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Flights from Oakland Intl. Airport (OAK) to Chicago, IL (CHI-All Airports)
Flights to Illinois
United States of America
Flights
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Popular airlines from Oakland Intl. Airport (OAK) to Chicago

Alaska Airlines
Southwest Airlines
Delta
Frontier Airlines

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Cheap Flights from Oakland to Chicago (OAK-CHI)

Prices were available within the past 7 days and start at CA $176 for one-way flights and CA $504 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Wed, Jul 29 - Tue, Aug 4

OAK

Oakland

ORD

Chicago

CA $504

Roundtrip

Found 3 days ago

Select Alaska Airlines flight, departing Wed, Jul 29 from Oakland to Chicago, returning Tue, Aug 4, priced at CA $504 Found 3 days ago

Thu, Aug 27 - Sun, Aug 30

OAK

Oakland

ORD

Chicago

CA $515

Roundtrip

Found 1 day ago

Select Alaska Airlines flight, departing Thu, Aug 27 from Oakland to Chicago, returning Sun, Aug 30, priced at CA $515 Found 1 day ago

Wed, Jul 29 - Tue, Aug 4

OAK

Oakland

ORD

Chicago

CA $545

Roundtrip

Found 5 days ago

Select Alaska Airlines flight, departing Wed, Jul 29 from Oakland to Chicago, returning Tue, Aug 4, priced at CA $545 Found 5 days ago

Thu, Aug 20 - Sun, Aug 23

OAK

Oakland

ORD

Chicago

CA $588

Roundtrip

Found 19 hours ago

Select Alaska Airlines flight, departing Thu, Aug 20 from Oakland to Chicago, returning Sun, Aug 23, priced at CA $588 Found 19 hours ago

Thu, Aug 27 - Sun, Aug 30

OAK

Oakland

ORD

Chicago

CA $598

Roundtrip

Found 1 day ago

Select Alaska Airlines flight, departing Thu, Aug 27 from Oakland to Chicago, returning Sun, Aug 30, priced at CA $598 Found 1 day ago

Wed, Jul 29 - Tue, Aug 4

OAK

Oakland

ORD

Chicago

CA $607

Roundtrip

Found 5 days ago

Select Delta flight, departing Wed, Jul 29 from Oakland to Chicago, returning Tue, Aug 4, priced at CA $607 Found 5 days ago

Thu, Aug 20 - Sun, Aug 23

OAK

Oakland

ORD

Chicago

CA $622

Roundtrip

Found 19 hours ago

Select Alaska Airlines flight, departing Thu, Aug 20 from Oakland to Chicago, returning Sun, Aug 23, priced at CA $622 Found 19 hours ago

Wed, Jul 29 - Tue, Aug 4

OAK

Oakland

ORD

Chicago

CA $625

Roundtrip

Found 5 days ago

Select Alaska Airlines flight, departing Wed, Jul 29 from Oakland to Chicago, returning Tue, Aug 4, priced at CA $625 Found 5 days ago

Thu, Aug 27 - Sun, Aug 30

OAK

Oakland

ORD

Chicago

CA $629

Roundtrip

Found 1 day ago

Select Alaska Airlines flight, departing Thu, Aug 27 from Oakland to Chicago, returning Sun, Aug 30, priced at CA $629 Found 1 day ago

Wed, Jul 29 - Tue, Aug 4

OAK

Oakland

ORD

Chicago

CA $630

Roundtrip

Found 3 days ago

Select Alaska Airlines flight, departing Wed, Jul 29 from Oakland to Chicago, returning Tue, Aug 4, priced at CA $630 Found 3 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $653

ORD

O'Hare Intl.

Cheapest

23 min

Flights from CA $653

Find the cheapest month to fly from Oakland (OAK) to Chicago (CHI)

April is typically the cheapest month to fly

From CA $270 - CA $880 per traveller.

Travel information

Origin airport	Oakland Intl. Airport
Destination airport	Chicago O'Hare International Airport
Distance	2,946 km away
Airlines serving	Alaska Airlines, Delta, Frontier Airlines
Popular airline	Alaska Airlines
Roundtrip price	CA $504

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

Popular airlines from Oakland Intl. Airport (OAK) to Chicago

Be in the know

Book smarter

Earn twice

Cheap Flights from Oakland to Chicago (OAK-CHI)

Alternative airports near Chicago

Find the cheapest month to fly from Oakland (OAK) to Chicago (CHI)

April is typically the cheapest month to flyApril is typically the cheapest month to fly

Travel information

Explore a world of travel with Expedia

April is typically the cheapest month to fly