A three-day itinerary for a cozy winter getaway to Chicago

If you’re looking for a getaway in January or February, Chicago continues to deliver a flurry of seasonal fun long after the holidays end.

Between ice skating under the city lights and catching a show on a snowy evening, a winter trip to Chicago turns cold days into warm memories.

Embrace the new year by planning your trip around top winter events, including the 15th annual Chicago Theatre Week, the 20th annual Chicago Restaurant Week, the Chicago Auto Show, and more.

Here’s our guide to planning a magical winter getaway in the country’s Best Big City with top experiences, neighborhood gems, and more.

Day 1: Classic Chicago experiences

Top experiences:

• Art Institute of Chicago
• Skating in Millennium Park
• Winter rooftop bars
• Broadway in Chicago

Your first stop is the downtown Millennium Park Campus, home to some of Chicago’s most recognizable landmarks and attractions.

Start your day at the adjacent Art Institute of Chicago, one of the country’s oldest and largest art museums. The permanent collection features roughly 300,000 pieces of art, including the renowned Impressionism gallery, plus a rotating array of special exhibitions.

Afterward, bundle back up and make your way to Millennium Park for ice skating. Enjoy a spin on the ice at the iconic McCormick Tribune skating rink beneath Cloud Gate (also known as “The Bean”). Another popular spot is Maggie Daley Park’s quarter-mile-long Skating Ribbon, which winds between snow-covered evergreens.

When it’s time to grab a bite, across the street to the historic Chicago Athletic Association. Tucked away on the second floor, the Drawing Room is an ornate vintage space accented by dark wood and leather furnishings. Grab a spot by one of the three crackling fireplaces and enjoy the cozy atmosphere.

Stop by one of Chicago’s winter rooftop bars, where you can hide away in an igloo, warm your hands beside a fire, or play a round of curling. Whether you’re sipping seasonal cocktails at The Gwen’s rooftop terrace or admiring the skyline views at LH Rooftop, Chicago has a wintery bar for just about every mood.

End your evening at the theatre. Broadway in Chicago’s winter lineup includes the Tony-winning rom-com Maybe Happy Ending and smash-hit Oh, Mary!, a gleefully absurd comedy about Mary Todd Lincoln. Or see what’s playing at the city’s neighborhood theatres.

Day 2: A day of art and culture

Top experiences:

• Art and history museums 
• Elegant high tea
• Warm and welcoming dining

Set aside a full day for Chicago’s South Side, a collection of historic neighborhoods filled with hidden gems for art and culture lovers. Spend the morning exploring one of the area’s acclaimed museums, from a massive science center to intimate art galleries.

Delve into Black history, art, and culture from Chicago and around the world at the DuSable Black History Museum and Education Center in Washington Park.

The free Smart Museum of Art features galleries spanning historical and contemporary works, with rotating exhibitions that give you a reason to come back.

If you’re lucky enough to snag tickets, you can explore the new Obama Presidential Center. But even without a ticket, there’s plenty to see and do on the campus. Admire public art, try Obama family recipes, and soak in snow-dusted city views from the Sky Room (limited free tickets are available on a first-come, first-served basis).

In the afternoon, head to the Stony Island Arts Bank. This stunning bank building was once in disrepair but has been lovingly restored and transformed into a community arts space.

Browse the collections and exhibitions, then settle in for a drink or bite to eat. Make reservations for a unique high tea experience at the Korean-inspired Han Cha, or sample creative cocktails and natural wine at Yunomi, a walk-in bar and lounge.

Afterward, stroll through the University of Chicago campus, home to dramatic Gothic buildings that appear even more majestic under the snow. Notable points of interest include the Rockefeller Chapel and the Harper Memorial Library’s grand reading room.

From late November to mid-February, you can skate at the nearby Midway Plaisance ice rink, located on the site of the 1893 World’s Fair. Admission to the rink is free, with skates available to rent for a small fee.

Round out the day in Hyde Park with dinner at Virtue Restaurant & Bar, a James Beard Award-winning kitchen that specializes in Southern cooking. Or enjoy bold flavors from across the African diaspora at welcoming Mahari.

Day 3: Cozy and quirky vibes

Top experiences:

• Lincoln Park Conservatory 
• Local shopping and dining
• Chicago Magic Lounge 

Start your morning in charming Lincoln Park with a sweet French toast flight at Batter & Berries or house-made pastries and Mediterranean dishes at Cafe Yaya.

After brunch, pop into the Lincoln Park Conservatory. The Victorian-era greenhouse provides a delightful dose of greenery in the middle of winter. Admission is free, but book a timed ticket in advance. Right next door, Lincoln Park Zoo is also free year-round. The zoo’s lakefront grounds are particularly beautiful on a frosty day.

Next, spend the afternoon on Clark Street in the quirky Andersonville neighborhood. Lined with unique boutiques and colorful storefronts, this area is known as a mecca for cozy local shopping and dining.

Pick up Chicago-inspired gear and accessories at Transit Tees, then leaf through whimsical stationery, art, and gifts at Foursided. Drop by Cowboys and Astronauts, a pleasantly offbeat store stocked with lifestyle goods and apparel.

After shopping, pop into Simon’s Tavern to warm up with hot glögg, a Scandinavian beverage made with mulled wine or spiced spirits. Also on Clark Street, the Swedish American Museum traces the history of Chicago’s Swedish community.

As the day winds down, grab tickets to the Chicago Magic Lounge. The speakeasy-style venue is hidden inside an old-fashioned laundromat. A rotating cast of magicians performs close-up tricks before taking the stage for astonishing performances.

Afterward, enjoy a nightcap at Nobody’s Darling, an acclaimed cocktail bar that celebrates trailblazing women of color, or Marty’s Martini Bar, an intimate and inclusive LGBTQ+ lounge that’s been pouring a proper martini for more than two decades.

Find more things to do and see in Chicago this winter.