$79 Cheap flight deals from Chicago (CHI) to Guerneville (OAK)

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This Weekend's Flight Deals from Chicago to Guerneville

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 9 - Mon, Jan 12
MDW
Midway Intl.
SFO
San Francisco Intl.
$220 Roundtrip, found 6 days ago
$220
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Midway Intl. to San Francisco Intl., returning Mon, Jan 12, priced at $220 found 6 days ago
Sat, Jan 10 - Wed, Jan 14
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$233 Roundtrip, just found
$233
Roundtrip
just found
Select Bargain Flight flight, departing Sat, Jan 10 from O'Hare Intl. to San Francisco Intl., returning Wed, Jan 14, priced at $233 just found
Fri, Jan 9 - Mon, Jan 12
ORD
O'Hare Intl.
OAK
Oakland Intl.
$374 Roundtrip, found 23 hours ago
$374
Roundtrip
found 23 hours ago
Select Bargain Flight flight, departing Fri, Jan 9 from O'Hare Intl. to Oakland Intl., returning Mon, Jan 12, priced at $374 found 23 hours ago
Fri, Jan 9 - Wed, Jan 14
MDW
Midway Intl.
OAK
Oakland Intl.
$499 Roundtrip, found 16 hours ago
$499
Roundtrip
found 16 hours ago
Select Delta flight, departing Fri, Jan 9 from Midway Intl. to Oakland Intl., returning Wed, Jan 14, priced at $499 found 16 hours ago

Airfares from $79 One Way, $148 Round Trip from Chicago to Guerneville

Prices starting at $148 for return flights and $79 for one-way flights to Guerneville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 11 - Wed, Feb 18
ORD
Chicago
SFO
San Francisco
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 11 from Chicago to San Francisco, returning Wed, Feb 18, priced at $148 found 1 day ago
Thu, Feb 12 - Mon, Feb 23
MDW
Chicago
SFO
San Francisco
$182 Roundtrip, found 6 days ago
$182
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Feb 12 from Chicago to San Francisco, returning Mon, Feb 23, priced at $182 found 6 days ago
Sat, Jan 17 - Wed, Jan 21
ORD
Chicago
SFO
San Francisco
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Jan 17 from Chicago to San Francisco, returning Wed, Jan 21, priced at $221 found 1 day ago
Sat, Jan 17 - Tue, Jan 20
RFD
Rockford
SFO
San Francisco
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 17 from Rockford to San Francisco, returning Tue, Jan 20, priced at $222 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
SFO
San Francisco
$223 Roundtrip, found 6 hours ago
$223
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Jan 17 from Chicago to San Francisco, returning Tue, Jan 20, priced at $223 found 6 hours ago

Guerneville economy flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Berkeley Marina
4.0-star property

DoubleTree by Hilton Hotel Berkeley Marina

8.2/10 Very Good! (3,745 reviews)

Feb 19 - Feb 24

5 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $646, price is now $384 per person
$384
per person
found 1 day ago
Noisy- the laundry machine was running the whole evening

Reviewed on Nov 10, 2025

Claremont Resort & Club
5.0-star property

Claremont Resort & Club

8.8/10 Excellent! (1,003 reviews)

Feb 19 - Feb 24

5 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,216, price is now $671 per person
$671
per person
found 1 day ago
50$/night facility fee is charged for every night I stayed there. This was not clear to me at the time of booking. Overall a good hotel.

Reviewed on May 25, 2024

Montage Healdsburg
5.0-star property

Montage Healdsburg

9.6/10 Exceptional! (113 reviews)

Feb 12 - Feb 15

3 night stay

Chicago (ORD) to San Francisco (SFO)

Southwest Airlines • Non-stop • Coach

San Francisco (SFO) to Chicago (ORD)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,164, price is now $1,293 per person
$1,293
per person
found 1 day ago
Very peaceful, excellent service. Top notch

Reviewed on Jul 11, 2024

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More About Flying To Guerneville from Chicago

Route Information for Flights from Chicago to Guerneville

Origin Airport IATA Code
CHI
Destination Airport IATA Code
OAK
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Guerneville

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.