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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 $182 for one-way flights and CA $420 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Thu, Aug 6 - Tue, Aug 18

OAK

Oakland

ORD

Chicago

CA $420

Roundtrip

Found 1 day ago

Select Alaska Airlines flight, departing Thu, Aug 6 from Oakland to Chicago, returning Tue, Aug 18, priced at CA $420 Found 1 day ago

Thu, Aug 6 - Tue, Aug 18

OAK

Oakland

ORD

Chicago

CA $433

Roundtrip

Found 1 day ago

Select Alaska Airlines flight, departing Thu, Aug 6 from Oakland to Chicago, returning Tue, Aug 18, priced at CA $433 Found 1 day ago

Mon, Oct 26 - Mon, Nov 2

OAK

Oakland

ORD

Chicago

CA $438

Roundtrip

Found 2 days ago

Select Alaska Airlines flight, departing Mon, Oct 26 from Oakland to Chicago, returning Mon, Nov 2, priced at CA $438 Found 2 days ago

Fri, Aug 21 - Mon, Aug 24

OAK

Oakland

ORD

Chicago

CA $446

Roundtrip

Found 1 day ago

Select Alaska Airlines flight, departing Fri, Aug 21 from Oakland to Chicago, returning Mon, Aug 24, priced at CA $446 Found 1 day ago

Mon, Oct 26 - Mon, Nov 2

OAK

Oakland

ORD

Chicago

CA $474

Roundtrip

Found 2 days ago

Select Alaska Airlines flight, departing Mon, Oct 26 from Oakland to Chicago, returning Mon, Nov 2, priced at CA $474 Found 2 days ago

Thu, Aug 6 - Tue, Aug 18

OAK

Oakland

ORD

Chicago

CA $476

Roundtrip

Found 1 day ago

Select Alaska Airlines flight, departing Thu, Aug 6 from Oakland to Chicago, returning Tue, Aug 18, priced at CA $476 Found 1 day ago

Sat, Oct 24 - Wed, Oct 28

OAK

Oakland

ORD

Chicago

CA $477

Roundtrip

Found 3 days ago

Select Delta flight, departing Sat, Oct 24 from Oakland to Chicago, returning Wed, Oct 28, priced at CA $477 Found 3 days ago

Sat, Oct 24 - Wed, Oct 28

OAK

Oakland

ORD

Chicago

CA $477

Roundtrip

Found 3 days ago

Select Alaska Airlines flight, departing Sat, Oct 24 from Oakland to Chicago, returning Wed, Oct 28, priced at CA $477 Found 3 days ago

Sat, Oct 24 - Wed, Oct 28

OAK

Oakland

ORD

Chicago

CA $478

Roundtrip

Found 3 days ago

Select Alaska Airlines flight, departing Sat, Oct 24 from Oakland to Chicago, returning Wed, Oct 28, priced at CA $478 Found 3 days ago

Mon, Aug 10 - Tue, Aug 18

OAK

Oakland

ORD

Chicago

CA $485

Roundtrip

Found 3 days ago

Select Alaska Airlines flight, departing Mon, Aug 10 from Oakland to Chicago, returning Tue, Aug 18, priced at CA $485 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 $1,031

ORD

O'Hare Intl.

Cheapest

23 min

Flights from CA $1,031

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 $420

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Flights from Calgary (YYC) to Chicago (CHI)
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Flights from Halifax (YHZ) to Chicago (CHI)
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CA $182 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