Cheap flights To Wine Country (OAK) from $46

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Cheap Flights to Wine Country from $46 One Way, $104 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jun 9 - Wed, Jun 10
SAN
San Diego Intl.
OAK
Oakland Intl.
$104 Roundtrip, found 6 days ago
$104
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Jun 9 from San Diego Intl. to Oakland Intl., returning Wed, Jun 10, priced at $104 found 6 days ago
Tue, Jun 9 - Wed, Jun 10
SAN
San Diego Intl.
OAK
Oakland Intl.
$114 Roundtrip, found 6 days ago
$114
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jun 9 from San Diego Intl. to Oakland Intl., returning Wed, Jun 10, priced at $114 found 6 days ago
Wed, May 13 - Sat, May 16
ONT
Los Angeles - Ontario Intl.
STS
Sonoma County
$117 Roundtrip, found 10 hours ago
$117
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Wed, May 13 from Los Angeles - Ontario Intl. to Sonoma County, returning Sat, May 16, priced at $117 found 10 hours ago
Wed, Jun 24 - Tue, Jun 30
SAN
San Diego Intl.
OAK
Oakland Intl.
$117 Roundtrip, found 7 hours ago
$117
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Wed, Jun 24 from San Diego Intl. to Oakland Intl., returning Tue, Jun 30, priced at $117 found 7 hours ago
Wed, May 6 - Sat, May 9
SAN
San Diego Intl.
OAK
Oakland Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, May 6 from San Diego Intl. to Oakland Intl., returning Sat, May 9, priced at $119 found 1 day ago
Tue, May 12 - Wed, May 20
BUR
Hollywood Burbank
STS
Sonoma County
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, May 12 from Hollywood Burbank to Sonoma County, returning Wed, May 20, priced at $140 found 5 days ago
Sat, May 23 - Tue, May 26
LAX
Los Angeles Intl.
STS
Sonoma County
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, May 23 from Los Angeles Intl. to Sonoma County, returning Tue, May 26, priced at $140 found 6 days ago
Tue, May 5 - Tue, May 12
SAN
San Diego Intl.
STS
Sonoma County
$147 Roundtrip, found 20 hours ago
$147
Roundtrip
found 20 hours ago
Select Alaska Airlines flight, departing Tue, May 5 from San Diego Intl. to Sonoma County, returning Tue, May 12, priced at $147 found 20 hours ago
Wed, Jun 3 - Tue, Jun 9
PHX
Sky Harbor Intl.
OAK
Oakland Intl.
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Wed, Jun 3 from Sky Harbor Intl. to Oakland Intl., returning Tue, Jun 9, priced at $171 found 6 days ago
Tue, Jun 9 - Wed, Jun 10
SAN
San Diego Intl.
OAK
Oakland Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 9 from San Diego Intl. to Oakland Intl., returning Wed, Jun 10, priced at $177 found 6 days ago

Wine Country Flight Information

Traveling To
Wine Country
Destination Airport IATA Code
OAK
Number of Airlines Serving
Airlines
Southwest Airlines, Alaska Airlines, Delta
Flight Price
$104
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Wine Country economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyland Motel Van Nuys
2.5-star property

Hyland Motel Van Nuys

May 29 - Jun 1

3 night stay

Dallas (DFW) to Los Angeles (LAX)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $723, price is now $401 per person
$401
per person
found 1 day ago
Kona Kai San Diego
4.0-star property

Kona Kai San Diego

May 13 - May 19

6 night stay

Dallas (DAL) to San Diego (SAN)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,926, price is now $1,137 per person
$1,137
per person
found 1 day ago
AKA Beverly Hills
4.0-star property

AKA Beverly Hills

May 27 - Jun 3

7 night stay

Dallas (DFW) to Los Angeles (LAX)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,654, price is now $2,206 per person
$2,206
per person
found 23 hours ago
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Wine Country premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Beacon Grand, A Union Square Hotel
4.0-star property

Beacon Grand, A Union Square Hotel

9.2/10 Wonderful! (1,948 reviews)

May 30 - Jun 1

2 night stay

Chicago (ORD) to San Francisco (SFO)

United • Roundtrip • PremiumEconomy
Price was $1,097, price is now $955 per person
$955
per person
found 1 day ago
Great experience and two free welcome drinks.

