$74 Cheap flight deals from Chicago (CHI) to Los Gatos (SJC)

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This Weekend's Flight Deals from Chicago to Los Gatos

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, Dec 27 - Wed, Dec 31
MDW
Midway Intl.
SFO
San Francisco Intl.
$410 Roundtrip, found 11 hours ago
$410
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sat, Dec 27 from Midway Intl. to San Francisco Intl., returning Wed, Dec 31, priced at $410 found 11 hours ago
Fri, Dec 26 - Wed, Dec 31
RFD
Greater Rockford
SFO
San Francisco Intl.
$494 Roundtrip, found 2 days ago
$494
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Dec 26 from Greater Rockford to San Francisco Intl., returning Wed, Dec 31, priced at $494 found 2 days ago
Fri, Dec 26 - Tue, Dec 30
MDW
Midway Intl.
SJC
Norman Y. Mineta San Jose Intl.
$611 Roundtrip, found 5 days ago
$611
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Dec 26 from Midway Intl. to Norman Y. Mineta San Jose Intl., returning Tue, Dec 30, priced at $611 found 5 days ago
Sun, Dec 28 - Tue, Dec 30
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$614 Roundtrip, found 1 hour ago
$614
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, Dec 28 from O'Hare Intl. to San Francisco Intl., returning Tue, Dec 30, priced at $614 found 1 hour ago

Airfares from $74 One Way, $110 Round Trip from Chicago to Los Gatos

Prices starting at $110 for return flights and $74 for one-way flights to Los Gatos were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Feb 10 - Tue, Feb 17
ORD
Chicago
SFO
San Francisco
$110 Roundtrip, found 5 days ago
$110
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Chicago to San Francisco, returning Tue, Feb 17, priced at $110 found 5 days ago
Sat, Jan 10 - Mon, Jan 12
MDW
Chicago
SFO
San Francisco
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Chicago to San Francisco, returning Mon, Jan 12, priced at $184 found 2 days ago
Tue, Jan 13 - Thu, Jan 15
ORD
Chicago
SJC
San Jose
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Jan 13 from Chicago to San Jose, returning Thu, Jan 15, priced at $222 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
SFO
San Francisco
$223 Roundtrip, found 9 hours ago
$223
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sat, Jan 17 from Chicago to San Francisco, returning Tue, Jan 20, priced at $223 found 9 hours ago
Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
SFO
San Francisco
$232 Roundtrip, found 9 hours ago
$232
Roundtrip
found 9 hours ago
Select Alaska Airlines flight, departing Sat, Jan 17 from Chicago to San Francisco, returning Tue, Jan 20, priced at $232 found 9 hours ago

Los Gatos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Inn At Union Square
3.5-star property

Inn At Union Square

9.2/10 Wonderful! (1,008 reviews)

Feb 3 - Feb 5

2 night stay

Chicago (CHI) to San Francisco (SFO)

Alaska Airlines • Non-stop • Coach

San Francisco (SFO) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $670, price is now $419 per person
$419
per person
found 1 day ago
The staff here were amazing! So friendly and helpful. Great location right at Union Square… close to many restaurants and lots of shopping options. Breakfast was minimal, but the room was quaint and well supplied. Would definitely stay here again.

Reviewed on Sep 26, 2025

Hotel Riu Plaza Fisherman's Wharf
4.0-star property

Hotel Riu Plaza Fisherman's Wharf

9/10 Wonderful! (7,203 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (CHI) to San Francisco (SFO)

Delta • Non-stop • Coach

San Francisco (SFO) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $720, price is now $484 per person
$484
per person
found 23 hours ago
The hotel is very clean and comfortable. The location is excellent. The breakfast is varied and plentiful. The staff were kind and helpful.

Reviewed on Dec 5, 2025

Treehouse Hotel Silicon Valley
5.0-star property

Treehouse Hotel Silicon Valley

9.6/10 Exceptional! (59 reviews)

Feb 5 - Feb 8

3 night stay

Chicago (CHI) to San Francisco (SFO)

Delta • Non-stop • Coach

San Francisco (SFO) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $3,789, price is now $2,601 per person
$2,601
per person
found 15 hours ago
Such a wonderful place to stay ; the pool is awesome !

Reviewed on Jul 28, 2025

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Los Gatos first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Phoenix Hotel
3.0-star property

The Phoenix Hotel

9/10 Wonderful! (1,004 reviews)

Feb 10 - Feb 17

7 night stay

Chicago (ORD) to San Francisco (SFO)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $1,454, price is now $1,062 per person
$1,062
per person
found 1 day ago
LOVED the Phoenix! Awesome staff, fun themed hotel. It’s an oasis in the center of SF. I’d love to stay there again! Full of personality and character.

Reviewed on Nov 24, 2024

Hotel Riu Plaza Fisherman's Wharf
4.0-star property

Hotel Riu Plaza Fisherman's Wharf

9/10 Wonderful! (7,203 reviews)

Feb 10 - Feb 17

7 night stay

Chicago (ORD) to San Francisco (SFO)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $1,636, price is now $1,155 per person
$1,155
per person
found 1 day ago
The hotel is very clean and comfortable. The location is excellent. The breakfast is varied and plentiful. The staff were kind and helpful.

Reviewed on Dec 5, 2025

Bay Landing San Francisco Airport Hotel
3.0-star property

Bay Landing San Francisco Airport Hotel

9/10 Wonderful! (4,699 reviews)

Feb 10 - Feb 17

7 night stay

Chicago (ORD) to San Francisco (SFO)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $1,605, price is now $1,158 per person
$1,158
per person
found 1 day ago
The room was spotless. Beautiful hotel.

Reviewed on Nov 3, 2025

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More About Flying To Los Gatos from Chicago

Route Information for Flights from Chicago to Los Gatos

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

Chicago to Los Gatos

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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.