Things to Do in Chicago in Winter Worth Bundling Up For (Local Picks)

Updated: October 9, 2026

Chicago in winter isn’t just Christmas markets and twinkling lights, though I love those, too. There’s plenty to do after the holidays, from exploring museums and comedy shows to ice skating and warming up in a good cafe.

As a lifelong Chicago local, my favorite winter plans usually involve something interesting to see and somewhere delicious to eat afterward. The cold takes a little planning, but it doesn’t have to keep you from enjoying the city.

These are my recommendations for things to do in Chicago in winter, including indoor activities, outdoor experiences worth bundling up for, and Christmas events for anyone visiting during the holidays.

source: canva

This post contains affiliate links. I may receive a small commission for purchases made through these links at no extra cost to you. As an Amazon Associate, I earn from qualifying purchases. I personally use both Viator and GetYourGuide when booking travel experiences.

What to Expect from Chicago Winter Weather

Chicago winter weather can vary widely, from snowstorms to comfortable walking temperatures. Check the forecast close to your visit (7 days out or less for accuracy) and leave room to adjust your plans.

I recommend mixing indoor attractions with shorter outdoor stops. Spend an afternoon at a cool museum; we’ve got plenty, and many are near landmarks. Book a food/walking tour that combines outdoor stops with the Chicago Pedway (an underground network of tunnels). Just make sure to group nearby sights together so you’re not crossing the city every time you want to warm up.

How to Dress in Chicago in Winter

I see this question a lot. Honestly, bundle up. Better yet, layer up. Layers are your friend when you’re moving between cold streets and heated museums, shops, and restaurants.

Start with a warm coat, accessories and comfortable, waterproof shoes. For days with plenty of outdoor walking, I’d look for an insulated coat that helps block the wind. For winter trips, I always pack with these vacuum bags to keep bulky sweaters or layers from taking up too much space in my suitcase.

For a Chicago winter trip, I’d pack:

• An insulated coat with a hood and room for a sweater underneath
• Lots of sweaters 
• Base layers for colder days, like these thermal sets 
• Water-resistant or waterproof boots 
• The warmest socks you own, preferably thermal socks 
• A hat that covers your ears, thermal gloves, and a big ol’ scarf

source: canva

Things to Do in Chicago in Winter

When the weather outside is frightful, most visitors prefer indoor activities in Chicago. I’m listing some of those here, but don’t be afraid to venture outside. These activities include my favorite museums, comedy and magic shows, food tours, architecture, and skyline views, with suggestions to help you choose what’s worth your time.

Spend an Afternoon at a Chicago Museum

A museum is one of the easiest ways to enjoy Chicago when the weather makes outdoor activities less appealing. Choose one that interests you and give yourself enough time to explore, rather than rushing through several.

One of my favorites is the Griffin Museum of Science and Industry. During the holidays, its Christmas Around the World exhibit is an additional reason to visit; I cover that below in the Christmas section.

The Art Institute of Chicago is a great choice for art lovers, while the Field Museum offers another option for visitors interested in natural history. For a closer look at the city, consider another one of my faves: the Chicago History Museum.

If you like unique museums like me, don’t miss the Medieval Torture Museum, where you can learn about medieval torture practices and devices through interactive models. Another cool one is the International Museum of Surgical Science, showcasing the science and history of surgery & medicine. 

source: canva

Is a Chicago Attraction Pass Worth It?

A Chicago City Pass may be worth considering if you plan to visit several paid sights, such as museums and observation decks. Add up the individual tickets for the places you actually want to see, then compare that total with the current pass price and inclusions. Check reservation requirements and allow enough time at each attraction before deciding whether a pass fits your trip.

source: canva

Unique Chicago Tours, Shows, and Experiences

Beyond the museums and skyline views, Chicago offers plenty of winter experiences worth making time for. 

For an entertaining night out that doesn’t involve braving the cold, catch a comedy show at The Second City. This famous Chicago club is known for sketch comedy and improv, where stars like Tina Fey, Steve Carell, and Stephen Colbert got their start.

