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Must-Do Chicago January Events: An Enchanting Winter Experience

Updated: Apr 15

For those looking for a culinary adventure, don't miss the Chicago Restaurant Week where you can taste dishes from the city's top chefs at discounted prices. If you're into music, the Tomorrow Never Knows festival is a must-visit, featuring indie rock, pop, and hip hop artists. For a more active experience, the city's parks offer ice skating, and the Polar Bear Plunge is a unique (and chilly) way to give back to the community. Lastly, don't forget to check out the city's iconic museums, many of which offer free admission on select days in January.

Lightscape at Chicago Botanic Garden

Lightscape at the Chicago Botanic Garden is an enchanting winter event that features a trail illuminated with stunning light displays. This immersive experience allows visitors to wander through a magical landscape lit with thousands of lights, creating a captivating spectacle. The displays often include interactive elements, and the event is accompanied by festive music, making it a delightful sensory experience. It's a fantastic family-friendly activity and a unique way to enjoy the beauty of the garden at night in the winter season.

Chicago International Puppet Festival

JANUARY 18-28, 2024

The International Puppet Festival in Chicago is an event that showcases puppet artists from around the world. This festival is a significant part of the city's vibrant arts scene and is known for its diverse and innovative performances. Puppets of all shapes and sizes, from traditional hand puppets to complex marionettes, take the stage to tell stories that captivate audiences of all ages. The festival typically includes performances by both local and international puppeteers, offering a chance to see a wide range of puppetry styles and techniques. It's an event that celebrates the art of puppetry and its power to inspire, challenge, and entertain.

Illumination: Tree Lights at the Morton Arboretum


"Illumination: Tree Lights at the Morton Arboretum" is a popular winter event that transforms the Morton Arboretum into an enchanted forest lit up with interactive light displays. This mesmerizing spectacle features artistic installations and colorful lighting effects that highlight the natural beauty of the trees in the arboretum. It's an immersive experience that combines art and nature in a magical winter setting, making it a must-see event for families, couples, and anyone looking to experience a unique outdoor light exhibition. The event also often includes a variety of festive activities and delicious seasonal treats for visitors to enjoy.

Winterland at Gallagher Way


Light up "Winterland" letters in Christmas decoration
Wrigleyville Winterland inside Wrigley Field

Winterland at Gallagher Way is an annual event that typically includes a variety of winter-themed activities. It often features an ice skating rink, holiday decorations, and opportunities to meet Santa. There is also be special events, such as movie nights and crafting sessions. Vendors usually sell food, drinks, and holiday gifts on the outside as part of the Christkindlmarket. The event aims to provide a festive community space where locals and visitors can enjoy the holiday season.

See live theatre

Chicago boasts a vibrant theatre scene, with numerous performances taking place throughout the city. From large, Broadway-style productions to smaller, independent plays, there's a wide range of theatrical experiences to enjoy. In January 2024, there are several notable live theatre performances taking place.

One significant event is "The Infinite Wrench," a show that blends performance, storytelling, and a touch of comedy. It's an

Light up Chicago Theatre Marquee at night
Chicago Theatre Marquee Sign

ongoing, ever-changing attempt to perform 30 plays in 60 minutes. You can catch this unique and dynamic performance on January 5th, 2024.

Hamilton The Musical is a stunning performance you simply cannot miss. Beautifully written and composed.

Beautiful: The Carol King Musical is a touching tribute to the legendary singer-songwriter that will tug at your heartstrings.

Illinoise is a captivating narrative that will be running from January 28 to February 19.

Cinderella, the classic fairy tale brought to life on stage, will be enchanting audiences until January 7.

Dial M for Murder, a gripping drama filled with suspense, will keep you on the edge of your seat until January 7.

Fiddler on the Roof, a timeless tale of family and tradition, will be running from January 24 to March 17.

Dog Man The Musical is a hilarious adaptation of the popular children's book series.

Drunk Shakespeare is a unique and entertaining twist on the classic works of the Bard.

Blue Man Group, a performance art company known for their innovative and electrifying shows, is a must-see.

Fillet of Solo Festival

JANUARY 12TH-21ST, 2024

The Fillet of Solo Festival is a celebration of storytelling and solo performance. This event showcases talented storytellers and performers from around the city and beyond. It's the perfect opportunity to experience a diverse range of voices and stories in a unique, intimate setting. Each performance is a unique blend of personal narrative and creative expression, making for a memorable and inspiring experience.

Chicago Restaurant week


Chicago Restaurant Week 2024 is a culinary event where you can taste dishes from the city's top chefs at discounted prices. It's an excellent opportunity to explore the rich culinary scene of Chicago, sampling a variety of cuisines and dishes. Whether you're a foodie or just enjoy trying new foods, it's an event not to be missed.

