Tag: family travel

  • We Flew In for Halloween Just to See the Steve Jobs House — Saved $91 Landing at OAK

    We Flew In for Halloween Just to See the Steve Jobs House — Saved $91 Landing at OAK

    This is exactly why a Bay Area Halloween house tour is worth flying in for. My friend Priya flew her family into Oakland instead of San Francisco this past Halloween week — $91 cheaper for the same October dates — just to drive her kids past a house that used to belong to Steve Jobs. 🎃✈️

    Most people have no idea the Bay Area even does this. Everyone knows Salem and New Orleans for Halloween. Almost nobody outside Silicon Valley knows that some of the most over-the-top, genuinely free Halloween decorations in the country are sitting in ordinary Peninsula neighborhoods, put up by the same families every single year.

    😩 The Problem: You’re Booking a Ticketed Haunted House When the Real Show Is Free

    Halloween Horror Nights tickets run $100+ per person before parking and food. A real Bay Area Halloween house tour costs exactly nothing beyond the flight and a tank of gas — you just need to know where to actually go, because none of this is on a map or a ticketing site. It’s neighborhood word-of-mouth, which is exactly why most visiting families miss it entirely.

    💡 The Discovery: Old Palo Alto, Menlo Park, and the Billionaire Halloween Arms Race

    Steve Jobs’ former home on Waverley Street in Old Palo Alto had a genuine, well-documented annual Halloween tradition — synthetic fog, rumbling thunder, jack-o’-lanterns, and gates that opened for trick-or-treaters every year, a tradition the family kept going even after his death. It’s been covered by AppleInsider, the Washington Post, and IEEE Spectrum, not just local gossip. The Washington Post has also written about the wider Peninsula phenomenon of wealthy tech families turning their yards into full productions every October — Old Palo Alto isn’t a one-house fluke, it’s a whole neighborhood culture.

    A few miles north, Menlo Park has its own current-day version: a family on Gilbert Drive built a full “Scare Wars” display last Halloween — a Star Wars-themed haunted yard, planned for years before they finally committed to building it. Local outlet InMenlo covers it annually, which is the easiest way to check what’s up that specific year before you fly in — these are real families doing this by hand, not a company, so displays do change year to year. If you want to widen the loop, Los Altos Hills runs a foggy “haunted forest” walk with lighting effects most seasons too.

    Landing at OAK instead of SFO put Priya’s family fifteen minutes closer to Menlo Park anyway, on top of the cheaper fare — see our full SFO vs OAK vs SJC breakdown if you’re deciding which Bay Area airport to fly into for this trip.

    🎉 The Reward: A Free Night That Beats Any Ticketed Attraction

    Priya’s kids went as an astronaut and a dinosaur, drove the loop with a thermos of cider, and were done by 9pm — no lines, no $100 ticket, no crowd control. The houses that go all-out do it because they genuinely want the neighborhood kids (and yes, visiting kids) to see it. That’s the whole appeal: real effort, zero admission fee, and a story your kids will actually remember over some rented fog machine at a mall haunted house.

    🚀 Action: Booking the Trip and Planning the Route

    Book the flight in on Kiwi.com first — compare OAK and SFO both, since OAK is frequently the cheaper option into the Peninsula and it’s the closer airport to both Old Palo Alto and Menlo Park. Cross-check with Aviasales, which regularly surfaces OAK fares that Kiwi doesn’t catch on its own. Aim to land by mid-afternoon on Halloween itself, or the weekend right before it — most of these displays run a few nights, not just the 31st.

    You’ll need a car to string the neighborhoods together — Old Palo Alto, Menlo Park, and Los Altos Hills aren’t walkable from each other. If you’d rather not rent and drive yourself around unfamiliar streets after dark with kids in the back seat, book a private pickup through GetTransfer instead — you tell the driver the three stops, they handle the route.

    • ✅ Fly into OAK, not SFO — usually cheaper and closer to the actual neighborhoods
    • ✅ Go early evening — most displays light up around dusk and wind down by 9-9:30pm on a school night
    • ✅ Check that year’s local coverage first — these are real families, not a company, so confirm a specific display is still running before you build a whole trip around one house

    ❓ Frequently Asked Questions

    Is the Steve Jobs house still decorated for Halloween every year?

    It’s been a documented tradition for well over a decade, but it’s a private family home, not a public attraction, so displays can change year to year. Check that year’s local coverage (InMenlo and similar Peninsula outlets post Halloween round-ups every October) before building a whole trip around one specific house.

    Do I need a rental car for this trip?

    Yes, or a booked transfer — Old Palo Alto, Menlo Park, and Los Altos Hills are each a short drive apart but not walkable from one another, especially with kids after dark.


    📍 See every West Coast Wings flight guide in one place: The Complete Guide to Cheap Flights from the Bay Area.


    Want your whole Bay Area Halloween trip planned, not just the flight? I build custom itineraries around your exact budget — DM @OlyaDreaMore or email hello@westcoastwings.org. See how custom planning works on the custom trip planning page.

