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Cheap Flights from Chicago to Oakland from $208

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Cheap ORD to OAK Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 21 - Sat, Aug 24
ORD
Chicago
to
OAK
Oakland
$208

roundtrip

just found

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Sat, Aug 24 - Wed, Aug 28
ORD
Chicago
to
OAK
Oakland
$208

roundtrip

found 2 hours ago

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Sat, Aug 24 - Tue, Aug 27
ORD
Chicago
to
OAK
Oakland
$212

roundtrip

just found

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Sat, Aug 24 - Wed, Aug 28
ORD
Chicago
to
OAK
Oakland
$212

roundtrip

found 2 hours ago

Open ORD to OAK flights search result page
Sat, Aug 24 - Tue, Aug 27
ORD
Chicago
to
OAK
Oakland
$213

roundtrip

just found

Open ORD to OAK flights search result page
Sat, Aug 24 - Wed, Aug 28
ORD
Chicago
to
OAK
Oakland
$213

roundtrip

found 2 hours ago

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Sat, Sep 7 - Wed, Sep 11
ORD
Chicago
to
OAK
Oakland
$216

roundtrip

found 1 hour ago

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Tue, Sep 17 - Wed, Sep 25
ORD
Chicago
to
OAK
Oakland
$216

roundtrip

found 1 hour ago

Open ORD to OAK flights search result page
Sat, Aug 24 - Tue, Aug 27
ORD
Chicago
to
OAK
Oakland
$217

roundtrip

just found

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Sat, Aug 24 - Wed, Aug 28
ORD
Chicago
to
OAK
Oakland
$217

roundtrip

found 2 hours ago

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Sat, Sep 7 - Wed, Sep 11
ORD
Chicago
to
OAK
Oakland
$220

roundtrip

found 1 hour ago

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Sat, Aug 24 - Fri, Sep 6
ORD
Chicago
to
OAK
Oakland
$221

roundtrip

found 8 hours ago

Open ORD to OAK flights search result page
Sat, Sep 7 - Wed, Sep 11
ORD
Chicago
to
OAK
Oakland
$221

roundtrip

found 1 hour ago

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Wed, Oct 9 - Sat, Oct 12
ORD
Chicago
to
OAK
Oakland
$222

roundtrip

found 7 hours ago

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Sat, Aug 24 - Tue, Aug 27
ORD
Chicago
to
OAK
Oakland
$222

roundtrip

just found

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Sat, Aug 24 - Tue, Aug 27
ORD
Chicago
to
OAK
Oakland
$224

roundtrip

just found

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Tue, Oct 29 - Tue, Oct 29
ORD
Chicago
to
OAK
Oakland
$272

roundtrip

found 1 day ago

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Tue, Nov 12 - Tue, Nov 19
ORD
Chicago
to
OAK
Oakland
$300

roundtrip

found 9 hours ago

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Thu, Nov 7 - Tue, Nov 12
ORD
Chicago
to
OAK
Oakland
$318

roundtrip

found 2 days ago

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Fri, Oct 25 - Mon, Oct 28
ORD
Chicago
to
OAK
Oakland
$441

roundtrip

found 13 hours ago

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Chicago to Oakland route information

Origin Airport O'Hare Intl.
Destination Airport Oakland Intl.
Airlines Serving Alaska Airlines, American Airlines, Delta, JetBlue Airways, Spirit Airlines
Flight Price $208
Distance 1,831 mi

Chicago

MDW-Midway Intl.

$332.40

Top Routes from Chicago

Top Routes to Oakland

Cheap ORD to OAK Flights

  • Question : What is the cheapest airline flying from Chicago to Oakland?
    Answer : Spirit Airlines is your best flying friend for finding that sought-after low fare. They're offering fares as low as $163, while prices for other flights are as high as $937.
  • Question : Which airline has the least delays from Chicago to Oakland?
    Answer : Booking with FedEx means you will arrive to Oakland pretty close to the time your ticket states. In fact, this timely airline has an 87% average for landing before the plane turns into a pumpkin. It never hurts to be prepared. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.
  • Question : Can I change the date of my flight?
    Answer : You sure can adjust your departure date and you may save money by changing when you leave. The cheapest day to fly in July is Thursday. Flexibility is key when booking travel to help keep costs down.
  • Question : How much is a plane ticket to Oakland (OAK) from Chicago (ORD)?
    Answer : Cost can range from $163 to $937, prices for ORD to OAK change less than most routes in the United States. Prices are usually lower the further out you book.
  • Question : Is there an alternative airport near Oakland?
    Answer : Yes, you can fly into another airport. The other airport is San Francisco International Airport (SFO) which is only 12 miles away and on average, flights are 11% cheaper for the upcoming two months. Save and put it towards your next trip.
  • Question : What is the cheapest day to fly to Oakland?
    Answer : Tickets are currently $198, which is 46% below the average price for this route. As of Jul 15th, the cheapest day to fly from Chicago to Oakland is Aug 13th.
  • Question : How many flights are there per day from Chicago to Oakland?
    Answer : Each day is different, but on average, you can expect to see only one available departure time. Compared to the average route departing the United States with nine flight times, you won't have as many options as most.

Chicago to Oakland Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Oakland will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Oakland.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with ORD to OAK flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to OAK with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Jul 7, 2019

Good flight, on time

A verified traveler
Chicago to Oakland · Spirit Airlines
Oct 16, 2018

Headrest not comfortable

A verified traveler
Chicago to Oakland · Spirit Airlines
Jul 30, 2018

Isles are wider check bag & carry on fees high, low weight limits, compare seats to AA flights. I will fly spirit again

A verified traveler
Chicago to Oakland · Spirit Airlines
Oct 31, 2016

I did not like being inexplicably charged for one carry-on bag at the end of the process, so I am going to try to avoid Spirit Airlines in the future.

A verified traveler
Chicago to Oakland · Spirit Airlines