Eataly Made in Italy Taste-Around

Eataly's Made in Italy Taste-Around in Chicago is a culinary event where you can explore and savor a variety of Italian flavors. This event showcases a multitude of dishes and products, all made with authentic Italian ingredients. It's an excellent opportunity to discover Italy's rich culinary tradition and its regional delicacies. The event typically includes tastings of a variety of foods and drinks, from cheeses and cured meats to wines and desserts. It's an immersive gastronomic experience that transports you to Italy without leaving Chicago.

Handmade Market


The Handmade Market in Chicago is a unique event that takes place in January. It is a gathering of local artisans and crafters showcasing their handmade items, which may include jewelry, clothing, home decor, and other unique and creative pieces. This market provides an excellent opportunity to support local businesses, find one-of-a-kind items, and discover new artists and crafters. It is a fantastic place to find unique gifts or to treat yourself to something special. The Handmade Market offers a warm and vibrant atmosphere that highlights the creativity and talent within the Chicago community.

Brewery Tours

Hopewell Brewery Canned Beer
Dram Hopewell Beer Tasting

Taking a brewery tour in Chicago in January is a great way to spend a winter day. Indoors, away from the chill, you'll have the opportunity to learn about the city's rich brewing history, see how beer is made, and, of course, sample some unique local brews. It's a chance to explore Chicago's vibrant craft beer scene, which includes a diverse range of breweries each with their own unique styles and flavors. The tours are also often led by knowledgeable guides, making it an educational experience as well. Plus, it's a fun group activity, perfect for both locals and visitors alike.

Check out these Brewery Tours

Rooftop Snowglobes

Rooftop snowglobes in Chicago provide a unique and cozy way to enjoy the city's winter atmosphere. They offer a panoramic view of the city's stunning skyline while protecting you from the harsh winter elements. It's a great place for socializing, dining, or simply enjoying a warm drink amidst the chill. These snowglobes often feature heaters and comfortable seating, providing a unique and memorable winter experience.

Check out these rooftop locations:

  • Village Tap

  • Cafe Ba Ba Reeba

  • The Boiler Room

  • Off Site Bar

  • Irazu

  • Alma

  • The Godfrey Hotel

Check out some Museums

Woman standing in a blue room surrounded by stars
Adler Planetarium
Long vertical skylight in the Chicago Institute of Art
Chicago Institute of Art
January is an excellent time for locals to visit museums in Chicago because it's a quieter time of year when tourist crowds are typically smaller. This allows for a more relaxed and personal experience. Additionally, many museums offer free admission on select days in January, making it an affordable cultural outing. It's also a great indoor activity to escape the chill of the Chicago winter.

Watch the Chicago Bulls Play

Stands view of Chicago Bulls Basketball game
Bulls Game at United Center

Watching the Chicago Bulls play in January is an exhilarating experience as it's in the heart of the NBA season, with teams in full swing. Attending a game not only offers the thrill of live basketball at its highest level but also an exciting atmosphere with loyal fans. If you're a sports fan, it's a great opportunity to see top-tier athletes in action. Even if you're not, the energy, entertainment, and community feel make it a memorable event. Plus, you'll get to be a part of Chicago's rich sports culture.

Upcoming Games

  • Jan 5th V Charlotte Hornets

  • Jan 10th Houston Rockets

  • Jan 12th Golden State

  • Jan 20th Memphis Grizzlies

  • Jan 30 Toronto Raptors

Tomorrow Never Knows

Tomorrow Never Knows is a diverse music festival in Chicago that takes place every January. The festival features a mix of indie rock, pop, and hip hop artists, showcasing both local talent and internationally recognized performers. It's known for its intimate venues and eclectic lineups, making it an ideal event for music lovers looking to discover new artists or see their favorites in a more intimate setting. Whether you're a Chicago resident or a visitor, Tomorrow Never Knows offers a unique, immersive music experience to kick off the new year.

Run (or support) MLK Jr Day Freedom Run Chicago

The MLK Jr Day Freedom Run is an annual event in Chicago that takes place on Martin Luther King Jr. Day. This run is a great way to honor the legacy of Dr. King and to show solidarity with the principles of freedom and equality that he stood for. The event typically includes a run or walk of various distances, suitable for participants of all ages and fitness levels. It's a day of community, commemoration, and physical activity, often concluding with speeches, performances, or other community events.

Ice Skating in Millennium Park

Ice skating in Millennium Park is a quintessential winter activity in Chicago. January is the perfect time to enjoy the rink as the holiday crowds have thinned out, but the festive atmosphere still remains. Not only do you get to have fun and exercise, but you also get to do so in the heart of the city with the stunning Chicago skyline as your backdrop. Plus, the rink offers free admission - you only need to pay if you're renting skates. Whether you're a seasoned skater or a first-timer, it's an experience not to be missed.

Which Chicago January events are you going to?



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