    Subscribe to West Coast Wings for free weekly flight deals from SFO, OAK & SJC: westcoastwings.beehiiv.com · Join our Facebook group.


    Written by Olya | @OlyaDreaMore ✈️

  • Cheap Thanksgiving Flights from SFO, OAK & San Jose — Save $245+ (Book by Oct 15)

    Cheap Thanksgiving Flights from SFO, OAK & San Jose — Save $245+ (Book by Oct 15)

    Last November, I put off booking my Thanksgiving flight until the first week of October. By the time I looked, a nonstop SFO-to-Chicago flight that should’ve been $220 was quoting $465. I ended up flying through Denver with a 3-hour layover just to save $140. 😩 That’s the whole game with cheap Thanksgiving flights Bay Area travelers rely on — book early or pay the price. If you want the general booking-window logic behind this, check out our best time to book guide.

    Thanksgiving weekend (this year: Wednesday Nov 25 – Sunday Nov 29, 2026) is one of the single most expensive windows to fly out of the Bay Area all year — and almost nobody books early enough to avoid it.

    😩 The Problem: Why Cheap Thanksgiving Flights Bay Area Trips Get So Expensive

    SFO, OAK, and SJC all get slammed by the same crunch: everyone’s flying out Tuesday through Wednesday before Thanksgiving and flying back Sunday. Airlines know exactly how predictable that demand is, so fares climb steadily starting in October and spike hard in the two weeks before the holiday. Wait until “closer to the date” hoping for a deal, and you’re competing with the entire Bay Area for the same handful of seats.

    💡 The Discovery: Book by Mid-October, Fly Off-Peak

    Two things move the price way more than most people expect:

    • Book by October 15 — Bay Area Thanksgiving fares are historically at their lowest 5-6 weeks out. Past that, prices climb almost daily.
    • Fly Tuesday, not Wednesday — the Wednesday-before-Thanksgiving afternoon/evening block is consistently the single most expensive travel window of the entire year.
    • Come back Saturday instead of Sunday — the Sunday after Thanksgiving is consistently one of the most expensive return days on the U.S. flight calendar.
    • Check OAK and SJC alongside SFO — with everyone defaulting to SFO first, the smaller airports often still have real availability when SFO is already picked clean.

    Use Kiwi.com’s flexible date grid to see the whole week of prices at once instead of guessing — it makes the Tuesday/Saturday savings obvious immediately. Then cross-check the winning fare on Aviasales, since it pulls from different sources and sometimes catches a price Kiwi misses.

    🎉 The Reward: What Booking Early Actually Saves

    Shifting my flight to Tuesday and flying home Saturday instead of Sunday would’ve saved me that whole Denver detour — same nonstop route, $220 instead of $465. Book by mid-October and fly the off-peak days, and a round trip that normally runs $400-500 during Thanksgiving week often comes in closer to $200-250 instead.

    🚀 Action: Lock This In Before October 15

    Here’s exactly what to do this week:

    • 🔍 Open Kiwi.com and compare Tuesday/Wednesday departures against Saturday/Sunday returns side by side.
    • 🔁 Cross-check the fare on Aviasales before locking it in — Thanksgiving pricing moves fast once October starts.
    • 🛡️ Thanksgiving week means packed planes and a much higher chance of delays — if yours gets disrupted, AirHelp checks for compensation for free, and Compensair is worth a second look if AirHelp comes back empty.
    • 🚕 Landing late for the family dinner? Kiwitaxi locks in your airport transfer price ahead of time instead of paying holiday-surge rideshare rates.
    • 🧳 Early flight but the house isn’t ready for guests yet? Radical Storage holds your bags near the airport by the hour.
    • 🚗 Driving to see family once you land? EconomyBookings usually beats airport-counter rental prices, especially booked ahead of the holiday rush.

    ❓ Quick Questions

    What’s the actual cutoff to book cheap Thanksgiving flights from the Bay Area?

    Mid-October, roughly 5-6 weeks out. Prices are usually still reasonable through early October, then climb steadily as Thanksgiving week gets closer.

    Is OAK or SJC actually cheaper than SFO for Thanksgiving week?

    Often, yes — since most Bay Area flyers default to SFO first, OAK and SJC frequently still have seats (and lower fares) left after SFO’s cheapest fares are gone. Worth comparing all three before you book.

    Don’t wait until November hoping for a last-minute deal — Thanksgiving fares almost never drop that close to the holiday. Book by October 15, fly Tuesday out and Saturday back, and you’ll land at the family table for about half of what most people pay. 🦃✈️

    📍 See every West Coast Wings flight guide in one place: The Complete Guide to Cheap Flights from the Bay Area.


    Want your whole Thanksgiving trip planned, not just the flight? I build custom itineraries around your exact budget — DM @OlyaDreaMore or email hello@westcoastwings.org. See how custom planning works on the custom trip planning page.

    Subscribe to West Coast Wings for free weekly flight deals from SFO, OAK & SJC: westcoastwings.beehiiv.com · Join our Facebook group.


    Written by Olya | @OlyaDreaMore ✈️