$69 Cheap Flights from Oakland (OAK) to Chicago (ORD)

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Cheap Flights from Oakland to Chicago (OAK-ORD)

Prices were available within the past 7 days and start at $69 for one-way flights and $138 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Flights from Oakland (OAK) to Chicago (ORD)
Origin airport
Oakland Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Spirit Airlines, Sun Country Airlines
Roundtrip price
$137
Distance
1831 mi

Oakland to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Oakland to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Oakland to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is $69 now!

Frequently asked questions

How much is a one-way flight from Oakland Intl. Airport (OAK) to ORD?
Get ready to score a terrific deal, because Oakland flights to Chicago start from $69. This info is based on the lowest fare found on Expedia for this route departing in the next three months. This airfare is for an Spirit Airlines flight, departing from Oakland Intl. Airport on August 28 2024 and touching down at ORD. This price was last updated on June 4 2024 and has not changed since.
Is it cheaper to buy a plane ticket from OAK to ORD last minute?
When it’s time to book your flights, being organized pays off. While it’s possible to find a deal on an Oakland Intl. Airport to O’Hare Intl. Airport (ORD) flight at the last minute, tickets usually don’t get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days ahead. For international trips it’s between three and four months.
What airports do you fly into for Chicago from Oakland?
O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are your options when setting off from Oakland to Chicago. About 16 mi northwest of central Chicago, O’Hare Intl. Airport (ORD) is the city’s main entry point. Take into account things such as flight schedules and the distance to your hotel before deciding on an airport. Wrigley Field and Millennium Park are two terrific attractions to check out when you reach your destination.
Can I change the date of my flight from Oakland Intl. Airport to ORD?
We know life happens and plans change, so Expedia is here to help make amending your trip as easy as possible. To start, find your Oakland Intl. Airport (OAK) to O’Hare Intl. Airport (ORD) itinerary through the Expedia Trips portal and browse the ticket rules and conditions to see if change fees apply. If you booked in the last 24 hours, some airlines will allow you to cancel for free and book new flights. If you bought your ticket more than 24 hours ago, connect with us via our Customer Service portal to see how we can help.
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