Flights from Oakland to Chicago

Cheapest flights from Oakland

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Aug 5 - Tue, Aug 12

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$188 Roundtrip, found 19 hours ago

$188

Roundtrip

found 19 hours ago

Select Hawaiian Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $188 found 19 hours ago

Wed, Aug 6 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$191 Roundtrip, found 2 days ago

$191

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Wed, Aug 6 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $191 found 2 days ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 19 hours ago

$197

Roundtrip

found 19 hours ago

Select Hawaiian Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $197 found 19 hours ago

Tue, Sep 30 - Tue, Oct 7

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 2 days ago

$197

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $197 found 2 days ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 19 hours ago

$197

Roundtrip

found 19 hours ago

Select United flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $197 found 19 hours ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 19 hours ago

$197

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $197 found 19 hours ago

Sun, Aug 10 - Tue, Aug 12

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$198 Roundtrip, found 5 days ago

$198

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Sun, Aug 10 from San Francisco Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $198 found 5 days ago

Thu, Sep 25 - Sat, Oct 4

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$205 Roundtrip, found 2 days ago

$205

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Sep 25 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sat, Oct 4, priced at $205 found 2 days ago

Tue, Aug 5 - Thu, Aug 7

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$207 Roundtrip, found 19 hours ago

$207

Roundtrip

found 19 hours ago

Select Hawaiian Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $207 found 19 hours ago

Fri, Aug 8 - Sun, Aug 10

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$210 Roundtrip, found 5 days ago

$210

Roundtrip

found 5 days ago

Select American Airlines flight, departing Fri, Aug 8 from San Francisco Intl. to O'Hare Intl., returning Sun, Aug 10, priced at $210 found 5 days ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 19 hours ago

$217

Roundtrip

found 19 hours ago

Select Alaska Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $217 found 19 hours ago

Tue, Sep 30 - Tue, Oct 7

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$224 Roundtrip, found 2 days ago

$224

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $224 found 2 days ago

Fri, Sep 26 - Sat, Oct 4

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 2 days ago

$225

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Sep 26 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sat, Oct 4, priced at $225 found 2 days ago

Tue, Sep 30 - Sun, Oct 5

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$226 Roundtrip, found 4 days ago

$226

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 30 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sun, Oct 5, priced at $226 found 4 days ago

Tue, Sep 30 - Tue, Oct 7

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$228 Roundtrip, found 2 days ago

$228

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $228 found 2 days ago

Sun, Sep 7 - Sun, Sep 14

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$233 Roundtrip, found 2 days ago

$233

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Sep 7 from San Francisco Intl. to O'Hare Intl., returning Sun, Sep 14, priced at $233 found 2 days ago

Fri, Aug 8 - Tue, Aug 12

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$234 Roundtrip, found 19 hours ago

$234

Roundtrip

found 19 hours ago

Select Hawaiian Airlines flight, departing Fri, Aug 8 from San Francisco Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $234 found 19 hours ago

Tue, Sep 9 - Tue, Sep 16

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$236 Roundtrip, found 2 days ago

$236

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Tue, Sep 9 from San Francisco Intl. to O'Hare Intl., returning Tue, Sep 16, priced at $236 found 2 days ago

Sat, Sep 6 - Thu, Sep 11

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$244 Roundtrip, found 2 days ago

$244

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Sep 6 from San Francisco Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $244 found 2 days ago

Sun, Sep 7 - Sun, Sep 14

SFO

San Francisco Intl.

MDW

Midway Intl.

$252 Roundtrip, found 2 days ago

$252

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Sep 7 from San Francisco Intl. to Midway Intl., returning Sun, Sep 14, priced at $252 found 2 days ago