Chicago, the city of rom coms, deep dish pizza, and infamous wind, may seem like a surprising winter destination, but beauty and tranquility hide just under the surface. My daughter and I recently returned from a girl’s trip to Chicago — America’s idyllic winter wonderland.
Here are our top 10 favorite things to do in Chicago this winter. From cozy cafés to art galleries and breathtaking Christkindlmarkets, get ready to discover a whole new side of Chicago that will leave you mesmerized.
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The Rookery
This historic building, completed in 1888, is located in the Loop neighborhood, a must-see for any architecture enthusiast. It showcases a unique blend of architectural styles, including Romanesque Revival and Chicago School architecture.
Frank Lloyd Wright redesigned the lobby in 1905. His light-filled atrium features a beautiful ironwork staircase and glass ceiling, creating an enchanting ambiance. It earned its name due to the pigeons that used to nest in its rooftop, resembling a rookery. Over the years, it has been home to various businesses and played a significant role in Chicago’s commercial and cultural scene.
Today, the Rookery Building is a thriving office building. While visitors are welcome to explore the first floor of the atrium for free, it is also possible to take a tour through the Frank Lloyd Wright Trust.
Harold Washington Library
The Harold Washington Library is an impressive 10-story building that blends modern and classical architectural elements. Its grand neoclassical exterior and beautifully detailed façade make it a striking presence in the city skyline.
The library holds a large collection of materials making it a haven for bookworms. On the 8th floor you can see Cloud Gate maquette, or a tiny bean! The atrium has a multi-story glass ceiling allowing natural light to flood in, creating a bright and inspiring space. I was excited to see the Winter Garden, located on the top floor, that offers panoramic views of the city. However, it was closed for renovations during our visit.T
Chicago Cultural Center
Located in the historic former Chicago Public Library building, the Cultural Center is known for its breathtaking domes: the Tiffany stained-glass dome and the smaller, more somber GAR dome. A wide range of attractions will captivate your imagination here, like the rotating art exhibitions featuring local and international artists. The center offers free admission to all exhibitions and events, making it an welcoming public space.
The Art Institute of Chicago
Explore one of the oldest and largest art museums in the country, housing a remarkable collection of masterpieces. Since my first visit many years ago, this museum has been one of my favorite art museums in the world. At the Art Institute, you’ll have the opportunity to admire masterpieces like Vincent van Gogh’s Bedroom, Pablo Picasso’s Old Guitarist, Claude Monet’s Waterlilies, Grant Wood’s American Gothic, and Georgia O’Keeffe’s Sky Above Clouds. The museum’s collection includes a wide range of mediums, including paintings, sculptures, photography, and textiles.
Chicago Athletic Association
This historic landmark, recently turned luxury hotel, is a hub of history, leisure, dining, and architecture. It is a gathering place for locals and travelers located in the heart of Chicago near Millennium Park and the Art Institute. For over a century, this club was reserved for the elite, but today anyone is welcome. The interior reminds me of an Ivy League library!
Upon entering the building, you will notice Shake Shack on your left and Fairgrounds Chicago, a busy coffee shop to your right. Order a coffee and continue up the marble stairs to the Drawing Room. This hygge space is full of cozy seating, lush greenery, and warm ambiance. The space offers a quiet refuge from the busy Chicago streets below, and encourages meaningful conversations, uninterrupted work, and time to relax. The Drawing Room feels like a step back in time to when Hemingway was writing and movie stars were socializing. Consider having a bit to eat at one of the many bars and restaurants inside the Chicago Athletic Association, including Cindy’s Rooftop and the Game Room.
The Magnificent Mile
Take a leisurely stroll along the iconic Magnificent Mile, marvel at iconic buildings adorned in elaborate holiday lights and festive window displays. We enjoy simply window shopping, and often stop at the Reserve to warm up with a hazelnut Bianco latte from the world’s largest Starbucks.
Shop Under the Mistletoe
Chicago’s German-style Christkindlmarket is so popular that it has spread to multiple locations today. We visited the Daley Plaza Christmas Market under the famous 1963 Picasso sculpture. We spent over an hour wandering through the maze of stalls with twinkling lights, handcrafted German gifts, and live music. While shopping for unique gifts for friends and family, we stopped for sweet and savory treats like roasted nuts, fresh pretzels, bratwurst, hot chocolate and hot spiced wine in souvenir mugs.
Enjoy a meal at 3 Arts Club Cafe
One of the most memorable experiences of our trip was enjoying a meal in RH’s 3 Arts Club Cafe. Although reservations book well in advance, we were fortunate to stop in early and have the opportunity to enjoy a delicious Saturday morning brunch without one!
Three Arts Club, built in 1914, served as a residence for young women studying music, drama and the visual arts. Today RH has reimagined the space, to match their “vision to create architecturally inspiring and immersive spaces that blur the lines between residential and retail, indoors and outdoors, home and hospitality.” This space is arguably still a haven for artists including culinary arts, interior design, and architecture. This six floor retail space welcomes one to pause and dream about the possibilities in life.
Lincoln Park's Zoo and Conservatory
After our delicious brunch, we headed nearby to Lincoln Park. We chose to only explore the botanical garden due to rain. The conservatory is a tranquil escape from the bustling city. The conservatory is divided into different rooms, each representing a unique ecosystem. In addition to the main Victorian-era greenhouse, you can also enjoy the palm house, fern room, and orchid room. Note that free online reservations are required.
See a Classic Show
While Chicago is home to the symbolic theater, built in 1921, there are shows in theaters throughout the city creating a delightful variety to choose among. Check out what is available, and prepare to cozy up in a velvet-plush theater seat for a timeless holiday show. We chose “It’s a Wonderful Life” playing in a small theater north of downtown. We enjoyed the 1940’s style radio show and the audience was invited to enjoy eggnog and homemade cookies with the actors after the show. In my opinion, it was a wonderful way to prepare for the holiday season.
This is just a taste of the magic that awaits in Chicago’s winter wonderland. So, grab your mittens, your holiday spirit, and get ready for an unforgettable winter adventure in the Windy City! Don’t forget to check out local events and festivals for unique experiences. Share your favorite winter finds in the comments below!
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