Chicago in December - Things to Do & What to Wear

Chicago in December – Things to Do & What to Wear

Winter in Chicago is a magical time of the year, with snow-covered streets and plenty of festive activities to enjoy. From ice skating at Millennium Park to sledding at Soldier Field, there are numerous outdoor activities to keep you entertained. If you prefer indoor attractions, the city is home to world-class museums and theaters. When it comes to fashion, it’s important to dress warmly with a winter coat, gloves, hat, and boots to stay comfortable in the cold temperatures.

Key Takeaways:

  • Chicago in December offers a range of outdoor and indoor activities for visitors.
  • Outdoor activities include ice skating, sledding, and snowshoeing.
  • Indoor activities include visiting museums, watching shows, and exploring indoor gardens.
  • Don’t miss the chance to experience the unique rooftop bars and restaurants in Chicago.
  • Dress warmly with a winter coat, gloves, hat, and boots to stay comfortable during your visit.

Outdoor Activities in Chicago in December

During December in Chicago, there are numerous outdoor activities to enjoy, making the most of the winter season. Whether you’re a fan of ice skating, sledding, snowshoeing, or simply admiring the frozen landscapes, the city offers a wide range of options for outdoor enthusiasts.

Ice Skating

One of the quintessential winter activities in Chicago is ice skating. The city boasts several outdoor ice rinks where you can glide across the ice and enjoy breathtaking views of the city skyline. Popular locations include:

  • Millennium Park ice rink
  • Skating Ribbon at Maggie Daley Park
  • Midway Plaisance Ice Rink on the University of Chicago campus
  • Sky Rink at the Peninsula Chicago

Whether you’re a seasoned skater or a beginner, these ice rinks provide a magical atmosphere for all ages to enjoy.

Sledding and Snowshoeing

If you’re seeking a thrill, head to the Soldier Field sledding hill, where you can slide down the slopes and feel the rush of adrenaline. Alternatively, if you prefer a more serene outdoor experience, consider snowshoeing on Northerly Island. Explore the winter wonderland and immerse yourself in the tranquil beauty of nature.

Frozen Lake Michigan

No visit to Chicago in December is complete without admiring the frozen Lake Michigan. As the city’s iconic backdrop, the frozen lake offers stunning views of the city skyline and creates a surreal landscape. Take a leisurely stroll along the lakefront or capture memorable photos against this picturesque backdrop.

Winter Rooftop Activities

For a unique experience, consider exploring the winter rooftop activities that Chicago has to offer. From rooftop bars with heated enclosures to restaurants with cozy outdoor seating, there are plenty of options to enjoy the city’s skyline while staying warm. Indulge in a delightful meal, sip on a hot drink, and take in the breathtaking views of Chicago’s winter beauty.

Experience the best of Chicago’s outdoor activities in December and embrace the magic of the winter season. Whether you choose to skate, sled, snowshoe, or simply admire the frozen landscapes, there’s something for everyone to enjoy.

Indoor Activities in Chicago in December

If you prefer to stay indoors during your visit to Chicago in December, there are plenty of options for entertainment. The city is home to world-class museums such as the Field Museum, the Art Institute of Chicago, and the Museum of Science and Industry. You can also catch a show at one of the many theaters in the downtown theater district or explore the interactive Museum Campus South. For a family-friendly activity, visit the Lincoln Park Zoo, which is open year-round. Additionally, Chicago has several indoor gardens and conservatories where you can escape the cold and enjoy the beauty of nature. Don’t forget to warm up with a cup of hot cocoa at one of the city’s top spots for this winter treat.

Museums in Chicago

If you’re a fan of art, history, or science, Chicago’s museums offer a wealth of knowledge and cultural experiences. From ancient artifacts to modern masterpieces, you’ll find it all in these remarkable institutions:

  • Field Museum: Discover the wonders of natural history through captivating exhibits and interactive displays.
  • Art Institute of Chicago: Immerse yourself in a world of art, featuring renowned works from artists around the globe.
  • Museum of Science and Industry: Engage with hands-on exhibits that explore the frontiers of science and technology.