Reviewed on Jan 3, 2026

Hotel Riu Plaza Fisherman's Wharf
4.0-star property

Hotel Riu Plaza Fisherman's Wharf

9/10 Wonderful! (7,351 reviews)

May 30 - Jun 1

2 night stay

Chicago (ORD) to San Francisco (SFO)

United • Roundtrip • PremiumEconomy
Price was $1,116, price is now $975 per person
$975
per person
found 1 day ago
perfect location amazing hotel and the best hotel breakfast i have ever seen

Reviewed on Feb 13, 2026

The Ritz-Carlton, San Francisco
5.0-star property

The Ritz-Carlton, San Francisco

9.4/10 Exceptional! (1,002 reviews)

May 30 - Jun 1

2 night stay

Chicago (ORD) to San Francisco (SFO)

United • Roundtrip • PremiumEconomy
Price was $1,329, price is now $1,176 per person
$1,176
per person
found 1 day ago
Absolutely love staying here! Club level is wonderful, staff is top notch!

Reviewed on Aug 13, 2025

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See all available trips from Chicago to Wine Country
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Wine Country first class flight packages

Price found within the past 48 hours. Click for updated prices.
The LEEF Hotel
2.0-star property

The LEEF Hotel

8.6/10 Excellent! (570 reviews)

May 25 - Jun 1

7 night stay

Seattle (SEA) to Los Angeles (LAX)

American Airlines • Roundtrip • FirstClass
Price was $1,245, price is now $790 per person
$790
per person
found 1 day ago
Clean room and comfortable

Reviewed on Mar 23, 2026

Hotel Angeleno
4.0-star property

Hotel Angeleno

8.6/10 Excellent! (2,121 reviews)

May 25 - Jun 1

7 night stay

Seattle (SEA) to Los Angeles (LAX)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,877, price is now $1,171 per person
$1,171
per person
found 1 day ago
I didn’t like that I had to wait 2 hours in the lobby after I checked in

Reviewed on Oct 27, 2025

Pendry Newport Beach
4.5-star property

Pendry Newport Beach

9.4/10 Exceptional! (529 reviews)

May 25 - Jun 1

7 night stay

Seattle (SEA) to Orange County (SNA)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,131, price is now $1,473 per person
$1,473
per person
found 1 day ago
We loved staying at the Pendry this past March of 2024. Our room was spacious, very well appointed, quiet, and luxurious. No expsnes or amenities were spared in any way! The gym was top notch, hi tech and fully loaded with everything you'd pexpect, plus more. The staff was incredibly attentive and professional- Emily stood out to us at breakfast time at Bar Pendry. We look forward to staying at the Pendry once again in two month's time.

Reviewed on Mar 5, 2024

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Wine Country

If you are looking for affordable flights to Wine Country, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Wine Country now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Wine Country flights. With Orbitz, booking flights to Wine Country is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Wine Country flights by visiting the Orbitz site or mobile application.

Orbitz looks after you

Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Wine Country flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Wine Country flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

Frequently asked questions

Which airlines fly to Wine Country?
You're spoiled for choice with 20 major airlines that jet into San Luis Obispo County Regional Airport (SBP). Compare airfares and score yourself an affordable flight to Wine Country with any one of these leading carriers:

  • United Airlines - 121 flights to Wine Country per month
  • Alaska Airlines - 45 flights to Wine Country per month
  • American Airlines - 40 flights to Wine Country per month

What is the best airport to fly to in Wine Country?
Touch down at San Luis Obispo County Regional Airport (SBP), the primary gateway to Wine Country. Organizing your flight to this region doesn't get much easier than that.
How much is a flight to Wine Country?
Travelers from near and far picked up round-trip bargains ranging between $104 and $177 this week. Starting your journey from San Diego (SAN)? The best one-way prices were just $46.
How to book the cheapest flight to Wine Country?
With some of the most amazing flight deals around, you'll always get more for your money with Orbitz. The following suggestions will help you pick up cheap flights to Wine Country — and leave you with more money in your pocket:

