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Chicago in Winter (Best Things to Do + 3-Day Itinerary!)

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January 28, 2022

If you’re looking for the ultimate guide to visiting Chicago in winter – look no further, we’ve got you covered!

With its plethora of fun, year-round activities, world-class museums, and some of the most iconic foods in North America, it’s unsurprising that tourists continue to flock to Chicago in winter despite the snow and cold.

In this post, we’ll tell you all about our favorite winter activities in Chicago and show you how to incorporate them into a complete Chicago 3-day itinerary.

Along with including the city’s most exciting year-round offerings, we’ll share our detailed packing list to keep you shielded from Chicago’s winter weather.

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A perfect 3-day Chicago itinerary when visiting Chicago in winter, from top US family travel blog, Travel With A Plan!
A view of Downtown Chicago in winter

Chicago in Winter

Located on the shore of Lake Michigan in Midwest USA, Chicago, Illinois is a glorious city with a population of 3 million people.

Chicago is a tourist’s dream as it has a magnificent, walkable downtown area filled with gorgeous parks and sculptures, impressive museums, several famous Chicago foods, and beautiful lakeside views.

Perfectly blending the hustle and bustle of city life with a degree of friendliness that you’d expect from a small town, this diverse area is a must-visit metropolitan wonder.

Despite having 4 distinct seasons and climates, Chicago is truly a city that can be enjoyed during each and every month of the year.

In fact, though our whole family absolutely loves our Chicago summer itinerary, we find that visiting Chicago in winter is just as spectacular.

Things to Do in Chicago in Winter

Before your visit to Chicago, be sure to check what Public Health Orders are in place regarding face coverings and vaccination status in public places.

If you’re familiar with popular urban vacation destinations, it’s more than likely that Chicago is on your US bucket list!

Whether you’ve dreamed of ice skating in Millennium Park and photographing “The Bean” or you want to
enlighten your kids by checking out the ever-popular Adler Planetarium, there are infinite things to do in Chicago during winter.

Though it’s not possible to mention everything there is to do in Chicago during winter, we’ve handpicked a selection of must-do activities that you shouldn’t miss out on while you’re in the Windy City!

Oh, and psst…we LOVE Chicago so much that we’ve written several other guides to help you plan your trip!

Chicago's Magnificent Mile in winter
Strolling on Magnificent Mile

1. Browse and Shop Magnificent Mile

Chicago’s Magnificent Mile is a 13-block stretch of shopping, dining, restaurants, hotels, and attractions.

Found in the heart of Downtown Chicago on North Michigan Avenue, you will find 460 stores, 275 restaurants, 60 hotels, as well as unique entertainment options sprinkled throughout its length.

Magnificent Mile has a classic metropolitan buzz and is especially festive during the winter as its trees are lit up with thousands of twinkling white lights.

The sidewalks are always promptly cleared of snow during the winter so that visitors and locals can continue to explore the Mile between browsing its indoor shops.

Our favorite things to do on Magnificent Mile include visiting the 360 Chicago Observation Deck, going to The Disney Store, Dylan’s Candy Bar, and American Girl Place, as well as admiring the spectacular architecture.

A perfect 3-day Chicago itinerary when visiting Chicago in winter, from top US family travel blog, Travel With A Plan!
The Bean in Millenium Park

2. Visit Millennium Park

Millennium Park is the epicenter of fun in Chicago as this is where you’ll find Cloud Gate (“The Bean”), Crown Fountain, Maggie Daley Park, and the unique BP Pedestrian Bridge.

Though you won’t get to experience its green space or feel the splash from Crown Fountain when visiting Millennium Park in winter, it’s still a must-visit in Chicago even when the temps are cold.

You’ll still find hundreds of visitors snapping family photos and selfies next to The Bean (quite possibly dusted with beautiful snow!), as well as touring the Art Institute of Chicago and marveling at the Chicago Christmas Tree.

Additional planning tip: If you’re looking to warm up indoors, grab a bit to eat, AND have some fun, head across the street from Millenium Park to the Chicago Athletic Hotel.

Here, you’ll find The Game Room (restaurant, bar, built-in bocce bay, billiards, shuffleboard, chess, and checkers tables), as well as TopGolf Swing Suites that can be rented by the hour.

Our kids (who are sports fanatics) loved the sports/golf simulator room and the fact that we could order food and drinks right to the suite.

