$103 Cheap flight deals from Chicago (CHI) to San Anselmo (OAK)

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This Weekend's Flight Deals from Chicago to San Anselmo

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.

Sat, Jun 13 - Mon, Jun 15
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$348 Roundtrip, found 10 hours ago
$348
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Jun 13 from O'Hare Intl. to San Francisco Intl., returning Mon, Jun 15, priced at $348 found 10 hours ago
Fri, Jun 12 - Sun, Jun 14
MDW
Midway Intl.
SFO
San Francisco Intl.
$381 Roundtrip, found 3 days ago
$381
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jun 12 from Midway Intl. to San Francisco Intl., returning Sun, Jun 14, priced at $381 found 3 days ago
Fri, Jun 12 - Mon, Jun 15
ORD
O'Hare Intl.
OAK
Oakland Intl.
$460 Roundtrip, found 5 days ago
$460
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Fri, Jun 12 from O'Hare Intl. to Oakland Intl., returning Mon, Jun 15, priced at $460 found 5 days ago
Sat, Jun 13 - Sat, Jun 20
MDW
Midway Intl.
OAK
Oakland Intl.
$494 Roundtrip, found 1 day ago
$494
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jun 13 from Midway Intl. to Oakland Intl., returning Sat, Jun 20, priced at $494 found 1 day ago

Airfares from $103 One Way, $223 Round Trip from Chicago to San Anselmo

Prices starting at $223 for return flights and $103 for one-way flights to San Anselmo were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 6 - Wed, Aug 12
MDW
Chicago
SFO
San Francisco
$223 Roundtrip, found 4 days ago
$223
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Chicago to San Francisco, returning Wed, Aug 12, priced at $223 found 4 days ago
Thu, Aug 6 - Sat, Aug 8
ORD
Chicago
SFO
San Francisco
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Chicago to San Francisco, returning Sat, Aug 8, priced at $225 found 4 days ago
Wed, Nov 11 - Mon, Nov 16
ORD
Chicago
SFO
San Francisco
$247 Roundtrip, found 7 hours ago
$247
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Wed, Nov 11 from Chicago to San Francisco, returning Mon, Nov 16, priced at $247 found 7 hours ago
Wed, Nov 4 - Tue, Nov 10
RFD
Rockford
SFO
San Francisco
$253 Roundtrip, found 2 days ago
$253
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Nov 4 from Rockford to San Francisco, returning Tue, Nov 10, priced at $253 found 2 days ago
Wed, Jul 1 - Tue, Jul 7
ORD
Chicago
SFO
San Francisco
$253 Roundtrip, found 15 hours ago
$253
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Wed, Jul 1 from Chicago to San Francisco, returning Tue, Jul 7, priced at $253 found 15 hours ago

San Anselmo economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Nest Hotel Palo Alto
3.5-star property

The Nest Hotel Palo Alto

8.8/10 Excellent! (1,003 reviews)

Jul 13 - Jul 21

8 night stay

Chicago (CHI) to San Francisco (SFO)

Alaska Airlines • Non-stop • Coach

San Francisco (SFO) to Chicago (CHI)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,659, price is now $1,036 per person
$1,036
per person
found 10 hours ago
The place is convenient and the room comes with delicious breakfast: potatoes, eggs, chicken sausages, English muffins, bagels, sliced bread, muffins, fresh fruit, orange juice, tea, and coffee.

Reviewed on Apr 19, 2026

Creekside Inn
3.5-star property

Creekside Inn

9/10 Wonderful! (1,804 reviews)

Jul 13 - Jul 21

8 night stay

Chicago (CHI) to San Francisco (SFO)

Alaska Airlines • Non-stop • Coach

San Francisco (SFO) to Chicago (CHI)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,760, price is now $1,172 per person
$1,172
per person
found 9 hours ago
would recommend to anyone who wants to stay in the area

Reviewed on Aug 1, 2025

Hyatt Regency Monterey Hotel & Spa
4.5-star property

Hyatt Regency Monterey Hotel & Spa

8.6/10 Excellent! (1,636 reviews)

Jul 21 - Jul 28

7 night stay

Chicago (CHI) to San Francisco (SFO)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,526, price is now $1,791 per person
$1,791
per person
found 1 day ago
The front desk staff was extremely helpful and answered any questions we had about things to enjoy in the area! Our room was clean and pool was so nice, it is 8 feet deep and heated. We did not get a chance to check out the sauna and steam room, but works. I had to learn that they had those options as well. It is a very well kept property hidden behind the tree line from the main road, creating a scenic experience.

Reviewed on Jun 5, 2026

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More About Flying To San Anselmo from Chicago

Route Information for Flights from Chicago to San Anselmo

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

Chicago to San Anselmo

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Best Deals At Your Fingertips

Orbitz combines low prices on Chicago to San Anselmo flights with discounts on quality hotels. Using Orbitz’s Display Matrix, you can see all your options and savings easily. With our low price guarantee, you know you have the best deals at your fingertips.

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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.