  • Depending on your departure city, click on the 'Nearby airports' function (located under the departure and arrival form fields). Sometimes, alternative departure points offer better value for money.
  • If your plans aren't set in stone, click on the 'Show flexible dates' link to view the flight deals for alternative departure dates. Go with any suitable cheaper fare you find.
  • Select 'Show options' to filter your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • If you've worked out your travel dates, don't drag your feet booking a flight. Airfares normally become more expensive as the departure date nears.
  • Consider combining your hotels, flights and car rentals with Orbitz to make your dollar go further.
  • If practical, avoid traveling in the most popular seasons. Airfares significantly increase during school breaks, summer and around other vacation times like Easter, Thanksgiving and Christmas.

How long is a flight to Wine Country?
Flight times differ based on where you're leaving from. But to give you a good idea of the average duration, take a peek at these top routes to Wine Country:

  • San Francisco, CA (SFO-San Francisco Intl.) to San Luis Obispo County Regional Airport (SBP) - 1 hour and 7 minutes
  • Denver, CO (DEN-Denver Intl.) to San Luis Obispo County Regional Airport (SBP) - 2 hours and 51 minutes
  • Phoenix, AZ (PHX-Sky Harbor Intl.) to San Luis Obispo County Regional Airport (SBP) - 1 hour and 44 minutes

What is the best time to book a flight to Wine Country?
Purchase your tickets to Wine Country in January. This is the perfect time of the year for bargain airfares, followed by February and August. Pick up cheap flights and enjoy your dream getaway with Orbitz.
What day of the week is the cheapest to book a flight to Wine Country?
If you're after cheap airfares to Wine Country, the best days to make a booking are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), a superb flight deal will be all yours.
What is the cheapest day of the week to fly to Wine Country?
Everyone enjoys saving money, so think about departing earlier in the week for cheap flights to Wine Country. Orbitz data from 2020 suggests you can grab the best prices on flights that take off on Mondays. Tuesdays are the next most affordable day, while Saturdays are the costliest. Many passengers like to travel at the weekend, so leave those Saturdays for checking in with friends.
What is the cheapest month to fly to Wine Country?
Fly during August if you don't want to put a dent in your budget. Orbitz data has found that it's generally the best month for cheap flights to Wine Country. June is when ticket prices are at their highest.
Which airlines allow free cancellation?
If you think your travel plans may change, Orbitz will help you find a flexible fare. All you need to do is choose "Filter by flexible change policies" when searching for your perfect flight. We'll show you airlines that offer free cancellation and no change fees — along with our famous low prices.
What do I need for the flight to Wine Country?
There's so much to sort out for any big trip, so it's great to get some help before you set out. Here are a few tips to ensure that you're prepared for your flight:

  • Ensure that you have your travel documents and identification. For international trips, you'll need to bring your passport. When purchasing your tickets, always use the same name, birth date and gender as indicated on your current ID.
  • A well-packed carry-on bag is a must for any medium-haul flight. With at least a few hours up your sleeve, you'll need something to keep you entertained while in the air. We suggest a good book or magazine, and something to nibble on.
  • Aircraft cabins can get chilly. Even if you're traveling during the height of the Wine Country summer, make sure you take an extra warm layer with you.

How many direct flights are there to Wine Country?
Carriers such as United Airlines, American Airlines and Alaska Airlines operate 36 direct services to Wine Country every month. With loads of options at your fingertips, booking your ideal nonstop flight will be a breeze.
How do I get cheap first-class/business deals to Wine Country?
There are ways of booking first or business-class airfares to Wine Country that won't burn a hole through your budget. Bag a seat in the pointy end of the plane for less with these helpful tips:

  • Flexibility is important. By being open to a few travel dates, you'll have more chances of finding a deal on your airfares.
  • Many low-cost carriers these days have terrific business-class seating without the hefty fees.
  • Make a bid for an upgrade. Some airlines hold online auctions that let you put down a price for a seat at the front of the plane. You can also try upgrading with points earned through a loyalty program.

More to Explore

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.