So this is not one I have ever seen before. Southwest has single stop flights to Portland (during ski season) for $122 Round-Trip — Ski Bags included! To give you an idea of how insane that is I would normally consider $250 round-trip a 'Good Deal' (since flights to PDX have been averaging $350-400) — this is less than half of that.

Hood River Vacation Rentals also has 2-3 bedroom options (sleeps 6-8) for $120-$160/nt PLUS stacking coupon code: 602U for $60 OFF 3+ night stays AND 30% off lift tickets ($30/day).

40% off Longboard Skateboard w/Trip — to sweeten the pot further the guys at Original Skateboards (longboards, downhill decks etc) decided to kick in a 40% Discount off any Complete Board for anyone who makes the trip. That should save $150+ — basically it pays for your flight — and gets a Christmas present out of the way while you are at it! (details below). Plus you get to have a skate with the guys in Portland while you are at it.

Newark to Portland is almost always $375+ — these cheap ski trips save 65% and get you there with One-Stop on Southwest.

Per usual the free checked Ski Bags on Southwest should save you about $140 Round-Trip. If you were to factor that in these ski trip flights are an astounding 80% off what you would pay on jetBlue, Delta, United etc.

Hard to beat skiing my favorite volcano for less than $200. For anyone who doesn't realize the quality terrain Hood has to offer — here's a another look at some riding Decembers past (here is last year):

Original Skateboards 40% Off X-Mas Present Promo

So as mentioned up top I called up the guys at Original Skateboards (which I co-founded in 2002!) who just recently moved out to PDX to see if they wanted to collaborate on a deal for anyone who makes the trip out to Portland on Southwest (November 30th - December 12th).

We all agreed that Portland is worth seeing, worth skiing, and 100% worth skating — and Will and the guys offered to hook up a seriously mind blowing 40% discount on any Complete Board — for anyone who makes the trip (and shows them an official Printed / Paper Boarding pass Newark - Portland on Southwest).

If you end up going and want to order AFTER you need to make sure you get the legit airline boarding pass from the gate (not the print at home one!)

Just a suggestion but I HIGHLY recommend the Apex 40 DiamondDrop (designed this one!) — here's a video of me introducing it back in the day:

Cheap Lodging + Lift Tickets

Best option that I found thus far on lodging is with Hood River Vacation Rentals. Booking with them via their Deals Page gets you a 2-3 bedroom place (plenty for 6-8 people) a short drive to the resort for $120-$160/nt PLUS stacking coupon code: 602U for $60 OFF 3+ night stays.

You can pair that with a 4 of 6 day pass at Hood Meadows (30% off) for $129 bucks total (works out to $30 a day).

How to Book Southwest

Since southwest doesn't allow direct links to specific dates, the best way to go about this is to hit the Southwest Low Fare Calendar. From there enter the airport you want to fly from (EWR to PDX) and then select December (alternately November):

That should land you on the right calendar. You are looking for the flights that are $62 on the way out there, and $62 on the way back. Generally the sale covers November 30th through December 12th with some fantastic long weekend options (although you should probably just stay longer!)

Once you select a date you want to hit continue at which point you are looking for the Non-Stop 'Wanna Get Away' flights (which for some reason are generally cheaper than those with more stops).

Southwest Free Change Fees

One of the best parts about Southwest is that they cover free change fees. That is freaking KEY when you may want to push your reservation around to avoid an incomming NY/NJ side storm (or if you find a cheaper price later — not possible in this case hah).

This has saved more times than I can count. The Free Ski Bags things helps too.

In Closing (One More Push over the Edge)

Just in case you need one more push over the edge — the guys at OnTheSnow make a pretty solid argument on why you should check it Mt. Hood. I found WAY too many videos epic mt. hood riding but really enjoyed this one: