Title: CA $198 Cheap Flights from Oakland (OAK) to Chicago (ORD) - Expedia.ca ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $198 Cheap Flights from Oakland (OAK) to Chicago (ORD) [View CA $198 flight on Mon, Nov 17, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:OAK,to:ORD,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:197.30&airProductToken=AQpfCi4IwaYBEgQyMDg2GI5QIJIBKNOv_QIw17D9AjhYQABYAWoCU1ZyCEdIMk9BVkJOCi0IwaYBEgMzMjgYkgEgrhwo1LH9AjDGs_0COFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Oakland Intl. Airport (OAK) to Chicago O'Hare International Airport (ORD) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:oak,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:oak,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:oak,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:oak,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:oak,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:oak,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Hawaiian Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_HA.svg) Hawaiian Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:oak,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:oak,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Oakland (OAK) to Chicago (ORD) Prices were available within the past 7 days and start at CA $198 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ## Find the cheapest month to fly from Oakland (OAK) to Chicago (ORD) ### January is typically the cheapest month to fly From CA $147 - CA $458 per traveller. ## Frequently asked questions ### How much is a flight from OAK to O'Hare Airport? > If you're travelling between Oakland Intl. Airport and O'Hare Airport, 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 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 Oakland Intl. Airport (OAK) to O'Hare Airport? > Each air carrier has its own terms and conditions. If you do decide to cancel, follow the instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from OAK to O'Hare Airport that have flexible change policies? > Flights from OAK to O'Hare Intl. Airport (ORD) with flexible change policies are available from several airlines. Simply use our "No change fees" filter during your search. You'll only need to cover the cost difference between flights, without any additional fees to worry about. ### How many hours is the flight from Oakland Intl. Airport to O'Hare Airport? > You may like to bring your own entertainment (like some downloaded podcasts), as it takes an average of 6 hours and 26 minutes to reach O'Hare Intl. Airport (ORD) from OAK. A good pair of noise-cancelling headphones will be handy too. ### How far is the flight from Oakland Intl. Airport to O'Hare Intl. Airport (ORD)? > The flying distance from Oakland Intl. Airport (OAK) to O'Hare Airport is 3,000 kilometres. Sneak in a nap or read a good book and the trip will zip on by. ### Which airlines fly direct from Oakland Intl. Airport to ORD? > If you want to travel straight from OAK to ORD, you'll need to book a flight with one or more stops. Unfortunately, there are no airlines that fly directly between these airports. ### Are OAK to ORD flight tickets cheaper when they're purchased at the last minute? > Tickets from Oakland Intl. Airport (OAK) to O'Hare Airport are available up to 12 months prior to departure on Expedia. And although you may occasionally pick up a fantastic last-minute deal, it's not something you should count on. Also, booking your flights well in advance means you'll have more options — and you can avoid getting stuck in the dreaded middle seat! We frequently update our fares to bring you the biggest bargains, so check back often for all the latest specials. ## Travel information | Origin airport | Oakland Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Distance | 2929 km | | Average flight time | 7 hours 50 mins | ## Book with confidence ### Oakland to Chicago Flights **The easy way to book your flights from Oakland to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Oakland 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 O'Hare 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 Oakland to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Oakland Intl., OAK to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Oakland to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Oakland currently is just rising to .   Here are more money-saving tips:  - Fly in when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - 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 Chicago from Oakland**  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. 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