Shows in Chicago

Chicago’s vibrant theater scene offers something for everyone, from Broadway productions to local performances. Don’t miss the chance to catch a show and immerse yourself in the world of live entertainment:

  • Theater District: Explore the bustling downtown district and choose from a variety of theaters showcasing plays, musicals, and more.

Lincoln Park Zoo

Spend a day at the Lincoln Park Zoo, located in the heart of Chicago. This free attraction is open year-round and offers a chance to see a wide array of animals up close. From playful penguins to majestic lions, the zoo provides a memorable experience for visitors of all ages.

Indoor Gardens in Chicago

Escape the winter chill and step into a world of lush greenery and blooming flowers at Chicago’s indoor gardens and conservatories. Experience the beauty of nature in these tranquil settings:

  • Garfield Park Conservatory: Explore this botanical wonderland spanning over 12 acres, featuring vibrant plant displays and scenic landscapes.
  • Chicago Botanic Garden: Discover the beauty of nature through themed gardens, including the serene Japanese Garden and the colorful English Walled Garden.

Hot Cocoa in Chicago

Warm up with a delicious cup of hot cocoa at one of Chicago’s cozy cafés and bakeries. Indulge in this seasonal favorite and treat yourself to a sweet and comforting experience. Here are some popular spots to satisfy your cocoa cravings:

  • Beatrix: Enjoy a flavorful cup of hot cocoa with a twist, infused with flavors like salted caramel or Mexican hot chocolate.
  • Mindy’s Hot Chocolate: Experience indulgence at its finest with Mindy Segal’s renowned, rich hot chocolate creations.
  • World of Chocolate Museum and Café: Discover the artistry of chocolate while sipping on a steaming cup of hot cocoa in this unique museum café.

Rooftop Bars and Restaurants in Chicago in December

Despite the cold temperatures, Chicago offers a vibrant rooftop dining scene even in December. Experience the city’s breathtaking winter views while enjoying delicious food and drinks at these popular rooftop bars and restaurants.

Cindy’s Rooftop

Cindy’s Rooftop, located at the Chicago Athletic Association Hotel, is a must-visit spot for rooftop dining. Situated in the heart of the city, this chic rooftop bar offers panoramic views of the Chicago skyline. Indulge in their delicious menu featuring a variety of dishes showcasing local flavors, and sip on craft cocktails while taking in the winter beauty of the city. With its cozy atmosphere and stunning views, Cindy’s Rooftop is the perfect place for a memorable dining experience.

The Robey’s Up Room

Another fantastic rooftop option is The Robey’s Up Room. Located in the trendy Wicker Park neighborhood, this stylish rooftop bar offers unobstructed views of the Chicago skyline. Enjoy their carefully curated menu that features a mix of international flavors and creative cocktails. Whether you’re there for a romantic dinner or a casual gathering with friends, The Robey’s Up Room guarantees a unique and memorable dining experience.

If you prefer a more traditional bar setting, Chicago also boasts several cozy bars where you can escape the cold and unwind with a warm drink.

Cozy Bars in Chicago

Bar Location Atmosphere
The Violet Hour 1520 N Damen Ave Intimate and speakeasy-inspired
The Berkshire Room 15 E Ohio St Classic cocktail lounge with a cozy ambiance
The Whistler 2421 N Milwaukee Ave Artistic setting with live music performances

These cozy bars offer a warm and inviting atmosphere, perfect for enjoying winter nights in Chicago. Whether you’re looking for a quiet evening or a lively gathering, the city has a rooftop or cozy bar to suit your taste.

Enjoy the stunning winter views of the Chicago skyline while sipping on a cocktail or indulging in a delicious meal. Whether you choose a rooftop bar or a cozy bar, these Chicago establishments provide a unique and memorable dining experience during the colder months.

