A 2026 Chicago Guide to the Holiday Season: Where to eat, sleep, shop, and be festive
The festive season in Chicago is nothing short of enchanting, and Fairmont Chicago, Millennium Park is the perfect place to experience it all. Ideally situated in the heart of downtown, our luxury hotel places you close to the city’s most beloved holiday traditions, attractions and seasonal celebrations. From sparkling city lights and charming Christmas markets to outdoor ice skating and festive dining, discover the magic of the season at every turn.
Whether you’re planning a family Christmas vacation, a festive escape with friends, or a romantic winter getaway, enjoy easy access to iconic attractions including Millennium Park, Maggie Daley Park and Chicago’s renowned shopping destinations. Explore the best things to see and do in Chicago this holiday season, with a memorable stay at Fairmont Chicago as your home base.
Skate Beneath the City Lights
Embrace the winter with a visit to the Maggie Daley Park Ice Skating Ribbon. Just steps from the hotel, this winding outdoor skating path offers a memorable way to take in Chicago’s spectacular skyline. From November 13, 2026, through March 7, 2027, skaters can glide along its winding, quarter-mile path, surrounded by city views and winter scenery. The Ribbon is a must-visit for families, couples and winter enthusiasts alike.
For another seasonal spectacle, head to the Magnificent Mile Lights Festival on November 21, 2026, and watch one of Chicago’s most iconic shopping districts illuminate with holiday cheer.
After a day exploring the city, return to Fairmont Chicago to warm up with a seasonal cocktail and festive bites at the Lobby Bar, or savour the vibrant Latin-inspired cuisine of Toro Chicago.
Explore Chicago’s Beloved Holiday Markets
Experience the charm of a European Christmas at Christkindlmarket, one of Chicago’s most treasured holiday traditions, now in its 30th year. Running from November 20 through December 24, 2026, the market invites visitors to browse festive wooden chalets filled with handcrafted gifts, unique ornaments and seasonal treats. Sip traditional glühwein, sample sweet and savoury specialties, and find the perfect keepsake to remember your Chicago holiday.
For another magical seasonal outing, visit Lincoln Park ZooLights, returning November 20, 2026, through January 3, 2027. Wander illuminated pathways and admire dazzling light displays for an enchanting evening that guests of all ages will enjoy.
With the city’s festive attractions within easy reach, Fairmont Chicago is an ideal home base for discovering the season’s most memorable experiences.
Shop the Season in Style
Whether you are searching for thoughtful gifts, indulging in a little seasonal shopping or simply enjoying the festive atmosphere, downtown Chicago offers something for every style. Explore the luxury boutiques and renowned flagship stores along the Magnificent Mile, or discover the department stores and distinctive shops of State Street. Afterward, retreat to the comfort of your spacious guestroom before heading out for an evening of holiday dining and entertainment.
Savour the Flavours of the Festive Season
At Fairmont Chicago, the joy of the holidays extends to the table. From November 19, 2026, through January 3, 2027, celebrate with festive flavors at Toro Chicago and the Lobby Bar. Discover a seasonal selection of handcrafted cocktails, warming winter favourites and festive bites, thoughtfully created for gathering with family and friends.
Throughout November and December, the Lobby Bar also welcomes local pianist Steve Gonzalez on Thursday and Friday evenings from 6 to 9 p.m. Settle in beneath the holiday lights, enjoy live music and savour a seasonal cocktail in a warm, inviting atmosphere.
For those looking to explore something new, join the hotel’s House Sommelier for complimentary wine tastings on select Thursdays in November and December, from 5 to 6 p.m., with the purchase of a glass of wine or equivalent. It is a perfect opportunity to discover new favourites and add a special touch to your festive evening.
Whether you are planning a romantic winter escape, a family holiday or a festive celebration with friends, Fairmont Chicago, Millennium Park combines a prime downtown location, exceptional dining and memorable seasonal experiences. Make your holiday getaway even more special with the Festive at Fairmont package, featuring a special festive amenity and early check-in and late check-out.
Planning to welcome 2027 in style? Celebrate at the Toro Chicago New Year’s Eve Party, featuring Latin-inspired bites, live entertainment, dancing and a midnight Champagne toast.
Book the Festive at Fairmont package and discover the Toro Chicago NYE Party to make this holiday season unforgettable.
