Great winter destinations: How to get there with rewards

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Get some wintertime sun in San Diego, or relish the snowy mountains of Telluride

Lyn Mettler

Personal finance writer
Specializes in writing on travel, family and food


5 great winter destinations and how to get there with rewards

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As winter starts in Indiana, it’s not long before my family is itching to get out of the cold, dreary days for a getaway where we can enjoy snowy outdoor activities or bask in sunshine, even if just for a short time.

Here are five of our favorite wintertime destinations in the U.S., and some tips for getting there using rewards. 

San Diego 

One of our all-time favorite places in the U.S. is San Diego. Who can argue with average temperatures in the 70s year round? Plus, there’s so much to do, from plentiful beaches to adventure activities like hiking and kayaking, as well as museums, zoos and shopping.

San Diego can be a great locale to soak up some vitamin D in the midst of winter, no matter what you’re doing. Some of our top picks include kayaking in La Jolla, getting up close to sea lions and seals on the beaches, dining in the Little Italy neighborhood and visiting Sea World, which has fun rides in addition to its aquatic life.

We always fly to San Diego on Southwest Airlines, using points along with our Southwest Companion Pass that lets one person fly free with you (my husband, in our case). You can earn the Companion Pass more quickly by applying for a Southwest Rapid Rewards card to earn a hefty chunk of bonus points. There are also all sorts of major hotel brands in the city, allowing you to use hotel rewards for accommodations.

Telluride, Colorado

When it comes to mountain beauty, in my mind, Telluride simply can’t be matched. This Western gem of a town sits within a canyon surrounded by fantastic views of the jagged San Juan Mountains.

Telluride is known for its skiing in winter. You can hit the slopes in Mountain Village, which offers a free gondola into and out of the town. 

While there are a few flights directly into Telluride on United from Denver, most flights go into Montrose, which is about 65 miles away. You can take advantage of American Reduced Mileage Awards, which saves you up to 7,500 miles round trip based on holding select American credit cards like the Citi / AAdvantage Executive World Elite Mastercard on certain destinations (including Montrose during December and January). 

See related: Earn airlines miles through shopping portals this holiday season

Marco Island, Florida 

To get as warm as possible without leaving the U.S., consider a trip to Marco Island on the south Gulf Coast of Florida. Just south of Fort Myers and Naples, Marco Island sits just above the Everglades and is a quiet but lovely winter locale. We enjoyed 80-degree temperatures in late December one year!

We love to stay at the JW Marriott Marco Island, which you can book using Marriott Rewards points from the Marriott Rewards Premier Plus Credit Card, as it has multiple restaurants and several great pools. You can also hop on a jet ski right from the beach to zip through the Ten Thousand Islands for a tour and dolphin sightings. 

You’ll need to reach Marco Island via the Southwest Florida International Airport in Fort Myers – a nice, small airport that is one of my favorites. Delta, Southwest, American and United all fly into the airport.

Chicago

While the Windy City can get a touch bitter as the winter season arrives, to me it exudes a warm, cozy wintertime atmosphere, especially around the holidays. My happy memories might have something to do with getting engaged on the Chicago River as a light snow fell, but I truly adore Chicago during this season. It’s not crazy hot and muggy, a warm fire can blaze and you can take your pick of hot deep dish pizza to refuel any night of the week.

Lou Malnati’s and Gino’s East are great pizza spots. For a more gourmet meal, head to Harry Caray’s Italian Steakhouse in the River North District. The owner predicted the Cubs’ 2016 World Series win, and the restaurant contains lots of memorabilia of the legendary broadcaster it’s named for. 

We also recommend ice skating in Maggie Daley Park, catching a Chicago Bulls game or darting in and out of the plethora of shops on Michigan Avenue.

Chicago’s Midway Airport is a big hub for Southwest, often with cheap flights, and there is every hotel under the sun in town. We often like to stay in boutique accommodations like the multiple Kimptons, which you can book using IHG points from the IHG Rewards Club Premier Credit Card, as well as ACME Hotel Company Chicago, a trendy but fantastic, tech-friendly stay.

See related: 5 ways to maximize credit card rewards before year end

Palm Springs, California

While we have not made it to this hot spot in California as yet, it is on our bucket list, and I think this winter would be the perfect time to go. My husband loves mid-century modern architecture, which is overflowing in Palm Springs, and a desert oasis in the heart of cold wintry days sounds delightful to me. The area boasts highs of 71 to 74 degrees in January and February and is known for having more than 300 days of sunshine each year.

A trip to Joshua Tree National Park, a hike through Palm Canyon and an architecture tour would definitely be on the books, along with much sipping of tropical drinks by the pool. The bright and cheery Saguaro Palm Springs has long been a hotel I’d love to check out. American Airlines also has Palm Springs on its list of Reduced Mileage Awards for December and January, allowing you to use fewer miles to fly to the destination.

Where do you want to go this winter? 




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