Think Chicago this holiday season: cold is good!
Let’s hear it for Chicago! The Windy City has just been named one of the best places to go in 2026 by Frommer’s. And for the ninth consecutive year, Chicago was recently voted the Best Big City in the U.S. by readers of Conde Nast Traveler.
That certainly includes the holiday season and winter. Chicagoans never let the cold cramp their style. There are holiday markets and spectacular light displays, culinary celebrations (Chicago Restaurant Week Jan. 23-Feb 8) , Chicago Theatre week (Feb. 4-15) , Chicago Auto Show (Feb. 7-16) and much more with the world-class museums and terrific smaller ones.
The lakefront Museum Campus, home to iconic spots like the Field Museum, Adler Planetarium, and the Shedd Aquarium; Also near downtown, you’ll find the Art Institute of Chicago — one of the country’s oldest and largest art museums. All have terrific family programs.
The Griffin Museum of Science and Industry presents Marvel’s Spider-Man: Beyond Amazing – The Exhibition (through February 8, 2026) with rare comic books, props and costumes from Spider-Man movies, cutting-edge interactive installations, and the chance to take selfies with life-size statues of favorite characters.
Chicago’s free Lincoln Park Zoo is open for exploration 365 days a year. In the colder months, you can admire majestic polar bears, penguins, and snow monkeys as they play outside.
Bundle up and take a walk along frozen Lake Michigan on the Lakefront Trail.
Get an amazing view from the Skydeck at Willis Tower where you can stand at 1,353 feet above the city. The Ledge features glass balconies that extend more than 4 feet! Don’t miss the interactive museum at the Willis Center, which is a combination history museum, children’s museum and more.
Take a free tour led by a local with Chicago Greeter in a neighborhood of your choice or a free hour-long guided walk with Instagreeter that doesn’t require reservations.
Sample deep dish Chicago pizza, a Chicago-style hot dog, Italian beef sandwich, Flaming Saganaki, in Greektown a Greek-style fried cheese, and Garrett Mix popcorn, a popular mix of cheddar and caramel popcorn. Have a brownie where they were invented at the Palmer House for the 1893 Chicago World’s Fair. Of course, there are plenty of places for steaks and other upscale offerings.
Foodies whatever their ages won’t want to miss Chicago Restaurant Week when hundreds of restaurants offer special prix fixe menus for lunch, brunch, and dinner. Theater lovers come for Chicago Theatre Week for value priced tickets starting at less than $15.
Whatever the weather, visitors must pose in Millennium Park at the huge 33 feet high Cloud Gate sculpture (It weighs 110 tons!) affectionately dubbed “the Bean” for its shape. The huge sculpture, one of the world’s largest permanent outdoor art installations, is one of Chicago’s most popular sights and reflects the people moving around and the city’s famous skyline. Come skate here at the free rink!
On the Chicago River, rent a hot tub boat from Chicago Boat Company. These one-a-kind BYOB vessels fit six people and are a unique way to admire the city’s skyscraper-lined Riverwalk.
Kids will love the Four Seasons Chicago’s mascot for kids, Sammy the Skyscraper (Chicago is recognized not only for its skyline but for some of the tallest buildings in the country, partly as a result that destroyed much of central Chicago in 1871 with the new building ushering in the steel-frame skyscraper era
Chicago holiday traditions as the Magnificent Mile Lights Festival, Chicago Christkindlmarket, Lincoln Park’s ZooLights, The Joffrey Ballet’s performance of The Nutcracker, and a new season of creative holiday pop-ups!
Navy Pier’s Winter WonderFest offers everything from ice skating, 30+ dining options, local artists and performers, a kid-friendly carousel and Arctic Express Train to the Polar Extreme obstacle course, rides on the iconic Centennial Ferris Wheel and even visits from Santa. You can also visit the Chicago Children’s Museum at Navy Pier.
The LaSalle Chicago, Autograph Collection returns as the official hotel partner of Christkindlmarket Chicago 2025. Just four blocks from Daley Plaza, guests can cozy up in refined comfort and enjoy a special holiday package that includes Glühwein drink vouchers, collectible market mugs, and a luxurious stay
There are plenty of opportunities to give back in Chicago this holiday season as well as connect with one another.
The St. Regis Chicago has launched its new Family Traditions Package, where families are invited to embrace a curated journey of connection, creativity, and comfort from the moment they arrive. Children are greeted with handcrafted amenities and monogrammed robes, and access to the Astor Treasure Chest—a whimsical trove filled with curated board games, books, and sweet surprises inspired by the St. Regis legacy. During the holidays from Dec 10-21, guests can experience the art of champagne sabering and meet Santa. Drop off outgrown coats for the nonprofit Cradles to Crayons.
At Chicago’s Hotel EMC2, guests are invited to Share a Story, Light the Season in partnership with Books4Cause, a Chicago-based social venture dedicated to expanding access to books and education worldwide. From November 18 through December 31, guests who bring a gently used book to donate at the Albert, will receive a complimentary glass of wine in return. Place the books under the hotel’s big holiday tree.
Just don’t forget your hat and gloves!