$59 Cheap flight deals from Portland (PDX) to Gilroy (SJC)

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This Weekend's Flight Deals from Portland to Gilroy

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.

Sun, Nov 16 - Thu, Nov 20
PDX
Portland Intl.
SJC
Norman Y. Mineta San Jose Intl.
$302 Roundtrip, found 5 days ago
$302
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Sun, Nov 16 from Portland Intl. to Norman Y. Mineta San Jose Intl., returning Thu, Nov 20, priced at $302 found 5 days ago
Sat, Nov 15 - Tue, Dec 2
PDX
Portland Intl.
MRY
Monterey Peninsula
$306 Roundtrip, found 3 hours ago
$306
Roundtrip
found 3 hours ago
Select Hawaiian Airlines flight, departing Sat, Nov 15 from Portland Intl. to Monterey Peninsula, returning Tue, Dec 2, priced at $306 found 3 hours ago

Airfares from $59 One Way, $117 Round Trip from Portland to Gilroy

Prices starting at $117 for return flights and $59 for one-way flights to Gilroy 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
PDX
Portland
SJC
San Jose
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Feb 10 from Portland to San Jose, returning Tue, Feb 17, priced at $117 found 2 days ago
Tue, Feb 10 - Tue, Feb 17
PDX
Portland
SJC
San Jose
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Feb 10 from Portland to San Jose, returning Tue, Feb 17, priced at $127 found 2 days ago
Tue, Feb 10 - Tue, Feb 17
PDX
Portland
SJC
San Jose
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Feb 10 from Portland to San Jose, returning Tue, Feb 17, priced at $137 found 2 days ago
Wed, Jan 21 - Mon, Jan 26
PDX
Portland
SJC
San Jose
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jan 21 from Portland to San Jose, returning Mon, Jan 26, priced at $178 found 2 days ago
Wed, Feb 11 - Wed, Feb 18
PDX
Portland
MRY
Monterey
$182 Roundtrip, found 6 days ago
$182
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Wed, Feb 11 from Portland to Monterey, returning Wed, Feb 18, priced at $182 found 6 days ago

Gilroy economy flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton San Jose
4.0-star property

DoubleTree by Hilton San Jose

7.2/10 Good! (1,008 reviews)

Dec 28 - Jan 1

4 night stay

Portland (PDX) to San Jose (SJC)

Southwest Airlines • Coach

San Jose (SJC) to Portland (PDX)

Alaska Airlines • Coach
Price was $521, price is now $342 per person
$342
per person
found 1 day ago
Great service at the front desk, shuttle drivers and breakfast buffet staff I didn’t see or use hotel amenities but the room itself was a little shabby. Worn carpet, crusty shower head and old worn furniture The shower was in a bathtub that was poorly caulked and slow draining and not very good water pressure. Not what I expected for $200/ night

Reviewed on Sep 21, 2025

Juniper Hotel Cupertino, Curio Collection by Hilton
4.0-star property

Juniper Hotel Cupertino, Curio Collection by Hilton

9/10 Wonderful! (1,008 reviews)

Dec 28 - Jan 1

4 night stay

Portland (PDX) to San Jose (SJC)

Southwest Airlines • Coach

San Jose (SJC) to Portland (PDX)

Alaska Airlines • Coach
Price was $537, price is now $397 per person
$397
per person
found 1 day ago
Staff not very attentive or helpful

Reviewed on Jan 11, 2025

Sonesta Silicon Valley
4.0-star property

Sonesta Silicon Valley

9/10 Wonderful! (1,634 reviews)

Dec 28 - Jan 1

4 night stay

Portland (PDX) to San Jose (SJC)

Southwest Airlines • Coach

San Jose (SJC) to Portland (PDX)

Alaska Airlines • Coach
Price was $473, price is now $359 per person
$359
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

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More About Flying To Gilroy from Portland

Route Information for Flights from Portland to Gilroy

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

Portland to Gilroy

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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.