Embracing Winter in Chicago: Best Things to Do
I’m no great fan of the cold weather, but every year I’m trying to embrace the Chicago winter season with open arms. I start out fine, kicking it off in late November with the Lights Festival parade down Michigan Avenue, and then onto Christmas when the city comes alive with holiday decor. I’m even okay a few weeks into January, when the holiday lights are still ablaze, giving off a feeling of warmth. That’s about the time I start looking for ways to really enjoy everything Chicago has to offer in the winter.
While the temperatures may drop, the city’s energy remains vibrant, offering a plethora of activities that make the chilly months enjoyable. Here are my top ten recommendations to experience the best of Chicago during winter:
Soak in Panoramic Views from 360 CHICAGO Observation Deck
Address: 875 N. Michigan Ave., Chicago, IL 60611
For breathtaking vistas, the 360 CHICAGO Observation Deck atop the John Hancock Center is unparalleled. The TILT experience provides an exhilarating adventure, allowing you to lean out over the city from 1,030 feet above the Magnificent Mile. On clear winter days, the visibility stretches for miles, offering a unique perspective of the snow-covered cityscape. My first visit to 360 Chicago was in January, and I’ll admit I was a bit nervous. I’m no hero when it comes to heights, but once I summoned to courage to step out onto the obervation deck and grasp the side rails as I was slowly tilted over the city, I was filled with exhilaration. Let me put it this way: if I can do it, you can, too!
- Admission: General Admission starts at $30 for adults; TILT experience available for an additional fee
Glide Through Maggie Daley Park’s Skating Ribbon
Address: 337 E. Randolph St., Chicago, IL 60601
One of my favorite winter traditions is lacing up my skates and taking a spin on the Maggie Daley Park Ice Skating Ribbon. Unlike traditional rinks, this quarter-mile ribbon winds through the park’s landscape, offering scenic views of the city skyline. Whether you’re a seasoned skater or a beginner, the ribbon accommodates all skill levels. Remember to reserve your spot in advance, especially on weekends.
- Admission:
- Monday–Thursday: With Skate Rental: $17 online + tax; Bring Your Own Skates: Free (excluding holidays)
- Friday–Sunday and Holidays: With Skate Rental: $21 online + tax; Bring Your Own Skates: Free at 11am session; $5 + tax for 2pm, 5pm & 8pm sessions
EXPERT TIP: My favorite time to skate at Maggie Daley is during the week when the sun is shining and the sky is blue. I’ll take the afternoon off and head for the rink for little peace and quiet in the iddle of the city. It’s pure Chicago winter bliss.
Cozy Dining in Winter Igloos at LondonHouse Chicago
Address: 85 E Wacker Dr, Chicago, IL 60601
For a unique dining experience with stunning panoramic views, I recommend reserving one of the winter igloos at LondonHouse Chicago’s LH Rooftop. These heated igloos provide a cozy retreat high above the city, perfect for the Chicago River, Magnificent Mile, and the glittering skyline. Whether you’re celebrating a special occasion or just looking for a unique way to enjoy a winter evening, these igloos offer a warm and intimate setting unlike anywhere else in the city.
Each igloo is available by reservation and includes a curated menu of handcrafted cocktails, small plates, and decadent desserts, making it an ideal spot to unwind after a chilly day exploring Chicago. The festive atmosphere, complete with twinkling lights and plush seating, creates the perfect winter escape without having to brave the cold. Since availability is limited and these igloos are incredibly popular, I recommend booking your reservation well in advance, especially if you’re planning a visit on a weekend or around the holidays.
- Reservations: Required
EXPERT TIP: If you’re looking for a cozy, unforgettable winter dining experience with some of the best views in the city, this is the spot to be!
Warm Up at the Garfield Park Conservatory
Address: 300 N. Central Park Ave., Chicago, IL 60624
When winter’s chill becomes too much, a visit to the Garfield Park Conservatory feels like a tropical escape. This lush sanctuary houses thousands of plant species across various climates, from arid deserts to dense rainforests. It’s the perfect spot to shed your coat and bask in warmth while surrounded by vibrant greenery.
- Admission: Free for Chicago residents and members; admission fees apply for non-residents
Step Back in Time at the Chicago History Museum
Address: 1601 N Clark St, Chicago, IL 60614
For a fascinating dive into Chicago’s past, spend an afternoon exploring the Chicago History Museum in Lincoln Park. Winter is the perfect time to discover this treasure trove of exhibits that chronicle the city’s rich history, from its Great Fire of 1871 to its influence on music, culture, and politics.