3. Go Ice Skating

Though I’m not familiar with sledding in Chicago, one of the best things to do during winter in Chicago is to go ice skating!

Chicago has a multitude of seasonal ice skating rinks that pop up around the city during its winter months offering fun and enjoyment to both locals and visitors alike.

Most rinks are open mid-November through March, weather permitting.

Skate rentals are available, or guests are welcome to bring their own.

Here’s a list of the best places to go ice skating in Chicago:

  • McCormick Tribune Ice Rink (Classic outdoor ice skating rink; located in Millennium Park with The Bean sculpture right in the background.)
  • Maggie Daley Ice Skating Ribbon (A curvy ice-skating path that is twice the length of a lap around a traditional skating rink; located in Millenium Park near Maggie Daley Park.)
  • Light Up the Lake at Navy Pier (Indoor ice skating rink located at Navy Pier that is typically only open from the end of November through January 2nd.)
  • Winterland at Gallagher Way (Classic outdoor ice skating rink located at Wrigley Field that offers skating, curling, and ice bumper cars; typically only open from the end of November through the end of February.)
  • Sky Rink at Peninsula Chicago (The only hotel ice skating rink in the city; located on a 4th-floor terrace overlooking Michigan Avenue.)

Additional planning tip: Going ice skating tops our list as one of the best things to do in Chicago at night!

The rinks stay open late and are illuminated with colorful lights once darkness fills the sky.

Navy Pier Chicago in winter

4. Go to Navy Pier | Ride the Centennial Wheel

There are so many awesome attractions at Navy Pier Chicago, and most of them are open year-round!

Despite the gray skies and floating ice chunks, the harbor of Lake Michigan in which Navy Pier sits is surprisingly beautiful and serene in the winter!

Plus, all of the shops and delicious dining venues throughout the pier remain open, as does Chicago’s famous Ferris wheel, the Centennial Wheel!

Don’t miss out on a chance to ride the Centennial Wheel in its climate-controlled gondolas that makes for an especially comfortable winter ride.

This is the best way to see the Chicago skyline at night!

5. Enjoy Famous Chicago Foods

Call them iconic, there are several signature Chicago dishes to enjoy throughout the city no matter what month of the year you visit.

Whether you’re a culinary enthusiast or a foodie newbie, spend winter in Chicago enjoying a Chicago hot dog, Chicago-style deep dish pizza, an Italian Beef sandwich, fried chicken, or Garrett Popcorn!

6. Attend a Broadway Show

Chicago has a booming arts scene!

If you’re visiting Chicago during winter, be sure to check out the several theaters located throughout Chicago in which guests can watch Broadway-caliber musicals and shows.

Indoor theatrical performances are an awesome activity to do in the winter and this is an experience that both kids and adults will love if you choose the right show.

Check out Chicago’s Theater in Chicago website to find venues, performances, running dates, and showtimes.

A perfect 3-day Chicago itinerary when visiting Chicago in winter, from top US family travel blog, Travel With A Plan!
The view from Skydeck Chicago at the top of Willis Tower

7. Visit the Willis Tower

If you’re looking for indoor winter activities in Chicago, be sure to visit the Willis Tower.

The Willis Tower is Chicago’s tallest skyscraper – you literally cannot miss it!

The best part about the Willis Tower is that visitors to Chicago can actually get up-close and personal with this iconic 110-story building.

On the bottom 5-levels of the building is a brand new trendy shopping and dining area called Catalog.

Eating venues here include Shake Shack, Brown Bag Seafood Co., DoRite Donuts, and our favorite, Tortazo (Modern Mexican flavors, fountain Margaritas, and top-notch customer service!).

After dining, head downstairs to visit Skydeck Chicago – an absolute must-do Chicago activity!

A ticket to visit Skydeck includes a 30-60 minute interactive queue area where visitors can learn all about “the best of” Chicago.

Afterward is the elevator ride up to the 103rd floor of the Willis Tower where the most spectacular views of the city await.

Not only that, but you’ll also have an opportunity to stand and take photos on The Ledge, which is a glass balcony that extends four feet outside the walls of the building.

Being suspended over the city in this way is both terrifying and amazing at the same time!

Skydeck Chciago in winter
Our family on The Ledge at Skydeck Chicago

8. Seek Out a Pop-Up Experience

One of the best things to do in Chicago this winter is to visit one of Downtown Chicago’s pop-up experiences.

