Chicago on a Winter’s Day


The list of amazing things to do in Chicago this winter is almost as long as the season itself. And, it more than makes up for the occasional polar vortex.

Things To Do

Millennium Park

Millennium Park is your kind of town square, home of the sculpture officially called Cloud Gate—aka The Bean. In winter, the park’s most popular winter activity is the ice skating rink which operates for four months a year. Another popular winter happening is Caroling at Cloud Gate, billed as part concert, part sing-along during the holidays. No matter the season, swing by the Park Grill restaurant in the heart of the park for beautifully plated American cuisine.

Navy Pier

The Centennial Wheel dominates the scenery at the state’s most popular draw, but there are plenty of other gems to discover here, too, including a gallery of stained glass and Amazing Chicago’s Funhouse Maze. While admission to Navy Pier is free, note that fees are charged for individual experiences.

360 Chicago & The Ledge

Lean into winter with TILT at 360 Chicago as you take a deep breath and experience the thrill of a new perspective on the snow-covered city. Also, don't look down! (or do...that's sort of the point) at The Ledge, glass boxes offering unparalleled views of Chicago and four neighboring states. 

Museum Campus

You can easily fill a day hopping among the world-class museums dotting this park along Lake Michigan: the Shedd Aquarium and the Field Museum of Natural History. Illinois residents receive free admission on select days (check individual websites for details).

Skating Ribbon at Maggie Daley Park

Think outside the rink when it comes to ice skating, this winding quarter-mile track offers gentle curves and rises, perfect for skaters hoping to simultaneously bask in city views. 

National Museum of Mexican Art

With an 8,500-piece collection, spanning over 3,000 years of history on both sides of the border, and the only Latinx museum accredited by the American Alliance of Museums, The National Museum of Mexican Art is a cultural treasure, located in the heart of the city’s Mexican community.

The Oriental Institute, University of Chicago 

Browse artifacts from the ancient Near East, including Egypt, Persia, Syria and Nubia. Exhibits range from towering statues of King Tut to tiny fragments of the Qur'an and a child's pull toy from 2350 BC. 

Lincoln Park Zoo

Walk on the wild side—from aardvark to zebra—in the shadows of the skyline. It’s one of the nation’s few free zoos.

Revolution Brewing

Escape the wintery chill for a beer at Revolution Brewing. This converted warehouse has barrel wood walls and benches made from 100-year-old beam salvaged during construction. Hand-crafted food from the kitchen includes everything from farm-raised pork to plenty of vegetarian dishes.

Gino's East

Taste a Chicago deep-dish classic pizza at Gino's East, featuring a thick, golden "secret" recipe crust loaded with fresh mozzarella and chunky vine-ripened tomato sauce. 

Lincoln Park Conservatory

Located adjacent to the Lincoln Park Zoo, temporarily duck out of the snow with towering palms, ancient ferns and exotic orchids thrive in a charming Victorian-era glass house.

Garfield Park Conservatory

For a similar and delightful tropical activity, experience a greenhouse effect at this world-class indoor paradise of plants across 12 acres—the 3rd largest garden under glass in the world.

Clarke House Museum

History enthusiasts will rejoice over the city’s oldest home, an 1836 Greek Revival, which today sits in a park and shows how a pre-Civil War middle-class family lived.

Money Museum at the Federal Reserve Bank of Chicago  

Stop in at this museum in Chicago’s financial district to take pictures with $1 million, learn how to detect fake bills and catch up on the history of U.S. currency. Temporarily closed, virtual programs available. 

The Art Institute of Chicago

Hey, parents of budding artists: Admission is always free for kids 13 and younger. Architecture, medieval armor, photography, European sculptures and Impressionist art are just a few of the collections inside the eight-building complex in the heart of the city.

Smyth Restaurant

For a unique culinary experience combining warmth, vitality and artistry, look no further than Smyth. The restaurant features an open kitchen surrounded by intimate tables and a cozy living room-style lounge. They offer 3 different prix-fixe menu experiences.

Chicago Cultural Center 

The world’s largest Louis Comfort Tiffany dome, composed of 30,000 stained-glass pieces, crowns the neoclassical 1897 Chicago Cultural Center (free tours offered). Also, enjoy complimentary concerts, performances, films and art exhibits. 

Chicago Theatre Week

During Chicago Theatre Week, many of the city’s 250 theaters offer steep discounts on tickets (as low as $15) for their productions. It’s all to celebrate Chicago’s world-class theater scene. After celebrating 10 years in 2022, this initiative allows visitors and residents to sample an extraordinary range of theatrical offerings, from musicals to improv to dramas and beyond. 

When it isn’t theater week, you can score half-price seats a day or two before showtime via or in person at one of two downtown locations (72 E. Randolph St. and 108 N. State St.).

Hotel Deals

Swissôtel Chicago 

The Swissôtel makes it easy to give back while getting a good night’s rest with the Trees of Hope package, available through the holiday period to January 11.

The Peninsula Chicago

With so much to pack into a Windy City getaway, staying two nights simply isn’t enough. Get your third night for free when you book the More Time…With Our Compliments package.

All discounts and package offers are subject to change and may not be available during identical periods each year. They may be discontinued at any time.