Flights from Chicago to Guerneville

Cheapest flights from Chicago

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.

Sat, Aug 2 - Sat, Aug 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$175 Roundtrip, found 2 days ago

$175

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Oakland Intl., returning Sat, Aug 9, priced at $175 found 2 days ago

Fri, Aug 8 - Sat, Aug 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$182 Roundtrip, found 2 days ago

$182

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Oakland Intl., returning Sat, Aug 9, priced at $182 found 2 days ago

Tue, Aug 5 - Mon, Aug 11

ORD

O'Hare Intl.

OAK

Oakland Intl.

$194 Roundtrip, found 2 days ago

$194

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Oakland Intl., returning Mon, Aug 11, priced at $194 found 2 days ago

Tue, Sep 9 - Tue, Sep 16

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$197 Roundtrip, found 5 days ago

$197

Roundtrip

found 5 days ago

Select United flight, departing Tue, Sep 9 from O'Hare Intl. to San Francisco Intl., returning Tue, Sep 16, priced at $197 found 5 days ago

Tue, Aug 19 - Tue, Aug 19

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$197 Roundtrip, found 4 hours ago

$197

Roundtrip

found 4 hours ago

Select United flight, departing Tue, Aug 19 from O'Hare Intl. to San Francisco Intl., returning Tue, Aug 19, priced at $197 found 4 hours ago

Tue, Aug 19 - Tue, Aug 19

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$197 Roundtrip, found 4 hours ago

$197

Roundtrip

found 4 hours ago

Select American Airlines flight, departing Tue, Aug 19 from O'Hare Intl. to San Francisco Intl., returning Tue, Aug 19, priced at $197 found 4 hours ago

Thu, Aug 7 - Tue, Aug 12

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$207 Roundtrip, found 22 hours ago

$207

Roundtrip

found 22 hours ago

Select Hawaiian Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to San Francisco Intl., returning Tue, Aug 12, priced at $207 found 22 hours ago

Thu, Aug 7 - Wed, Aug 13

MDW

Midway Intl.

SFO

San Francisco Intl.

$208 Roundtrip, found 22 hours ago

$208

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Thu, Aug 7 from Midway Intl. to San Francisco Intl., returning Wed, Aug 13, priced at $208 found 22 hours ago

Mon, Sep 22 - Sat, Sep 27

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$210 Roundtrip, found 1 day ago

$210

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to San Francisco Intl., returning Sat, Sep 27, priced at $210 found 1 day ago

Sat, Aug 2 - Fri, Aug 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$211 Roundtrip, found 2 days ago

$211

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Oakland Intl., returning Fri, Aug 8, priced at $211 found 2 days ago

Thu, Aug 7 - Sat, Aug 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$213 Roundtrip, found 2 days ago

$213

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to Oakland Intl., returning Sat, Aug 9, priced at $213 found 2 days ago

Fri, Sep 26 - Sat, Sep 27

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$214 Roundtrip, found 1 day ago

$214

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Sep 26 from O'Hare Intl. to San Francisco Intl., returning Sat, Sep 27, priced at $214 found 1 day ago

Thu, Aug 7 - Thu, Aug 14

MDW

Midway Intl.

SFO

San Francisco Intl.

$215 Roundtrip, found 22 hours ago

$215

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Thu, Aug 7 from Midway Intl. to San Francisco Intl., returning Thu, Aug 14, priced at $215 found 22 hours ago

Thu, Sep 25 - Mon, Sep 29

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$216 Roundtrip, found 1 day ago

$216

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Sep 25 from O'Hare Intl. to San Francisco Intl., returning Mon, Sep 29, priced at $216 found 1 day ago

Tue, Jul 29 - Mon, Aug 18

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$217 Roundtrip, found 4 hours ago

$217

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to San Francisco Intl., returning Mon, Aug 18, priced at $217 found 4 hours ago

Thu, Aug 7 - Sat, Aug 16

MDW

Midway Intl.

SFO

San Francisco Intl.

$219 Roundtrip, found 22 hours ago

$219

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Thu, Aug 7 from Midway Intl. to San Francisco Intl., returning Sat, Aug 16, priced at $219 found 22 hours ago

Tue, Aug 19 - Tue, Aug 19

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$231 Roundtrip, found 4 hours ago

$231

Roundtrip

found 4 hours ago

Select Alaska Airlines flight, departing Tue, Aug 19 from O'Hare Intl. to San Francisco Intl., returning Tue, Aug 19, priced at $231 found 4 hours ago

Tue, Jul 29 - Sun, Aug 17

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$257 Roundtrip, found 4 hours ago

$257

Roundtrip

found 4 hours ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to San Francisco Intl., returning Sun, Aug 17, priced at $257 found 4 hours ago

Tue, Sep 9 - Tue, Sep 16

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$383 Roundtrip, found 5 days ago

$383

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, Sep 9 from O'Hare Intl. to San Francisco Intl., returning Tue, Sep 16, priced at $383 found 5 days ago

Tue, Aug 5 - Sat, Aug 16

MDW

Midway Intl.

OAK

Oakland Intl.

$478 Roundtrip, found 22 hours ago

$478

Roundtrip

found 22 hours ago

Select Delta flight, departing Tue, Aug 5 from Midway Intl. to Oakland Intl., returning Sat, Aug 16, priced at $478 found 22 hours ago