$75 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.

Fri, Oct 9 - Tue, Oct 13
MDW
Midway Intl.
SFO
San Francisco Intl.
$318 Roundtrip, found 20 hours ago
$318
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, Oct 9 from Midway Intl. to San Francisco Intl., returning Tue, Oct 13, priced at $318 found 20 hours ago
Fri, Oct 9 - Mon, Oct 26
ORD
O'Hare Intl.
OAK
Oakland Intl.
$416 Roundtrip, found 16 hours ago
$416
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Fri, Oct 9 from O'Hare Intl. to Oakland Intl., returning Mon, Oct 26, priced at $416 found 16 hours ago
Sun, Oct 11 - Sat, Oct 17
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$417 Roundtrip, found 1 hour ago
$417
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Oct 11 from O'Hare Intl. to San Francisco Intl., returning Sat, Oct 17, priced at $417 found 1 hour ago
Sun, Oct 11 - Thu, Oct 15
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$523 Roundtrip, found 1 day ago
$523
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Oct 11 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Thu, Oct 15, priced at $523 found 1 day ago

Airfares from $75 One Way, $157 Round Trip from Chicago to Pescadero

Prices starting at $157 for return flights and $75 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.

Tue, Nov 24 - Sat, Dec 5
ORD
Chicago
SFO
San Francisco
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Nov 24 from Chicago to San Francisco, returning Sat, Dec 5, priced at $157 found 1 hour ago
Fri, Nov 6 - Mon, Nov 9
ORD
Chicago
OAK
Oakland
$201 Roundtrip, found 15 hours ago
$201
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Fri, Nov 6 from Chicago to Oakland, returning Mon, Nov 9, priced at $201 found 15 hours ago
Mon, Feb 22 - Mon, Mar 1
ORD
Chicago
SJC
San Jose
$201 Roundtrip, found 4 hours ago
$201
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Feb 22 from Chicago to San Jose, returning Mon, Mar 1, priced at $201 found 4 hours ago
Mon, Dec 7 - Thu, Dec 10
ORD
Chicago
SFO
San Francisco
$231 Roundtrip, found 1 hour ago
$231
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Mon, Dec 7 from Chicago to San Francisco, returning Thu, Dec 10, priced at $231 found 1 hour ago
Mon, Dec 7 - Thu, Dec 10
ORD
Chicago
SFO
San Francisco
$231 Roundtrip, found 1 hour ago
$231
Roundtrip
found 1 hour ago
Select United flight, departing Mon, Dec 7 from Chicago to San Francisco, returning Thu, Dec 10, priced at $231 found 1 hour ago

Pescadero economy flight packages

Price found within the past 48 hours. Click for updated prices.
Shashi Hotel Mountain View Palo Alto
5.0-star property

Shashi Hotel Mountain View Palo Alto

9.4/10 Exceptional! (1,458 reviews)

Nov 12 - Nov 15

3 night stay

Chicago (CHI) to San Jose (SJC)

Southwest Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Price was $923, price is now $695 per person
$695
per person
found 1 day ago
I had heard lovely reviews of this place, especially if you're seeing a show at Shoreline Amphitheater. I agree with the recommendations. It is close to the venue with an easy walk, the amenities are nice, and the place is incredibly clean. The only reason I wouldn't give it a perfect score is because upon arriving and checking in, I noticed other guests being given a complimentary beverage of either champagne/sparkling wine, or a beer. Myself and the other guests are all over 21, and I even presented my ID during the check-in process, but none of us were offered this amenity, seemingly due to being assumed "too-young." I understand maybe questioning us and asking for our IDs, but to not be offered anything at all made us feel a bit bummed out at how we were being seen and treated differently than the other guests.

Reviewed on Oct 5, 2026

La Bahia Hotel and Spa
4.5-star property

La Bahia Hotel and Spa

9.6/10 Exceptional! (527 reviews)

Nov 7 - Nov 13

6 night stay

Chicago (ORD) to San Jose (SJC)

American Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,855, price is now $1,234 per person
$1,234
per person
found 17 hours ago

Aqua Breeze Inn
2.5-star property

Aqua Breeze Inn

8.2/10 Very Good! (1,002 reviews)

Nov 7 - Nov 13

6 night stay

Chicago (ORD) to San Jose (SJC)

American Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach
Price was $988, price is now $701 per person
$701
per person
found 17 hours 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.