Or maybe add a little magic to your itinerary?✨

Chicago Magic Lounge is hidden behind a laundromat entrance in Andersonville; this speakeasy-style venue combines cocktails with table magic and stage performances. It’s a fun, unexpected night out, and I wholeheartedly recommend adding it to your winter plans. It’s one of our favorite things to do in the city! 

Here’s Jillian (from the popular Umbrella Vintage shop), the Jilly to my Lily, entering the magic lounge below.

Photo source: chicagomagiclounge.com

An interiors-focused architecture tour is also an excellent way to see Chicago beyond its skyline during the colder months. The Dazzling Interiors of the Loop tour explores beautiful building interiors with a guide, letting you see details you might otherwise miss up close. Check the current route before booking. Although the focus is on interiors, expect some outdoor walking between buildings.

If the cold doesn’t scare you (or the weather is mild) and you have limited time in the city, you can do a one-day tour of Chicago’s food, history, and architecture. It’s an excellent choice for first-time visitors.

Photo source: viator.com

See Chicago’s Skyline from an Observation Deck

An observation deck lets you enjoy sweeping views of Chicago without spending the afternoon outside. You don’t need to visit both; choose the one that appeals most, and check the visibility forecast before booking.

360 Observation Deck: Located on the 94th floor of the John Hancock building, it offers views of Chicago from every angle. If you only have time or money for one Chicago view, I vote for 360. I feel like it offers different lake views than the Skydeck.

Willis Tower Skydeck and The Ledge Ticket: The Skydeck inside the Willis Tower also offers incredible city views. I took the photo below from the Skydeck. Late afternoon is a great time to visit if you want to see the city in daylight and watch the lights come on. You can also step on “The Ledge” and see the city below you through a glass floor.

Try Chicago’s Food and Drink on a Guided Tour

A food tour is a fun way to try Chicago favorites while learning more about the city. For a winter visit, check how you’ll get between stops: some tours involve outdoor walking, while others include transportation.

Underground Donut Tour: No explanation needed. Do you love doughnuts? So do we. Visit four top Chicago shops and enjoy a variety of doughnuts at each. Plus, you’ll learn about the city’s food scene along the way. Two of the stops are Sawada and Do-Rite, which are two of my favorites. 

Chicago Pizza Tour: Enjoy a delicious pizza tour with bus transport included. Eat like a local and savor the best pizza as you travel into Chicago neighborhoods with an expert guide.

Chicago Favorites Ultimate Food and Walking Tour: Taste quintessential Chicago foods, including deep-dish pizza, hot dogs, famous popcorn and more. The cool thing about this tour is that in winter, they’ll take you through one of Chicago’s best-kept secrets: the Pedway. “This underground network of tunnels, bridges, and concourses weaves beneath the city’s central business district, connecting famous landmarks while keeping you cozy.”

Prefer to choose your own stops? I’ve shared my favorite places to eat in Chicago and my guide to Chicago cafes so that you can build a food-filled day around your other plans.

Source: facebook.com/doritedonuts

Warm Up in a Cozy Chicago Cafe

Not every winter activity needs a ticket. Sometimes the best break is a good latte and somewhere beautiful to sit after exploring the city. My favorite thing to do! 

I’d plan a cafe stop near the attractions you’re visiting rather than waiting until you’re freezing to find one. My Chicago cafe guide includes favorites around the city to help you choose. 

If you’re near the West Loop, try Discourse Coffee. It’s an incredible coffee experience. They call the cafe “a liquid workshop: an exploration of the art and craft of coffee.” If you’re in River North, Blue Bottle has a gorgeous cafe with city views.

If a gorgeous space matters more than the coffee, try Cafe Deko located in Printer’s Row in Chicago’s South Loop. We visited during Christmastime (photo below), and the shop was beautifully decorated. The coffee was so-so, but I loved the interiors.

