Though temperatures may be dropping, Chicago is heating up with plenty of holiday and winter experiences to enjoy, whether visiting over a weekend or staying throughout the festive season. Chicago was once again designated by Condé Nast Traveler’s readers as the Best Big City in the U.S. in 2021 for the fifth year in a row, so there's no better time to visit than this winter. For plenty of information and holiday ideas, visit ChooseChicago.com.

Festive Attractions + Programming:

This season, visit the traditional Christkindlmarket at Daley Plaza (celebrating its 25th anniversary this year) for a mug of glühwein and that perfect handcrafted gift. Then lace up your skates and zip around The Peninsula Sky Rink (the only hotel skating rink in Chicago) followed by a traditional Holiday Afternoon Tea in The Lobby beneath the 6-metre (20-foot) Christmas tree. Marvel at the thousands of twinkling lights on display at ZooLights and Illumination at The Morton Arboretum or the dozens of festively decorated trees at the MSI’s Christmas Around the World display. Or head over to Navy Pier’s new "Light Up the Lake", an indoor, temperature controlled experience featuring large-scale light-sculpture displays, a regulation-size Alpine ice rink, authentic holiday beer garden, Santa’s Village and more. Winterland at Gallagher Way will extend its festivities beyond the holiday season with ice bumper cars, skating lessons and curling lessons running through January/February 2022 and the popular Maggie Daley Ice Skating Ribbon will return with a fun new collaboration with the blockbuster art experience Immersive Van Gogh, projecting visuals of sunflowers and starry night brush strokes onto the ice. 

Hotel News + Holiday Packages:

A series of Yuletide specials this holiday season at The Langham Chicago (available through January 2, 2022) include the Oh Christmas Tree package featuring a decorated Christmas tree in-room, deconstructed champagne cocktails and more beginning at USD $1,100, Dive into the Season including lavish guest room accommodations and exclusive access to Chuan Spa's indoor pool and holiday-themed floats; beginning at USD $825, or splurge on A Signature Christmas in a floor-to-ceiling window suite featuring panoramic views of Chicago, an in-residence dinner prepared by Executive Chef Damion Henry and a custom-designed holiday tree plus much more. (Rates start at USD $13,525.)

At The Peninsula Chicago, holiday packages like the Holly Jolly Family Holiday Package and Merry and Bright Couple's Holiday Package include amenities such as an in-room holiday tree or Menorah, holiday welcome amenity or bottle of wine/Champagne upon arrival, access to a library of holiday themed movies, a USD $100 gift card to the nearby Neiman Marcus Michigan Avenue store and more. Rates start at USD $1,250, with packages available through December 31, 2021.

For the eighth consecutive year, Swissôtel Chicago’s Presidential Suite will be transformed into Santa’s home-away-from-the-Pole for the holiday season, welcoming Chicagoans and visitors alike. The Santa Suite offers sweeping views of the city and is filled with 17 Christmas trees, festive decor, games and holiday craft kits, cookie decorating stations, "Letter to Santa" packs, and more. Book the Holiday Penthouse Hideaway through December 26, 2021, from USD $1,500 per night. 

And stay tuned this spring for the long-awaited opening of the St. Regis Chicago, in Chicago’s newest skyscraper, the third-tallest building in Chicago designed by renowned architect Jeanne Gang, with signature restaurants concepted by the award-winning Alinea Group.

Restaurants + Dining:

Gordon Ramsay Burger, a new concept from the celebrity chef and restaurateur, will open in the city’s River North neighbourhood in late 2021 or early 2022. The Chicago location, which will be equipped with an island bar and seating for 120, will be the second Gordon Ramsay Burger location in the U.S, and the chef’s first restaurant in Chicago. 

Kitchen United MIX, a to-go food hall, is opening a second Chicago location in the former Wells St. Market. Kitchen United MIX is the nation’s first “Multi-Restaurant Ordering” to-go experience, the only destination that allows foodie fans who love variety to order meals from 10+ restaurants, all on the same bill. The new facility houses restaurant brands including Hawaiian Bros, Greenleaf, Siri Indian Express, Trejo’s Tacos, Dog Haus, Plant B and more. 

New York food hall Urbanspace will open two Chicago locations, the city's first new food hall since the pandemic. Urbanspace West Washington recently opened while a second location, inside Willis Tower, is projected to open in Winter 2022. 

Chicago Restaurant Week returns March 25 - April 10, 2022.

