$69 Cheap flight deals from Portland (PDX) to Windsor (OAK)

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This Weekend's Flight Deals from Portland to Windsor

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, May 2 - Mon, May 4
PDX
Portland Intl.
OAK
Oakland Intl.
$311 Roundtrip, found 6 days ago
$311
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Sat, May 2 from Portland Intl. to Oakland Intl., returning Mon, May 4, priced at $311 found 6 days ago
Sun, May 3 - Wed, May 6
PDX
Portland Intl.
STS
Sonoma County
$423 Roundtrip, found 1 day ago
$423
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sun, May 3 from Portland Intl. to Sonoma County, returning Wed, May 6, priced at $423 found 1 day ago

Airfares from $69 One Way, $137 Round Trip from Portland to Windsor

Prices starting at $137 for return flights and $69 for one-way flights to Windsor were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 12 - Wed, Aug 19
PDX
Portland
OAK
Oakland
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Wed, Aug 12 from Portland to Oakland, returning Wed, Aug 19, priced at $137 found 1 hour ago
Sat, May 30 - Tue, Jun 2
PDX
Portland
OAK
Oakland
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, May 30 from Portland to Oakland, returning Tue, Jun 2, priced at $140 found 6 days ago
Tue, Jun 9 - Tue, Jun 16
PDX
Portland
OAK
Oakland
$140 Roundtrip, found 6 hours ago
$140
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Portland to Oakland, returning Tue, Jun 16, priced at $140 found 6 hours ago
Sat, May 30 - Tue, Jun 2
PDX
Portland
OAK
Oakland
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, May 30 from Portland to Oakland, returning Tue, Jun 2, priced at $143 found 6 days ago
Wed, Aug 12 - Wed, Aug 19
PDX
Portland
OAK
Oakland
$147 Roundtrip, found 1 hour ago
$147
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Aug 12 from Portland to Oakland, returning Wed, Aug 19, priced at $147 found 1 hour ago

Windsor economy flight packages

Price found within the past 48 hours. Click for updated prices.
Claremont Resort & Club
5.0-star property

Claremont Resort & Club

9/10 Wonderful! (1,005 reviews)

Jun 11 - Jun 14

3 night stay

Portland (PDX) to Oakland (OAK)

Alaska Airlines • Coach

Oakland (OAK) to Portland (PDX)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,014, price is now $722 per person
$722
per person
found 1 day ago
50$/night facility fee is charged for every night I stayed there. This was not clear to me at the time of booking. Overall a good hotel.

Reviewed on May 25, 2024

Bardessono Hotel and Spa
5.0-star property

Bardessono Hotel and Spa

9.8/10 Exceptional! (681 reviews)

Jun 17 - Jun 19

2 night stay

Portland (PDX) to Oakland (OAK)

Alaska Airlines • Coach

Oakland (OAK) to Portland (PDX)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,919, price is now $1,366 per person
$1,366
per person
found 1 day ago
Fantastic hotel and location. Rooms are very nice and the hotel grounds are excellent.

Reviewed on Jun 28, 2025

Solage, Auberge Collection
5.0-star property

Solage, Auberge Collection

9.6/10 Exceptional! (713 reviews)

Jun 17 - Jun 19

2 night stay

Portland (PDX) to Oakland (OAK)

Alaska Airlines • Coach

Oakland (OAK) to Portland (PDX)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,499, price is now $1,092 per person
$1,092
per person
found 1 day ago
We have been going to Solage since 2010. Back then it was the nicest property in Calistoga. The problem is that that management has upgraded since 2010, or so it feels like. Pros are the following: 1. Property is still manicured well with staff on site ensuring both cleanliness and aesthetic. 2. Spa is still pretty nice. 3. Service was solid, overall..not the best but still in the top 10-15% of hotels. Cons: 1. Property has not been remodeled in some time and it shows. While it’s well maintained, the technology is nonexistent and quite frankly outdated; 2. Solbar does not deserve a Michelin recommendation or star. It was so disappointing. For starters the bacon was clearly thrown in the deep fryer, not cooked on the griddled. The smashed potatoes they are known for weren’t crispy and it appeared as though the oil wasn’t changed for many days. The fruit bowl was clunky. If I’m paying $16.00 for a fruit bowl, you should take the time and peel the fruit, present it nicely and make it beautiful. It was not that, just thrown together with little to no care. Dining room was load with kids. This is supposed to be a relaxing retreat not kids running around like Disneyland. If I wanted that experience I would go to the OC. Needless to say I did not enjoy paying $150 for breakfast and have such an awful experience. 3. A few more comments on the room and being outdated and old. The property is pretty dingy. The common areas are not well maintained.

Reviewed on Dec 25, 2025

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More About Flying To Windsor from Portland

Route Information for Flights from Portland to Windsor

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

Portland to Windsor

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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.