Take a Chicago Architecture Boat Tour in Winter

A Chicago architecture river cruise can still be an option during a winter visit. Wendella offers year-round cruises with climate-controlled cabins, so you have a warm place to sit between times outside enjoying the skyline. 

I’ve taken a Wendella tour and have loved it. Winter hours are limited. Departures still depend on the schedule and conditions, so check availability before building your day around a boat ride. And dress warmly if you plan to spend time on the open deck.

First Lady’s season runs through late November. Shoreline Sightseeing is also showing bookings only through November. They both start back up the following year in mid-March to early April.

Read my detailed guide to help you choose the best Chicago architecture boat tour for your trip.

Go Ice Skating in Chicago

Ice skating is a classic winter activity in Chicago, and you don’t need to visit during Christmas to enjoy it.

The McCormick Tribune Ice Rink in Millennium Park offers a classic Chicago skating experience, with the Bean and downtown buildings as your backdrop. It’s a lovely way to spend a winter afternoon, especially if you follow it with a drink and a view at nearby Cindy’s Rooftop (they have firepits). Maggie Daley Park’s Skating Ribbon offers a different experience: instead of circling a traditional rink, you follow a winding path through the park with the skyline around you.

Another unique option is The Peninsula Sky Rink, located on the Peninsula Hotel terrace above Michigan Avenue. It’s a seasonal rooftop ice skating rink that typically runs from late November to mid-February. 

source: canva

Christmas Activities in Chicago

Visiting during the holidays? These Christmas activities add another layer to a Chicago winter trip. Many are limited to November and December, while some continue into early January, so check the dates before adding them to your plans.

You’ll find Christmas markets, light displays, and pop-up bars aplenty! I’m sharing my favorite yearly events along with other notable things to do.

Christkindlmarket in Chicago

I never miss the Christkindlmarket at Daley Plaza in downtown Chicago. You’ll feel like you’re wandering the streets of Europe, mulled wine in hand, as you shop for crafts and treats from local and European vendors. Admission is free. It usually runs from mid-November to Christmas Eve. 

Prefer to explore with a guide? A holiday food tour can combine seasonal sights with Chicago tastings. Check the current itinerary to see which market or light displays it visits and how much outdoor walking is involved.

Source: facebook.com/christkindlmarket

→ LondonHouse Chicago

For a central location with beautiful river views, I’d consider LondonHouse Chicago. It sits at Michigan Avenue and Wacker Drive, within walking distance of the Riverwalk, Magnificent Mile, Chicago Architecture Center, and Millennium Park. As mentioned, its rooftop offers my favorite view of the city. Its indoor bar, LH on 21, offers a place to enjoy a cocktail without braving the cold. Choose a river-view room if those iconic Chicago views are part of the appeal. Check rooms and rates at LondonHouse Chicago.

→ Waldorf Astoria Chicago

For a luxurious winter getaway, consider the Waldorf Astoria Chicago. It’s in the Gold Coast, within walking distance of Rush Street restaurants, Oak Street shopping, the Magnificent Mile, and 360 CHICAGO. The hotel’s spa and heated indoor lap pool make it especially attractive if you want to relax indoors for part of your trip. I’ve stayed here before and chose a room with a fireplace to defrost after my city walks. Check rooms and rates at Waldorf Astoria Chicago.

→ Chicago Athletic Association

For historic character and a convenient sightseeing base, I’d consider Chicago Athletic Association. It’s directly across from Millennium Park, with the Bean, McCormick Tribune Ice Rink, Art Institute, and Maggie Daley Park within walking distance. The Drawing Room’s fireplaces make it a particularly cozy winter choice, while Cindy’s offers beautiful views over the park. Check rooms and rates at Chicago Athletic Association.

Chicago in winter is easier to enjoy when you leave room for the weather. Choose a few things you’re excited to see, plan somewhere good to warm up afterward, and keep your outdoor stops flexible.

The summer crowds are gone, the streets are sparkling, and the restaurants are dressed to the nines. I’d say it’s one of the best times to visit.