One of my favorite exhibits is “Chicago: Crossroads of America,” which walks you through the city’s transformation from a small trading post to a global metropolis. Another must-see is the “Facing Freedom in America” exhibit, which examines civil rights movements and the ongoing fight for justice and equality. If you’re a fashion enthusiast, you’ll love the “Silver Screen to Mainstream” exhibit, showcasing how Hollywood glamor influenced everyday Chicago fashion from the 1930s to the 1950s.
The museum is also home to Abraham Lincoln artifacts, including the very bed he died in after his assassination. And if you’re visiting with kids, don’t miss The Great Chicago Adventure, an immersive multimedia experience that brings the city’s history to life.
- Admission: Adults: $19; Seniors (65+), Students (13–22): $17
EXPERT TIP: Before you leave, step outside and take a winter stroll through Lincoln Park, where you can admire historic statues, snow-covered trails, and stunning views of the skyline.
Indulge in Italian Delights at Eataly Chicago
Address: 43 E. Ohio St., Chicago, IL 60611
For a culinary adventure, Eataly Chicago in River North is a must-visit. I often spend hours wandering through the marketplace, sampling artisanal cheeses, fresh pastas, and delectable pastries. After shopping, I treat myself to a glass of wine at their cozy wine bar, followed by a sumptuous meal at one of their in-house restaurants. It’s a delightful way to experience a slice of Italy without leaving the city.
- Admission: Free to enter; prices vary by product and restaurant
Engage with Nature at the Peggy Notebaert Nature Museum
Address: 2430 N. Cannon Dr., Chicago, IL 60614
If you have children, the Peggy Notebaert Nature Museum is a fantastic destination. In fact, my now-grown kids rank the Peggy Notebaert right up there with the Lincoln Park Zoo in their favorite childhood haunts. My kids always delighted in the Butterfly Haven, where hundreds of butterflies flutter freely in a tropical environment. The interactive exhibits make learning about ecosystems and conservation both fun and educational.
- Admission: $9 for adults; discounts available for students, seniors, and children
Experience Gilded Age Splendor at the Driehaus Museum
Address: 50 E. Erie St., Chicago, IL 60611
Stepping into the Driehaus Museum is like traveling back to Chicago’s Gilded Age. Housed in the meticulously restored Nickerson Mansion, the museum showcases stunning architecture and a rich collection of decorative arts. I love wandering through its opulent rooms, each telling a story of the city’s lavish past.
- Admission: Adults $20; Seniors (65+) $15; Students with ID $10; Children 12 and under free
Explore the Wonders of Museum Campus
Chicago’s Museum Campus is a treasure trove of knowledge and adventure. On those particularly frosty days, I love immersing myself in the exhibits at the Field Museum, marveling at the aquatic life in the Shedd Aquarium, or exploring the cosmos at the Adler Planetarium. Each institution offers unique experiences that captivate visitors of all ages.
Field Museum
- Address: 1400 S. DuSable Lake Shore Dr., Chicago, IL 60605
- Admission: General Admission starts at $25 for adults; discounts available for Chicago resident
Shedd Aquarium
- Address: 1200 S. DuSable Lake Shore Dr., Chicago, IL 60605
- Chicago residents: $19.95 adult general admission; prices vary for non-residents and special exhibits
Adler Planetarium
- Address: 1300 S. DuSable Lake Shore Dr., Chicago, IL 60605
- Admission: General Admission starts at $19 for adults; discounts available for Chicago residents
Stroll Along Montrose Beach
Address: 4400 N. Lake Shore Dr., Chicago, IL 60640
While Lake Michigan’s beaches are summer hotspots, there’s a serene beauty to them in winter. Bundling up and taking a walk along Montrose Beach offers peaceful views of the icy shoreline and the city beyond. It’s a tranquil retreat from the urban hustle, and if you’re lucky, you might spot some wintering birds along the way.
There’s a dog beach, too, so I always bring our pup along to run free and enjoy some wintery breezes off of Lake Michigan.
- Admission: Free
Embrace Chicago’s Winter Magic
Winter in Chicago is full of adventure, whether you’re gliding across an ice ribbon, warming up in a tropical conservatory, admiring breathtaking city views, or indulging in cozy, one-of-a-kind dining experiences. While the cold may be brisk, the city’s energy never fades, offering plenty of ways to explore, experience, and enjoy the season.
Which of these winter activities is your favorite? Drop a comment below and let me know!