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CA $225 Cheap Flights from Chicago (ORD) to Oakland (OAK)

View CA $225 flight on Fri, Oct 9, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at CA $225 for one-way flights and CA $460 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
ORD
Chicago
OAK
Oakland
CA $460 Roundtrip, found 6 days ago
CA $460
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 8 from Chicago to Oakland, returning Tue, Sep 15, priced at CA $460 found 6 days ago
Alaska Airlines
Fri, Jul 31 - Mon, Aug 3
ORD
Chicago
OAK
Oakland
CA $463 Roundtrip, found 5 days ago
CA $463
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Fri, Jul 31 from Chicago to Oakland, returning Mon, Aug 3, priced at CA $463 found 5 days ago
Delta
Fri, Jul 31 - Mon, Aug 3
ORD
Chicago
OAK
Oakland
CA $477 Roundtrip, found 5 days ago
CA $477
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jul 31 from Chicago to Oakland, returning Mon, Aug 3, priced at CA $477 found 5 days ago
Delta
Fri, Oct 9 - Sun, Oct 18
ORD
Chicago
OAK
Oakland
CA $488 Roundtrip, found 6 days ago
CA $488
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Oct 9 from Chicago to Oakland, returning Sun, Oct 18, priced at CA $488 found 6 days ago
Alaska Airlines
Fri, Sep 4 - Sun, Sep 6
ORD
Chicago
OAK
Oakland
CA $503 Roundtrip, found 5 days ago
CA $503
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Fri, Sep 4 from Chicago to Oakland, returning Sun, Sep 6, priced at CA $503 found 5 days ago
Alaska Airlines
Fri, Jul 31 - Mon, Aug 3
ORD
Chicago
OAK
Oakland
CA $504 Roundtrip, found 5 days ago
CA $504
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Fri, Jul 31 from Chicago to Oakland, returning Mon, Aug 3, priced at CA $504 found 5 days ago
Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
ORD
Chicago
OAK
Oakland
CA $507 Roundtrip, found 6 days ago
CA $507
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 8 from Chicago to Oakland, returning Tue, Sep 15, priced at CA $507 found 6 days ago
Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
ORD
Chicago
OAK
Oakland
CA $510 Roundtrip, found 6 days ago
CA $510
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 8 from Chicago to Oakland, returning Tue, Sep 15, priced at CA $510 found 6 days ago
Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
ORD
Chicago
OAK
Oakland
CA $512 Roundtrip, found 6 days ago
CA $512
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 8 from Chicago to Oakland, returning Tue, Sep 15, priced at CA $512 found 6 days ago
Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
ORD
Chicago
OAK
Oakland
CA $518 Roundtrip, found 6 days ago
CA $518
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 8 from Chicago to Oakland, returning Tue, Sep 15, priced at CA $518 found 6 days ago

Alternative airports near Oakland

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to San Francisco Intl. SFO. Cheapest option available. Average driving time to city centre is 32 minutes. Flights from CA $729
SFO
San Francisco Intl.
Cheapest
Average driving time to city centre32 min
Flights from CA $729

Frequently asked questions

How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland 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 Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
There are approximately 81 connecting flights per day from Chicago O'Hare International (ORD) to Oakland International (OAK). Some common connection points include Seattle - Tacoma International (SEA), Denver International (DEN), and Portland International (PDX).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.) typically departs at approximately 5:00 AM local time. This service is operated by United Airlines and Alaska Airlines. 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 Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
You'll typically find the most flights from Chicago O'Hare International Airport (ORD) to Oakland International Airport (OAK) on a Friday, with around 28 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United Airlines, Alaska Airlines, and Southwest Airlines. Flight schedules are consistent throughout the week, with Friday offering only slightly more options than other days.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
The most popular departure times for flights from Chicago O'Hare International Airport (ORD) to Oakland International Airport (OAK) are in the early morning, from 6am to 9am. Approximately 43% of passengers prefer this time window. Many major carriers, including Southwest Airlines, Delta Air Lines and Alaska Airlines, offer flights during this window. These times work well because you can get an early start to your travel day and arrive in Oakland with plenty of time.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
A flight from ORD to OAK with a layover takes around 6 hours 50 minutes, 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 Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
Select the "Business class" and "First class" filters when looking for ORD to OAK 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 Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland 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 Oakland from O'Hare Intl. (ORD)?
If you're planning to travel to Oakland from O'Hare Intl. (ORD), you can fly into Oakland Intl. (OAK) Some flights may connect through major hubs like Harry Reid Intl. (LAS), Denver Intl. (DEN), Love Field (DAL) before reaching Oakland. 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 Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland 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 Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland 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 Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Oakland, CA (OAK-Oakland 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
O'Hare Intl.
Destination airport
Oakland Intl.
Airlines serving
Alaska Airlines, Delta
Roundtrip price
CA $459
Distance
2929 km

Book with confidence

Chicago to Oakland Flights

The easy way to book your flights from Chicago to Oakland 

With Expedia, it’s simple to find and book flights to Oakland from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Oakland Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Oakland today, tomorrow, or this week.  

 

Save dollars with cheap flights from O'Hare Intl., ORD to Oakland Intl., OAK 

Sort your search results by price to find great deals on your flight from Chicago to Oakland—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Oakland from Chicago currently is just CA $460 rising to CA $518.  

Here are more money-saving tips: 

  • Fly in September when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Oakland  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Oakland from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Oakland with Expedia today.

Chicago to Oakland Flights

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