Chicago in January offers a magical blend of winter charm and vibrant city life. Whether you’re visiting for the first time or are a seasoned traveler, this guide will help you plan your trip, stay comfortable, and experience some of the city’s best activities.
Planning a trip to Chicago this January? Here are some resources to help you design your own itinerary!
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What to Do in Chicago in January 2025
Bulls Basketball at United Center
Nothing beats the excitement of watching the Chicago Bulls play at the United Center. The energy of the fans and the high-paced action make it an unforgettable experience. Be sure to grab some classic stadium snacks while you’re there! If you’re visiting with friends or family, this is a fantastic bonding activity. Pro tip: Arrive early to explore the United Center’s statues and memorabilia dedicated to Chicago’s sports legends.
Drunk Shakespeare Chicago
If you’re looking for a night of comedy and entertainment, Drunk Shakespeare is a must-see. Talented actors mix drinks with dramatic flair, offering a hilarious and interactive twist on Shakespearean classics. It’s located near the Theater District, making it a great addition to an evening downtown. Arrive early to grab the best seats and enjoy pre-show cocktails. It’s perfect for adults seeking a unique and laughter-filled evening.
Neon Brush Kids Chicago: Family Painting Experience Tickets
For families with young children, the Neon Brush Kids experience provides a creative outlet. Kids can express themselves with guided painting sessions in a vibrant and welcoming environment. Parents will enjoy the opportunity to relax while their little ones immerse themselves in art. The studio provides all materials, making it a hassle-free way to create lasting memories. Plus, you’ll get to take home your child’s masterpiece as a cherished keepsake.
The Escape Game Chicago: Epic 60-Minute Adventures Tickets
Challenge yourself and your group with this highly engaging escape room experience. Each room features intricate puzzles and immersive themes, from heist adventures to futuristic escapades. It’s a perfect indoor activity for friends and families. Collaborate to solve clues, beat the clock, and feel the thrill of success together. These rooms are designed to cater to various skill levels, ensuring everyone can contribute.
Spray Paint ‘n’ Sip Urban Art Workshop Chicago
Let your creativity flow in this fun and unconventional workshop. Learn the basics of spray-painting techniques while enjoying your favorite beverage. It’s an excellent way to explore urban art and create a one-of-a-kind souvenir to take home. Whether you’re a beginner or a seasoned artist, the instructors ensure an enjoyable experience for everyone. This workshop doubles as a social event, so come prepared to mingle and share ideas.
Candle Making Class On Magnificent Mile (Chicago) Tickets
Warm up with a cozy candle-making class along the Magnificent Mile. Participants get hands-on experience crafting their own candles, experimenting with scents, and learning about the art of wax design. This activity is both relaxing and rewarding. You’ll leave with a personalized candle and newfound appreciation for this craft. The class is ideal for couples, friends, or anyone seeking a therapeutic indoor activity.
Premier Dinner Cruise On Lake Michigan
Wrap up your Chicago visit with a luxurious dinner cruise on Lake Michigan. Savor gourmet dishes, enjoy live entertainment, and marvel at the city’s illuminated skyline. It’s a romantic and memorable way to experience Chicago from the water. Don’t forget to dress warmly, as the lake breeze can be chilly even on enclosed decks. Cruises often feature curated menus, so dietary preferences can be accommodated with advance notice.
Bonus Winter Activities
- Ice Skating at Millennium Park: Glide on the rink surrounded by Chicago’s iconic skyline. Rentals are available on-site, and the festive atmosphere makes it a must-do.
- Winter WonderFest at Navy Pier: Experience indoor winter fun with rides, ice slides, and festive decorations. It’s perfect for families and offers a welcome escape from the cold.
- Chicago Restaurant Week: Indulge in prix-fixe menus at top restaurants and discover the city’s culinary scene. Make reservations early as spots fill up quickly.
- Lincoln Park ZooLights: Wander through dazzling light displays at this free zoo, perfect for a magical evening stroll.
Planning Your Trip in Chicago Like A Pro
Planning is key to enjoying Chicago in January. Here are some tips to make your trip smooth and memorable:
- Check the Weather: Chicago winters can be chilly with temperatures often below freezing. Snow and wind can make it feel even colder, so make sure to pack appropriately.
