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Travelling this winter? WalletHub names Chicago top holiday destination

  //travel-leisure.news-articles.net/content/2025/ .. ethub-names-chicago-top-holiday-destination.html
  Published in Travel and Leisure on Monday, November 3rd 2025 at 16:15 GMT by Journal Star

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Overview of the Ranking System

Wallethub’s methodology for ranking places is twofold. First, the article lists “cold” destinations that deliver quintessential winter experiences—think snowshoeing, ski resorts, and festive holiday markets. Second, it lists “warm” destinations where travelers can trade the cold for sunshine, gentle breezes, and tropical or desert adventures. For each category, the publication scored locations on three main criteria:

1. Winter Activities – Availability of ski slopes, holiday markets, winter festivals, or beach sunbathing.
2. Affordability – Average cost of accommodations, transportation, and activities, with a focus on value for money.
3. Holiday Atmosphere – The overall vibe of the destination during the holiday season, including decorations, local traditions, and crowd levels.

Each destination receives a composite score that reflects how well it performs across these criteria. The article also notes that the best choices change from year to year as hotels adjust prices and new resorts open, so the rankings are meant as a springboard for deeper research.

Cold‑Weather Destinations

Wallethub’s top cold‑weather picks offer classic winter charm and a range of activities for families, couples, and solo adventurers alike. The top three places mentioned are:

1. Aspen, Colorado – Known for its world‑class ski slopes and upscale après‑ski scene, Aspen tops the list for those seeking a high‑end winter escape. The article highlights the “Aspen Snowmass” complex, which provides access to four distinct ski areas in one ticket. A highlight is the “Christmas in Aspen” festival, featuring carolers, lights, and a traditional New Year’s Eve fireworks show. Prices are steep, but the value comes from the quality of the slopes, the resort amenities, and the guaranteed snow conditions.

2. Banff, Alberta – Canada’s “gateway to the Rockies” offers an affordable yet pristine winter experience. The article notes that Banff’s ski resorts (Lake Louise, Sunshine Village, and Mt. Norquay) have lower lift ticket prices compared to Aspen, and the town itself has a charming holiday market in the central plaza. The “Banff Winter Carnival” is also mentioned, a celebration that includes ice sculpting contests, sleigh rides, and local craft vendors.

3. St. Moritz, Switzerland – The legendary Swiss resort receives a high score for its luxury appeal and historic “Olympic” status. The article points out the “St. Moritz Christmas Market” that dates back to the 19th century, and the opportunity for winter sports enthusiasts to combine skiing with world‑class spa experiences. While the prices are the highest on the list, the resort’s reputation for winter elegance is unmistakable.

Other notable cold destinations include:

• Lake Tahoe, California/Nevada – The article highlights the “Christmas in Tahoe” festivities and the affordability of its ski resorts.
• Jackson Hole, Wyoming – Known for its rugged scenery and vibrant “Wildlife Fest,” the article notes the town’s holiday lights and the close proximity of Grand Teton National Park for wildlife spotting.
• Rovaniemi, Finland – The official hometown of Santa Claus, Rovaniemi receives praise for its family‑friendly holiday activities, such as visiting Santa’s village and viewing the Northern Lights.

Warm‑Weather Destinations

For travelers who prefer to trade snow for sand, Wallethub’s warm‑weather section focuses on places that combine affordable travel with plentiful holiday activities.

1. Maui, Hawaii – Maui tops the warm list, thanks to its iconic beaches, the “Maui Holiday Market” in Lahaina, and the “Maui New Year’s Eve Celebration” featuring a fireworks display at the beach. The article points out that while flights to Hawaii can be pricey, accommodation rates tend to be reasonable during the off‑peak winter season (late November to mid‑January).

2. San Diego, California – The article recommends San Diego for its mild weather and “San Diego Christmas Parade.” Visitors can enjoy holiday lights at Balboa Park and the historic “Mission Beach Christmas Lights” display. The city’s extensive array of family-friendly attractions—such as the San Diego Zoo and Legoland—makes it a versatile choice.

3. Palm Springs, California – Known for its desert heat, Palm Springs is highlighted for its “Palm Springs Holiday Lights” at the Living Desert Zoo and the “Winterfest” events in the downtown area. The article notes that the desert scenery provides a unique backdrop for holiday festivities, and the region’s resorts offer great value for travelers seeking sun and relaxation.

Other warm destinations mentioned include:

• Mexico City, Mexico – The city’s historic “Noche de los Rabanos” (Rabbit Night) and holiday markets make it a culturally rich option.
• Miami, Florida – With its “Miami Holiday Parade” and festive decorations along Ocean Drive, Miami is praised for its blend of beach culture and holiday celebrations.
• New Orleans, Louisiana – The article highlights the city’s “New Orleans Holiday Market” and the festive “Christmas in the French Quarter” events.

Practical Travel Tips

Across both cold and warm categories, the article provides actionable advice to help travelers make the most of their winter trips:

• Book Early, but Stay Flexible – The article suggests booking flights and accommodations at least six to eight weeks in advance. It also recommends keeping an eye on price drops in the last month, especially for destinations that open or close hotels during the holidays.
• Consider Package Deals – Wallethub notes that many resorts offer “holiday packages” that bundle lodging, lift tickets, and meals. These can provide significant savings for groups and families.
• Travel Insurance is a Must – For winter destinations, the article stresses the importance of insurance that covers weather‑related cancellations or medical emergencies.
• Pack Appropriately – The article reminds readers to bring the right layers for cold destinations, and suggests waterproof jackets for destinations that can receive sudden showers (e.g., coastal California).
• Explore Local Festivities – In both categories, the article recommends visiting local markets, attending holiday concerts, and participating in regional traditions to fully experience the destination’s holiday spirit.

Additional Resources and Links

Wallethub’s article includes links to deeper dives on each destination’s travel page. These links typically direct readers to official tourism sites, where travelers can find up‑to‑date information on events, accommodations, and transportation. The article also provides sidebars with “Quick Facts” about each destination, such as average temperatures, best time to visit, and travel restrictions.

Conclusion

Whether you’re chasing powder at Aspen, exploring the snowy markets of Rovaniemi, or soaking up sun on Maui’s shores, Wallethub’s ranking provides a clear snapshot of the most appealing winter destinations for both cold‑and‑warm‑weather lovers. By combining a structured scoring system with practical advice and local highlights, the publication equips readers with the knowledge they need to choose a holiday destination that fits their budget, interests, and desired seasonal atmosphere. The article’s emphasis on early booking, travel insurance, and exploring local traditions ensures that travelers can enjoy a memorable, stress‑free winter getaway.