$70 Cheap flight deals from Chicago (CHI) to Pescadero (SJC)

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This Weekend's Flight Deals from Chicago to Pescadero

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, Nov 15 - Sun, Dec 7
MDW
Midway Intl.
SFO
San Francisco Intl.
$223 Roundtrip, found 16 hours ago
$223
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Midway Intl. to San Francisco Intl., returning Sun, Dec 7, priced at $223 found 16 hours ago
Fri, Nov 14 - Mon, Nov 17
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$402 Roundtrip, just found
$402
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to San Francisco Intl., returning Mon, Nov 17, priced at $402 just found
Sat, Nov 15 - Sat, Nov 15
ORD
O'Hare Intl.
OAK
Oakland Intl.
$480 Roundtrip, found 6 days ago
$480
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to Oakland Intl., returning Sat, Nov 15, priced at $480 found 6 days ago
Sat, Nov 15 - Tue, Nov 18
RFD
Greater Rockford
SFO
San Francisco Intl.
$657 Roundtrip, found 6 days ago
$657
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Nov 15 from Greater Rockford to San Francisco Intl., returning Tue, Nov 18, priced at $657 found 6 days ago

Airfares from $70 One Way, $140 Round Trip from Chicago to Pescadero

Prices starting at $140 for return flights and $70 for one-way flights to Pescadero were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jan 12 - Thu, Jan 22
ORD
Chicago
SFO
San Francisco
$140 Roundtrip, found 1 hour ago
$140
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Jan 12 from Chicago to San Francisco, returning Thu, Jan 22, priced at $140 found 1 hour ago
Thu, Jan 8 - Mon, Jan 12
MDW
Chicago
SFO
San Francisco
$142 Roundtrip, found 10 hours ago
$142
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Chicago to San Francisco, returning Mon, Jan 12, priced at $142 found 10 hours ago
Mon, Dec 15 - Thu, Jan 8
ORD
Chicago
SJC
San Jose
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Mon, Dec 15 from Chicago to San Jose, returning Thu, Jan 8, priced at $204 found 5 days ago
Tue, Dec 16 - Wed, Dec 17
ORD
Chicago
SFO
San Francisco
$221 Roundtrip, found 12 hours ago
$221
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Chicago to San Francisco, returning Wed, Dec 17, priced at $221 found 12 hours ago
Wed, Jan 7 - Tue, Jan 27
ORD
Chicago
SJC
San Jose
$222 Roundtrip, found 4 days ago
$222
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 7 from Chicago to San Jose, returning Tue, Jan 27, priced at $222 found 4 days ago

Pescadero economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Silicon Valley
4.0-star property

Sonesta Silicon Valley

9/10 Wonderful! (1,634 reviews)

Dec 30 - Jan 4

5 night stay

Chicago (CHI) to San Jose (SJC)

United • Coach

San Jose (SJC) to Chicago (CHI)

Alaska Airlines • Coach
Price was $717, price is now $564 per person
$564
per person
found 1 day ago
This was a nice property. The staff were pleasant and the check in was quick. The bed was good and the sheets were nice. The grounds and lobby were clean, the restaurant was nice and the food was decent (unfortunately, no free breakfast as it appeared on orbitz site). I would give this place a 7 (not a a 9.0 Wonderful rating like Orbitz has listed). No room cleaning and we were there 4 nights (not a huge deal, but we had to take our own garbage and ask for new towels). The pool and hot tub were both dirty. The hot tub was out of chemical balance and the pool needed the skimmer fixed. The prorperty is under construction, but they did shut down by 6pm which was fine for us. It was super loud at check in on a Thursday and if we weren't staying mostly over a weekend we would have been pretty frustrated.

Reviewed on Oct 11, 2025

Shashi Hotel Mountain View Palo Alto
5.0-star property

Shashi Hotel Mountain View Palo Alto

9.4/10 Exceptional! (1,078 reviews)

Dec 30 - Jan 4

5 night stay

Chicago (CHI) to San Jose (SJC)

United • Coach

San Jose (SJC) to Chicago (CHI)

Alaska Airlines • Coach
Price was $800, price is now $640 per person
$640
per person
found 1 day ago
Good facilities like steam room and sauna

Reviewed on Sep 20, 2025

@ Marbella Lane - Modern 3broasis in Siliconvalley
3.0-star property

@ Marbella Lane - Modern 3broasis in Siliconvalley

No reviews

Dec 26 - Dec 29

3 night stay

Chicago (CHI) to San Jose (SJC)

Southwest Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (CHI)

United • Non-stop • Coach
Price was $2,186, price is now $1,766 per person
$1,766
per person
found 1 day ago
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More About Flying To Pescadero from Chicago

Route Information for Flights from Chicago to Pescadero

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

Chicago to Pescadero

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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.