$185 Cheap flight deals from Philadelphia (ILG) to Windsor (OAK)

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This Weekend's Flight Deals from Philadelphia 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.

Fri, Jun 5 - Mon, Jun 8
PHL
Philadelphia Intl.
OAK
Oakland Intl.
$618 Roundtrip, found 2 days ago
$618
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jun 5 from Philadelphia Intl. to Oakland Intl., returning Mon, Jun 8, priced at $618 found 2 days ago

Airfares from $185 One Way, $369 Round Trip from Philadelphia to Windsor

Prices starting at $369 for return flights and $185 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.

Thu, Oct 15 - Tue, Oct 20
PHL
Philadelphia
OAK
Oakland
$369 Roundtrip, found 3 days ago
$369
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 15 from Philadelphia to Oakland, returning Tue, Oct 20, priced at $369 found 3 days ago
Sat, Oct 3 - Mon, Oct 5
PHL
Philadelphia
OAK
Oakland
$369 Roundtrip, found 2 days ago
$369
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Sat, Oct 3 from Philadelphia to Oakland, returning Mon, Oct 5, priced at $369 found 2 days ago
Sun, Sep 20 - Mon, Sep 21
PHL
Philadelphia
OAK
Oakland
$374 Roundtrip, found 2 days ago
$374
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Sep 20 from Philadelphia to Oakland, returning Mon, Sep 21, priced at $374 found 2 days ago
Wed, Aug 19 - Wed, Aug 26
PHL
Philadelphia
OAK
Oakland
$377 Roundtrip, found 5 days ago
$377
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Aug 19 from Philadelphia to Oakland, returning Wed, Aug 26, priced at $377 found 5 days ago
Fri, Jul 3 - Fri, Jul 10
PHL
Philadelphia
OAK
Oakland
$377 Roundtrip, found 5 days ago
$377
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Fri, Jul 3 from Philadelphia to Oakland, returning Fri, Jul 10, priced at $377 found 5 days ago

Windsor economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Sonoma Mission Inn & Spa
4.0-star property

Fairmont Sonoma Mission Inn & Spa

8.6/10 Excellent! (1,000 reviews)

Jul 8 - Jul 12

4 night stay

Philadelphia (PHL) to Oakland (OAK)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,557, price is now $1,161 per person
$1,161
per person
found 1 day ago
Needs some upgrading to rooms and spa and charging for parking is something new and unpleasant now.

Reviewed on Jan 26, 2026

Solage, Auberge Collection
5.0-star property

Solage, Auberge Collection

9.6/10 Exceptional! (725 reviews)

Jul 8 - Jul 12

4 night stay

Philadelphia (PHL) to Oakland (OAK)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,927, price is now $2,127 per person
$2,127
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

Carneros Resort and Spa
5.0-star property

Carneros Resort and Spa

9.2/10 Wonderful! (367 reviews)

Jul 8 - Jul 12

4 night stay

Philadelphia (PHL) to Oakland (OAK)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,203, price is now $2,377 per person
$2,377
per person
found 1 day ago
The property was located in a very quiet area. It is very evident in some locations of the resort that service is extremely important. The Hilltop & Boonfly Café were consistently on top of service. The restaurant Farm lost points with us after a follow-up call was not received pertaining to reservation availability. The cottages themselves were very cute and had excellent amenities. The fireplace, fire pit, and outdoor tub/shower were so unique to our cottage experience. The cleanliness of the outdoor pillows, the curtains, and rugs were not pleasing. The outdoor rugs and cushions in the outdoor seating areas, particularly, near Farm were filled with pet hair & the floor rugs need to either be cleaned or replaced. The overall disappointing piece of the resort was the cleanliness. Even the hot tub had grime. With the amount of money paid to book the resort along with monies spent at the resort, there needs to be some revamping of the care.

Reviewed on Apr 3, 2021

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More About Flying To Windsor from Philadelphia

Route Information for Flights from Philadelphia to Windsor

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

Philadelphia 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.