route covering approximately 1,831 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for OAK to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Oakland Intl. (OAK)?
When traveling from Oakland Intl. (OAK) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Salt Lake City Intl. (SLC), San Diego Intl. (SAN), Portland Intl. (PDX) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Oakland Intl.
Destination airport
O'Hare Intl.
Return price
£365
Distance
2929 km

Book with confidence

Compare flights from Oakland to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Oakland to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Oakland Intl. to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Oakland Intl. (OAK) to O'Hare Intl. (ORD)

The easiest way to view the best deals on flights from Oakland to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Oakland Intl. to O'Hare Intl. start at just £365 and range up to £410.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Oakland and Chicago
  • booking your flight during October, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Oakland to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Oakland Intl. to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from Oakland to Chicago easily and book with confidence

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*Available to Expedia members.