4 Awesome Destinations for a Winter Weekend Getaway
Quick trips, big adventures
It’s a fresh year, and you guys know what that means: time to start planning your 2026 adventures! And you don’t have to wait for spring break or summer. A winter weekend getaway is just as exciting. A quick escape over a chilly weekend is the perfect way to kick off the year—and shake off those back-to-work blues.
These destinations are perfect for starting your year with a little spontaneity and a lot of fun!
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Chicago, IL
Big city energy + a touch of winter magic!
Well, more than a touch. Chicago is cold in the winter, you guys! But it’s nothing that your warmest boots can’t handle. And we promise, it’s worth it. The Windy City leans into the season, with something for everyone. Culture lovers can explore world-class museums and watch a Broadway-caliber show. Foodies will enjoy everything from a deep-dish pizza to innovative steak offerings at trendy chophouses. And sports fans can cheer for their favorite NBA or NHL team.
If the weather (and your winter accessories!) cooperate, bundle up for a walk along the lakefront. The city’s iconic skyline feels extra dramatic with a snowy backdrop. Afterwards, warm up in a cozy cocktail lounge with some live jazz music.
Best Winter Weekend Getaway: for city explorers
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Monterey, CA
Cool coastal charm!
While SoCal is all about that bright and sunny lifestyle, Monterey has a completely different vibe. Think dark, moody, and slightly dramatic. And winter is one of the best times of year to experience its beauty! One of the area’s standout features is the Monterey Bay Coastal Recreation Trail. Bike or walk along its 18 paved miles for scenic views, fresh air, and easy access to the area’s main attractions.
On the trail and off, winter is primetime for wildlife watching in Monterey. Migrating gray whales are surprisingly close to shore. You’ll see them, plus dolphins and sea otters, from the shoreline or on guided tours. And if you want to learn more about them, the Monterey Bay Aquarium and its interactive exhibits are a must!
Best Winter Weekend Getaway: for nature lovers
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Orlando, FL
Fantastic weather, fewer crowds!
Falling perfectly between the holidays and spring break, mid-winter is possibly one of the absolute best times to visit Central Florida. With fewer people at theme parks, wait times are shorter, and discounts on hotels and dining are easier to find. It’s as relaxed as a theme park visit can be!
Orlando is also just a short drive from Florida’s Space Coast. Rent a wetsuit and a surfboard, and hit the waves on a sunny afternoon. Take an airboat ride through the wetlands. Or explore the rocket garden, museums, and hands-on exhibits at Kennedy Space Center. If you time it just right, you may even catch a rocket launch IRL.
Best Winter Weekend Getaway: for traveling with kids and kids at heart
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Santa Fe, NM
Where cold and culture come together!
Winter in Santa Fe is undeniably cold—but beautifully so. With sunny skies and dry weather, you can bundle up and stroll through the heart of the city. Browse Native American jewelry, art, and artisanal goods sold directly by the artists themselves at the historic Santa Fe Plaza. Visit museums celebrating everything from the area’s Indigenous heritage to contemporary design.
Cold afternoons are perfect for gallery hopping along Canyon Road. Local and international artists alike are featured in dozens of art spaces. Need to warm up? Get a real “taste” of Santa Fe by diving into its food scene, with its bold use of red and green chile. There’s no tastier way to bring the heat!
Best Winter Weekend Getaway: for chilly + chile
A winter weekend in one of these cities is sure to create memories that keep you smiling all year long!
And to make sure your travels bring a smile to your face, too, ship your stuff to your hotel or Airbnb with LugLess. No hauling heavy bags full of winter gear through the airport, no wasting precious weekend time at baggage claim. So you can enjoy every minute of your weekend escape!