4 Fantastic Winter Travel Destinations for Families to Visit on Southwest

Signing up for credit cards through partner links earns us a commission. Terms apply to the offers listed on this page. Here’s our full advertising policy: How we make money.

Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers.

Lyn writes about how to fly free on Southwest on her GotoTravelGal.com blog.  And wrote a free guide on how to earn the coveted Southwest Companion Pass that lets 1 person fly nearly free with you for up to 2 years.  I’ve asked her to share some fun winter travel destinations for families and how you can get there on Southwest.

Lyn:   We largely fly free around the US and are amazed at how many great – and varied – places there are to visit in our country.  We love to fly Southwest, because we can each check 2 bags, there are no change or cancellation fees, and we can book any flight any time so long as we have the points.  

There are NO blackout dates on Southwest.  As long as a seat is for sale, you can use points to book it!

Whether you’re looking for a warm getaway this winter, or in search of snow, here are some of our favorite options.  You can reach them by flying directly to the city on Southwest, or to a city within an hour or so of the destination.

1.   San Diego

Link:   Use Southwest Points to Save Money on a Family Trip to San Diego

San Diego is one of my family’s favorite US cities to visit.  The weather is perfect (averaging the mid-70s year round), there are lots of beaches, and tons of family-friendly outdoor activities.  We even headed to the city this summer to experience Comic Con for the first time!

Here are some of our top recommendations for things to do in San Diego:

• Wander through the hip Gaslamp Quarter downtown, exploring the amazing outdoor Horton Plaza Mall
• Visit during October when kids get in free to many top attractions
• Eat dinner in downtown’s Little Italy neighborhood
• Get close to sea lions on the rocky cliffs in La Jolla
• Start at The Cave Store and walk down into a sea cave (also in La Jolla)
• Visit the San Diego Zoo
• Meander through Balboa Park, the nation’s largest urban cultural park
• Spend a day at SeaWorld San Diego
• Take a spin on the rides at Belmont Park in Mission Beach
• Rent bikes and explore Coronado Island
• Hike Torrey Pines State Reserve for gorgeous coastal views
• Tour the U.S.S. Midway aircraft carrier

2.   Colorado Springs

If you love the outdoors – and gorgeous scenery – Colorado Springs is fantastic option for families.  With more than 300 days of sun each year, even a cool winter day seems perfect with snow blanketing the Rocky Mountains, Pikes Peak, and the lovely landscape.

To visit Colorado Springs on Southwest, you’ll need to fly to Denver, and drive south (or take a shuttle) to Colorado Springs – about 70 miles.

If you want to ski, there are resorts within a couple hours, but its mild winter temperatures averaging from the low 30s to upper 40s make it a great climate to get outdoors and enjoy the scenery all year.

Here are some of our favorite things to do in Colorado Springs:

• Take the historic Cog Railway to the top of Pikes Peak and enjoy homemade donuts at the top!
• Hike the free Garden of the Gods park where massive ancient red rocks jut out of the earth
• Visit Cheyenne Mountain Zoo, America’s only mountain zoo
• Walk through an 1800s Wild West ghost town at the Ghost Town Museum
• Hike to the top of Broadmoor Seven Falls, a series of 7 waterfalls
• Tour the Olympic Training Center where Olympic athletes come to train
• Walk through a 500-million year old cave at Cave of the Winds
• See real dinosaur fossils at the Royal Gorge Dinosaur Experience
• Ride the Cripple Creek & Victor Narrow Gauge Railroad
• Walk through cliff-side caves where ancient people made their home at the Manitou Cliff Dwellings

3.   Myrtle Beach

While Southwest does not fly directly into Myrtle Beach, they do fly to Charleston, which is only 95 miles south and also a great city!  We used to live in Charleston and would drive to Myrtle Beach for the day often, because there are so many attractions.

Also with a mild winter climate and many days of Carolina sunshine (with even a few days in the 70s!), Myrtle Beach offers miles of beaches and tons of activities to keep everyone entertained.

Some fun things to do in Myrtle Beach:

• Play at your hotel!  Most Myrtle Beach hotels have indoor waterparks, lazy rivers, multiple pools, jacuzzis, and more – perfect for cooler winter days
• Walk the beach.  Bring a metal detector to look for lost jewelry and coins or search for shells
• Visit Broadway at the Beach, a large entertainment district with shopping, dining, and lots of attractions
• Pet stingrays at Ripley’s Aquarium
• Get a fun lesson in science at WonderWorks, which you will know because it “looks” like an upside down house from the outside
• Ride the Myrtle Beach SkyWheel, which is the highest observation point of the Atlantic in North America
• Play a round of mini golf, which are a dime a dozen in Myrtle Beach with every theme under the sun
• Walk the boardwalk.  You’ll love the people-watching, dozens of arcades, and ocean views
• Find a bargain.  The Grand Strand has several top outlet malls including Tanger Outlets with more than 200 brands

4.   Beaver Creek

My family has owned a condo in Beaver Creek since the 1980s.  And it’s one of our favorite places to visit both winter and summer.  You’ll need to fly into Denver to reach Beaver Creek Resort, which is about 100 miles west.  And then rent a car or hop on the Colorado Mountain Express, which takes you to the village.

Beaver Creek is very close to Vail, but much quieter.  You’ll find shorter lines and less crowded terrain.

Here are some of our favorite things to do in Beaver Creek, Colorado:

• Ski, ski, and ski some more.  Take kids to the new Red Buffalo Park ski area, which offers fun features like snow sculptures and fun things to ski through
• Take a sleigh ride to dinner in the mountains at Allie’s Cabin
• Go snowmobiling and look for wildlife like elk and deer
• Enjoy fresh chocolate chip cookies on the mountain and in the village daily – free
• See a show at the Vilar Performing Arts Center
• Go ice skating at the rink in Beaver Creek Village
• Enjoy pizza at Blue Moose Pizza
• Grab a yummy gelato at Rimini in the village
• Snuggle by the fire in your hotel or condo, and play a board game while the snow falls out your window
• Enjoy an Italian dinner at Toscanini while the kids play on Etch-a-Sketches before your meal

Remember, even if Southwest does not fly directly out of your home airport, they may fly out of an airport nearby.  For example, although Southwest flies out of Indianapolis, our home airport, we sometimes drive ~2.5 hours north to Chicago-Midway to take advantage of lower fares.  Here’s Southwest’s route map to check where they fly!

Collecting Southwest Points for Your Trip

Link:   Southwest Rapid Rewards® Plus Credit Card

Link:   Southwest Rapid Rewards® Premier Credit Card

Link:  Southwest Rapid Rewards® Premier Business Credit Card

The quickest way to collect Southwest points for your flight is to sign-up for 1 or more of the Chase Southwest cards, both personal and business, and earn the sign-up bonus.

Or, you can sign-up for a credit card that earns Chase Ultimate Rewards points, including the Chase Sapphire Preferred® Card, Ink Business Preferred℠ Credit Card, and Chase Sapphire Reserve, and earn the sign-up bonus after meeting the minimum spending requirements.  These points, which you can continue to earn through spending on the card, also transfer instantly to Southwest at a 1:1 ratio.

Bottom Line

Southwest has wonderful destinations you can reach this winter with plenty of family-friendly activities.  Choose from beaches or snow-covered mountains to visit:

• San Diego
• Colorado Springs
• Myrtle Beach
• Beaver Creek

Put your Southwest points to use for a family award trip with NO blackout dates.  And don’t forget you can transfer Chase Ultimate Rewards points to Southwest, too!