These interactive experiences set up a ‘museum’ of sorts that showcases an imaginative and immersive look into popular TV shows, storybooks, and other interesting topics.

During our visit to Chicago in winter, we had the chance to visit the Dr. Seuss Experience and The Office Experience.

Also in town was the Van Gogh Experience, which we were unable to attend.

While the Dr. Seuss Experience was most suited for families with young children, we absolutely loved our time at The Office Experience.

This indoor attraction is perfect for tweens, teens, and adults who love NBC’s The Office sitcom series.

Read all about our The Office Experience tour here, and find out what to expect when visiting there.

9. Visit the Lincoln Park Zoo

Lincoln Park Zoo is one of the oldest and largest free zoos in the country.

The zoo is open 365 days a year, which means that it’s even open in Chicago in the winter.

Lincoln Park Zoo has both indoor and outdoor exhibits that include big cats, polar bears, penguins, gorillas, reptiles, monkeys, and dozens of other species.

If you love animals, definitely consider the zoo in your list of winter activities in Chicago!

A perfect 3-day Chicago itinerary when visiting Chicago in winter, from top US family travel blog, Travel With A Plan!
The Museum of Science and Industry, Chicago

10. Go to a World-Class Museum

Chicago is home to a diverse array of museums that are a treasured part of the city’s cultural scene.

One of the best things to do in Chicago in winter in terms of indoor attractions is to one of its famous museums!

Our personal favorite museum in Chicago, especially if you’re visiting with tweens and teens, is the Museum of Science and Industry, Chicago.

This is by far the most enjoyable and innovative museum we have ever visited and its exhibits kept us entertained for hours in terms of all things Chicago.

Another museum hotspot is the Museum Campus located in the South Loop of Chicago.

The Museum Campus is home to 3 of the city’s leading institutions, all within walking distance of one another.

As a visitor to Chicago, you will be awed by any or all of these three magnificent museums:

  • Alder Planetarium (A museum dedicated to space and the study of astronomy.)
  • Shedd Aquarium (A gigantic aquarium featuring aquatic animals including beluga whales.)
  • Field Museum (A museum dedicated to natural history including fossils.)

Additional planning tip: Northerly Island Park is a 119-acre nature area and park on Chicago’s Museum Campus. Polar Adventure Days are held twice per winter and are a good outdoor activity to look into!

11. Attend Chicago’s Holiday Events

When it comes to Chicago winter activities, Chicago’s splendid holiday events simply have to make the list!

Even though events like the Christkindlmarket, holiday light displays, and live music are seasonal, it’s worth planning a trip to Chicago in December if you’re craving extra holiday spirit.

If you’re looking for things to do in December in Chicago, be sure to check the Choose Chicago website to see if Chicago’s holiday events match up with your visit during the holiday season.

Also, take your time while strolling on Magnificent Mile as there are dozens of opportunities to admire unique Christmas lights and Christmas decorations outside, and in the store windows.

12. Go to a Chicago Blackhawks Game

The Chicago Blackhawks is the local NHL hockey team that plays at Chicago’s United Center ice arena.

If you’re looking for things to do in the winter and you’ve never been to an NHL game, you’re missing out!

As one of the best things to do during winter in Chicago, get your and your group tickets to a Blackhawks game, dress up in the fan colors of red and black and get ready to have a blast cheering on the home team!

13. Stay at a Fun Downtown Hotel

There’s nothing better when traveling during the winter than to find a fantastic hotel that is as close to as many restaurants and attractions as possible (to cut down on driving and/or walking in the cold).

Here are some of our favorite family hotels in Chicago when spending 3 days in Chicago during the winter (or anytime, really!).

McCormick Tribune Ice Rink in Millennium Park

Winter in Chicago 3-Day Itinerary

Compressing your trip into a mere few days may feel like a challenge, but it’s possible to see the best of Chicago in winter in just three days.

