Celebrate the Holiday Season in One of These Festive Spots

From Thanksgiving through the new year, you’ll discover that Nantucket, Chicago, New Orleans and Breckenridge are brimming with holiday cheer.

by NEA Member Benefits

Nantucket, Massachusetts

Winter is the quiet season on Nantucket, when islanders revel in sweet, time-honored traditions. The holiday fun begins with a jolt on Thanksgiving morning, with the Cold Turkey Plunge into the bracing waters of the Atlantic at Children’s Beach.

Holiday decorations reflect this New England island’s maritime heritage. A large wreath graces the Brandt Point Lighthouse, trees sprout from the bows of boats, and strings of lights illuminate sailboat masts. The Nantucket Historical Association Whaling Museum displays dozens of decorated evergreens at its Festival of Trees.

Nantucket’s holiday highlight is the annual Christmas Stroll weekend (taking place December 1 - December 3 in 2023). It seems everyone on the island wanders the downtown cobblestone streets, which are filled with decorated storefronts and Victorian carolers. A town crier announces the arrival of Santa Claus—by Coast Guard cutter!

NEA member travel benefits: You’ll want to book airfare tickets into Nantucket Memorial Airport (ACK), and you can find deals on flights there through NEA Travel: Flights. Click on the hotels page to see off-season prices like an average of $182/per night at the Nantucket Inn, a charming boutique hotel with free breakfast and indoor pool and hot tub. The historic Jared Coffin House is an average of $201/per night and offers quaint rooms and complimentary breakfast.

Plan your itinerary: Nantucket Chamber of Commerce | Massachusetts Office of Travel & Tourism 

Chicago, Illinois

The Second City is second to none when it comes to holiday revelry. On Thanksgiving morning, thousands of spectators line State Street for the McDonald’s Thanksgiving Day Parade. Large inflatable balloon characters, decorated floats and marching bands highlight the event, an annual tradition since the Great Depression.


Downtown’s Daley Plaza hosts Christkindlmarket, the largest open-air German Christmas market outside Europe. It features market stalls selling holiday ornaments, toys, food and other gifts, along with live entertainment by choirs and bands. The Magnificent Mile Lights Festival kicks off the holiday season with a festive lights display and parade that brightens one of the city’s key shopping districts along Michigan Avenue.

Along the Lake Michigan waterfront, Navy Pier celebrates the season at Light Up the Lake, an enormous indoor winter playground with more than 600,000 twinkling lights across dozens of holiday-themed sculptures. It’s a heady mix of holiday decorations and kid-pleasing attractions, including a skating rink, a birch tree forest maze, a holiday train ride in Santa’s Village and visits with the jolly man himself.

NEA member travel benefits: Fly into Chicago O’Hare International Airport (ORD) or Chicago Midway International Airport (MDW) by searching for airline tickets through NEA Travel: Flights. Next, search for hotel deals like rooms at the historic and design-focused Chicago Athletic Association, the Unbound Collection by Hyatt, right by Millennium Park, for an average of $149 a night. For $98 a night on average you can stay at Hilton Garden Inn Chicago Downtown Riverwalk, close to Navy Pier. The Westin Michigan Avenue is a steal at an average of $150 a night in winter, with spacious, comfortable rooms and a 24-hour gym.

Plan your itinerary: Choose Chicago | Enjoy Illinois

New Orleans, Louisiana

No city knows more about celebrating than the Big Easy. In November and December, visitors enjoy a busy roster of holiday events along with mild weather and some of the best hotel rates of the year. On Thanksgiving, you’ll find special dinner menus at many restaurants. Here’s your chance to try that Cajun specialty, a turducken: a turkey stuffed with a duck stuffed with a chicken.

More than 1 million lights illuminate the moss-draped cypress and live oaks in City Park during the holidays. Celebration in the Oaks activities include a 2-mile train ride through the lights and the animated “The Cajun Night Before Christmas” display.

Holiday decorations also festoon the French Quarter, downtown streetcars and the Riverwalk shopping district along the Mississippi. Elegant historic homes of the Garden District and French Quarter open their doors in December for holiday home tours. It’s a rare chance to peek inside these antebellum charmers, decked out in holiday finery.

NEA member travel benefits: Through the NEA Travel Program, you can search for deals on flights to Louis Armstrong New Orleans International Airport (MSY). Look for affordable lodging options such as Le Pavillon New Orleans, a four-star, centrally located boutique hotel which averages just $95 a night. To be in the French Quarter, try the Astor Crowne Plaza New Orleans French Quarter, which has spacious rooms and a pool for an average of $102 a night.

Plan your itinerary: Visit New Orleans | Explore Louisiana

Breckenridge, Colorado

Dreaming of a white Christmas? The odds are good in this mountain resort community, which sits high in the Colorado Rockies at 9,600 feet. The historic gold and silver mining town 80 miles west of Denver looks more picturesque than ever during the holidays. Opening day of the Breckenridge Ski Resort, usually in mid-November, kicks off the holiday celebrations here.

On the first weekend in December, hundreds of Santas race down Breckenridge’s Main Street, followed by a Bernese Mountain Dog parade, the arrival of Santa Claus by horse-drawn carriage and the lighting of the town tree. The Breckenridge Arts District hosts a Handmade Holiday Market, with music, artists’ demonstrations and a variety of affordable craft items for holiday shopping.

Breckenridge rings in the New Year with activities in town and on the mountain. The “glow worm parade” kicks off the evening, with kids ages 5–13 skiing down a beginner slope with glow sticks. Then comes the long-standing torchlight parade down the ski slopes, along with parties in town and fireworks visible from the Blue River Plaza. Early risers on New Year’s Day can often enjoy uncrowded slopes.

NEA member travel benefits: Book a flight via NEA Travel: Flights into Denver International Airport (DEN), about 95 miles away, to earn NEA Travel Dollars. Then, check for hotel deals to stay at accommodations such as the chalet-style the Lodge at Breckenridge, which includes a free daily breakfast, for an average of $158/night, or to earn or spend your Hilton Honors rewards, book a room at DoubleTree by Hilton Hotel Breckenridge, which has king room with sofa bed for an average of $167/night, and includes a pool and gym.

Plan your itinerary: Go Breck | Colorado.com

Plan your holiday getaway today