CA $176 Cheap Flights from Oakland (OAK) to Chicago (ORD)

You can find one-way and return flights from OAK to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when OAK to ORD ticket fares go up or down.

If you're looking for the cheapest time to fly from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.), February is typically your best bet. You can expect average return fares around CA$342 during this month. Other budget-friendly months for this route include August and September.

Enter OAK to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Southwest Airlines is one of the cheapest airlines offering connecting return flights from Oakland Intl. (OAK) to O'Hare Intl. (ORD), with prices starting from around CA$365 for flights that can be booked for departure within the next year. These flights typically include a layover in San Diego Intl. (SAN). These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

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.

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 flights around CA$342. These months can offer a good balance of affordability and availability, allowing you to find flights that suit your schedule and budget.

While there aren't any direct flights, you'll find approximately 14 connecting flights per day from Oakland Intl. (OAK) to O'Hare Intl. (ORD). Some common connection points include Salt Lake City Intl. (SLC), Seattle - Tacoma Intl. (SEA), and Portland Intl. (PDX).

The earliest flight from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 5:00 AM. This service is offered by Southwest Airlines. This is a seasonal service, active in June and July. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

You'll typically find the most flights from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Monday, with around 21 flights available. This gives you a good selection of options to choose from. Major airlines on this route include Southwest Airlines, Alaska Airlines, and Delta. While Monday is the busiest, flight options are fairly consistent throughout the week, so you'll have plenty of choices no matter when you plan to travel.

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, from 6am to 9am. Many major carriers, including Southwest Airlines, Alaska Airlines and Delta, offer flights during this window. Many travellers prefer these times because it allows for an early start to their journey, getting them to their destination with plenty of day left.

There are no nonstop flights from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (ORD-O'Hare Intl.). If you're looking for a flight with one stop, you can expect the journey to take around 9 hours. Flights with two or more stops will typically take longer, averaging about 12 hours 30 minutes. The distance between these two airports is approximately 2947 kilometres. Keep in mind that actual flight times can vary due to factors like layover duration, routing, and weather conditions.

You can fly business class or first class between OAK and ORD. You can fly business class with Delta.

First class cabins are available on Alaska Airlines and Delta.

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.

If you're planning to travel to Chicago from Oakland Intl. (OAK), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Salt Lake City Intl. (SLC), San Diego Intl. (SAN), or Portland Intl. (PDX) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

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.

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.

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.