Museums + Art Exhibitions:

The Art Institute of Chicago has a full Fall 2021/Winter 2022 schedule, featuring the exhibits: André Kertész: Postcards from Paris (Until January 17, 2022), BARBARA KRUGER: THINKING OF YOU. I MEAN ME. I MEAN YOU (Until January 24, 2022), Hito Steyerl: Is the Museum a Battlefield? (Until January 24, 2022), Mimi Cherono Ng’ok: Closer to the Earth, Closer to My Own Body (Until February 7, 2022), Life and Afterlife in Ancient Egypt (Opening February 11, 2022) and more.

Chicago History Museum’s newest permanent exhibition City on Fire: Chicago 1871 guides visitors through the crucial events and conditions before, during and after the fire which overwhelmed Chicago for three days, submerging a city built of wood and causing severe destruction and homelessness and inflaming tensions against the immigrant Irish O’Leary family. 

The Field Museum’s newest exhibit Wild Color (running through January 8, 2023) features immersive rooms, each representing a color of the rainbow. In Wild Color, examine some of the brightest and boldest examples alongside experiences designed to awaken your senses. 

Chicago’s Museum of Contemporary Art has a busy Fall 2021/Winter 2022 schedule, featuring the exhibits: Alfredo Jaar: The Structure of Images (Until January 9, 2022), Andrea Bowers (Until March 27, 2022), Chicago Works: Caroline Kent (Until April 3, 2022) and more. Coming in Spring 2022, MCA will present the first career-spanning retrospective of the internationally renowned Chicagoan Nick Cave in an exhibition titled NICK CAVE: FOROTHERMORE (May 14–Oct 2, 2022). 

Rise Up: Stonewall and the LGBTQ Rights Movement, the newest special exhibition at the Illinois Holocaust Museum and Education Center running through May 8, 2022, explores the June 1969 police raid of the Stonewall Inn as the flashpoint that ignited the modern gay rights movement in the United States.

EXPO Chicago, the international exhibition of contemporary and modern art will be held at Navy Pier in April 2022.

Attractions + Developments:

The Obama Presidential Center broke ground this fall in Jackson Park; this amazing world-class museum will bring a spectacular new campus to Chicago’s South Side and provide a fabulous new gathering space for the Hyde Park community and residents. Upon completion, it will feature a museum, library, park and activity center, women’s garden and so much more.

Skydeck Chicago at Willis Tower has reopened after completing an extensive redevelopment encompassing the attraction’s lower level, delivering an interactive experience that celebrates the unique personality, history, neighbourhoods and sites of Chicago. This immersive, Chicago-themed museum features modern physical and visual displays, educating guests of all ages on the city's history, culture, cuisine and architecture through interactive and informative experiences. Guests are invited to leave a mark on the city by creating drawings or messages on the interactive sequin wall. 

Theatre + Performing Arts:

Indoors, the stages of Chicago’s theatres are once again lighting up after more than a year of darkness with a slew of new performances that capture Chicago's creative spirit, including the Broadway-bound Paradise Square, the North American tours of Disney's Frozen, Pretty Woman: The Musical, Moulin Rouge! The Musical and more. The Steppenwolf Theatre Company, which recently reopened with a new USD $54 million arts and education center (including a theatre-in-the-round) will welcome the world-premiere of King James, an intimate exploration of the place sports and athletes (like “King” LeBron James) occupy in our emotional lives and relationships, while Chicago Shakespeare Theatre on Navy Pier will premiere the Broadway-bound musical The Notebook, based on the best-selling novel by Nicholas Sparks. 

Chicago Theatre Week will return from February 17-27, 2022 featuring more than 100 performances, from musicals to improv, dramas and beyond. 

The Joffrey Ballet kicks off its first performance of 2022 with Yuri Possokhov’s fresh interpretation of this revered ballet classic Don Quixote (February 16-27, 2022), a tale of bravery, fantasy and love centring on an aging and eccentric nobleman who imagines himself to be a valiant knight. 

The celebrated Steppenwolf Theatre Company returns after a 20 month intermission, with the opening of the USD $54 million Liz and Eric Lefkofsky Arts and Education Center, which includes the Ensemble Theater in Honor of Helen Zell, an intimate state-of-the-art 400-seat theater in the round, and is topped off by The Loft, an arts and education center for young performers. This new performance venue will open to audiences with the Steppenwolf for Young Adults world premiere adaptation of Eve L. Ewing’s 1919 from February 1-March 5, 2022. 

Conceived by Chef Rick Bayless and Windy City Playhouse's artistic team, A RECIPE FOR DISASTER is a live experience staged at nearby restaurant Petterino’s that combines immersive theater, food, and farce. Guests are invited inside the restaurant to join us for "influencer night." Admission also includes six bite-sized tastings by Chef Rick Bayless, one cocktail sampling from Lanie Bayless, and two wine pairings. Tickets currently available through the end of March 2022.