What to Wear in Chicago in December

When visiting Chicago in December, it’s important to dress appropriately for the cold weather. The Windy City can experience freezing temperatures and heavy snowfall during this time of year, so it’s essential to stay warm and cozy. Here are some key items to include in your winter wardrobe:

  • Winter coat: Invest in a high-quality, insulated winter coat to protect yourself from the chilly winds. Opt for a waterproof option to stay dry in case of snowfall.
  • Gloves: Don’t forget to bring a pair of warm gloves to keep your hands protected from the cold. Look for gloves with insulation or thermal lining for added warmth.
  • Hat: A hat is essential to keep your head warm and prevent heat loss. Choose a beanie, knitted hat, or a stylish woolen cap to add a touch of winter fashion to your outfit.
  • Boots: Invest in a sturdy pair of waterproof boots with good traction to navigate through the snowy streets of Chicago. Look for insulated boots that provide both warmth and protection.
  • Thick socks: Layering is key to staying warm, even for your feet. Wear thick, thermal socks to keep your toes cozy throughout the day.
  • Scarves: A scarf not only adds an extra layer of warmth but also adds style to your winter outfit. Choose a cozy, chunky knit scarf or a fashionable plaid pattern to stay on-trend.

Remember, layering is key to staying comfortable in the fluctuating temperatures of Chicago in December. Consider wearing thermals or long-sleeved base layers under your clothing for added warmth. Pair your winter essentials with sweaters, long pants, and other winter-friendly garments to stay cozy and stylish.

Embrace the winter fashion in Chicago by blending warmth and style. Choose a fashionable winter outfit that reflects your personal taste and showcases your unique sense of style. Don’t be afraid to experiment with different fabrics, textures, and colors to create a chic winter look.

With the right wardrobe essentials and a touch of personal style, you’ll be ready to explore all that Chicago has to offer in December, from outdoor activities to indoor attractions.


Chicago in December is a haven for winter enthusiasts, offering a plethora of activities and experiences that cater to all interests. Whether you’re a fan of outdoor adventures or prefer to explore indoor attractions, the Windy City has something for everyone.

For those seeking outdoor thrills, ice skating and sledding at popular spots like Millennium Park and Soldier Field bring joy and excitement. The glistening frozen Lake Michigan also provides a mesmerizing backdrop for winter walks or snowshoeing.

If you’d rather stay cozy indoors, Chicago’s world-class museums and theaters dazzle visitors with their cultural offerings. The Field Museum, the Art Institute of Chicago, and the Museum of Science and Industry are just a few of the remarkable institutions waiting to be explored. You can also immerse yourself in nature at the city’s indoor gardens and conservatories, or enjoy a heartwarming cup of hot cocoa at one of Chicago’s top spots.

To make the most of your visit, don’t forget to bundle up in warm winter attire. Embrace the city’s winter fashion scene with a stylish coat, gloves, hat, and boots to brave the chilly temperatures. By following this Chicago winter travel guide, you’ll ensure a memorable experience in the beautiful and enchanting city of Chicago in December.


What are some outdoor activities to do in Chicago in December?

Some popular outdoor activities in Chicago in December include ice skating at Millennium Park, sledding at Soldier Field, snowshoeing on Northerly Island, and admiring the frozen Lake Michigan.

What are some indoor activities to do in Chicago in December?

Chicago offers a variety of indoor activities in December, including visiting world-class museums like the Field Museum and the Art Institute of Chicago, catching a show at one of the downtown theaters, exploring the interactive Museum Campus South, and visiting the year-round open Lincoln Park Zoo.

Are rooftop bars and restaurants open in Chicago in December?

Yes, many rooftop bars and restaurants in Chicago remain open in December, offering unique and cozy dining experiences with stunning views of the city skyline.

What should I wear in Chicago in December?

It’s important to dress warmly in Chicago’s cold December weather. Wear a warm winter coat, gloves, hat, and boots. Layering with thermals, long pants, sweaters, and thick socks will help keep you warm. Don’t forget to pack a scarf and a fashionable winter outfit to embrace the city’s winter fashion scene.

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