Here’s exactly how we scheduled our 3-day Chicago itinerary in winter despite the Chicago snow and cold:

Day 1 in Chicago:

  • Check into the Embassy Suites Magnificent Mile
  • Walk to Navy Pier
  • Explore the pier, ride the Centennial Wheel and have a Chicago hot dog at American Dog & Burger
  • Walk, shop, and browse Magnificent Mile and have hot chocolate
  • Stop into Dylan’s Candy Shop
  • Go to a pop-up experience (we did the Dr. Seuss Experience and The Office Experience)
  • Take photos and explore the Chicago Riverwalk in winter; stop for hot chocolate at Ghirardelli Chocolate Shop in the Wrigley Building
  • Have dinner at Lou Malnati’s pizza at the Wrigley Building location on Michigan Avenue
  • Go swimming at the hotel

Day 2 in Chicago:

  • Go to the Museum of Science and Industry (We spent 3.5 hrs. there.)
  • Next, head to the Willis Tower
  • Have lunch within Catalog and then go to Skydeck
  • Walk around and take photos in Millenium Park/The Bean
  • Go ice skating at the Maggie Daley Ice Skating Ribbon
  • Walk across the street and have dinner at The Game Room in the Chicago Athletic Association Hotel
  • If you like sports and golf, rent the TopGolf Swing Suite at the Chicago Athletic Association for an hour or two

Day 3 in Chicago:

  • Have breakfast at Wildberry Pancakes and Cafe (one of our favorite family-friendly restaurants in Chicago!)
  • Spend the morning at Lincoln Park Zoo
  • Find your favorite spot to have an Italian Beef Sandwich for lunch
  • Go to the Shedd Aquarium (or to the museum of your choice)
  • Get dressed up and eat dinner out before going to a live Broadway show

If you’re a garden and landscape lover, another option is to visit the Chicago Botanic Garden or Garfield Park Conservatory which are both open year-round.

Though we did not get a chance to visit these places, this may be something you’re interested in.

Chicago in Winter Weather

In case you’re wondering, Chicago transforms into a winter wonderland during the months of December, January, and February. (Chicago in December weather is the most pleasant of the three.)

It doesn’t see as much snow as cities like Buffalo or Cleveland, but you’ll still be met with up to 10 inches of snowfall each year,

In addition to the snow, the Chicago winter weather is undeniably cold.

Visitors can expect to see Chicago winter temperatures with daily highs of 30 to 38°F, with lows plummeting to 22°F.

Be aware that the cold weather can vary massively across a single week though, so traveling and touring in layers is a must.

Lastly, you can expect to see some sun during your stay, but anyone visiting Chicago in winter should prepare for extensive cloud cover.

Overcast days are much more common than bright ones in these parts, so manage your expectations accordingly!

What to Pack for Chicago in Winter

Though it’s a beautiful city year-round, Chicago winter weather can catch you off guard if you don’t pack and prepare adequately.

We’ve already written a full guide on what to wear in Chicago (which you should check out!), but the biggest thing to remember when it comes to how to dress for Chicago winters is to be sure to account for the snow, cold, and blustering winds.

To make your adventure through Chicago in winter as seamless as possible, it’s a great idea to follow these travel tips and pack the following items:

  • Thermals (for both you and any kiddos) to protect from the wind chill
  • Plenty of long-sleeve shirts for layering
  • A selection of lightweight and heavier sweatshirts
  • Warm pants or thermal leggings
  • A reliable winter jacket or coat
  • A warm winter hat
  • Gloves (thermal if possible!)
  • A warm scarf
  • Snow boots or sturdy walking boots (rubber-soled options are excellent for handling Chicago’s perilous “black ice”)

It can be tempting to favor style over substance when you’re exploring any city, but you’ll be far more comfortable in Chicago winter weather if you stick to the basics and wrap up warm.

In terms of miscellaneous items, you may need the following:

  • Blankets for strollers
  • Hand warmers
  • A leak-proof thermos for morning coffee runs

*Read here if you’re interested in finding more Midwest winter weekend getaway ideas that are perfect for families!

*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*

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A perfect 3-day Chicago itinerary when visiting Chicago in winter, from top US family travel blog, Travel With A Plan!
A perfect 3-day Chicago itinerary when visiting Chicago in winter, from top US family travel blog, Travel With A Plan!
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Hi, I'm Jen - founder of the award-winning travel blog, Travel With A Plan! I help families plan fun & fulfilling family vacations by sharing our exact itineraries and "best things to do" lists to popular US vacation spots. Take the stress out of planning a family vacation by using our detailed destination guides and ultra-convenient packing lists to help you travel better. We'll show you how hassle-free family travel is possible - when you travel with a plan!

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