- Book Early: Popular attractions like museums, tours, and events can fill up fast, especially during weekends. Make reservations for hotels, tickets, and dining in advance.
- Use Public Transport: Chicago’s public transportation system, including the “L” trains and buses, is efficient and budget-friendly. Consider purchasing a Ventra Card for seamless travel.
- Download Essential Apps: Apps like SpotHero for parking (Spot Hero save 15% off using my link), Ventra for public transit, and weather apps can simplify your trip. Additionally, consider apps like Yelp for dining recommendations and Groupon for discounts on activities.
- Plan Indoor and Outdoor Activities: January in Chicago offers a mix of outdoor winter activities and cozy indoor experiences. Balance your itinerary to include both.
Notes While Traveling in Chicago in January
- Layer Up: Dressing in layers will keep you warm and comfortable indoors and outdoors. Thermal undershirts, sweaters, and a heavy coat are essential.
- Carry Cash: Although Chicago is card-friendly, some small vendors or street food stalls might prefer cash.
- Be Mindful of the Wind: The “Windy City” nickname is no exaggeration. A windproof jacket, scarf, and hat are essential to protect you from the chill.
- Time Your Visits: For popular spots like the Willis Tower Skydeck or Millennium Park, aim to visit early in the morning or during weekdays to avoid crowds.
- Explore Indoors: Chicago offers world-class indoor attractions like the Art Institute of Chicago, Shedd Aquarium, and the Field Museum, perfect for staying warm while enjoying the city’s culture.
- Stay Hydrated: Despite the cold, staying hydrated is important, especially if you’re walking around a lot.
- Use Public Facilities: Public restrooms are readily available in major attractions and shopping malls like Water Tower Place. Plan restroom stops to avoid searching in the cold.
What to Pack for Chicago in January
- Warm Clothing: Pack heavy coats, insulated gloves, woolen hats, and scarves. Don’t forget thermal leggings and undershirts for layering.
- Sturdy Footwear: Waterproof boots with good grip are a must for snowy or icy sidewalks.
- Tech Essentials: Keep your camera or smartphone charged for capturing the city’s winter beauty. Pack a power bank to ensure you never run out of battery.
- Travel Essentials: Bring a reusable water bottle, travel-size hand lotion to combat the dry air, and hand warmers for extra comfort.
- Accessories: Sunglasses are handy for bright snowy days, and a small umbrella can be useful for unexpected snow showers.
- Backpack or Tote Bag: Carry your essentials, including snacks, maps, and extra layers, in a lightweight, durable bag.
- Medicines and First Aid: Include a small kit with over-the-counter pain relievers, cold remedies, and any personal prescriptions.
Where To Stay in Chicago
1. TheWIT Hotel: This boutique hotel in the Loop offers modern rooms, a rooftop bar with panoramic views, and proximity to the Theater District and Millennium Park. TheWIT’s unique ambiance makes it a top choice for couples and solo travelers looking for style and convenience. Enjoy the on-site restaurant, which offers a seasonal menu perfect for warming up after a day in the cold.
- Booking your room at theWIT Hotel here
2. Radisson Blu Aqua Hotel: Renowned for its sleek architecture, the Radisson Blu Aqua features luxury amenities, an indoor pool, and easy access to Maggie Daley Park and the Riverwalk. Families and business travelers will appreciate its spacious rooms and excellent location. The hotel also boasts a state-of-the-art fitness center and a relaxing spa.
- Booking your room at Radisson Blue Aqua Hotel here
3. Sable Hotel: Nestled on Navy Pier, this hotel provides breathtaking views of Lake Michigan, contemporary rooms, and a short walk to attractions like the Centennial Wheel. Staying at the Sable Hotel offers the perfect blend of tranquility and excitement. Its unique location ensures you’re surrounded by iconic sights and festive winter activities.
- Booking your room at Sable Hotel here
Chicago in January 2025 is packed with unique experiences that cater to everyone. From sports and art to family-friendly activities and luxury cruises, your trip to the Windy City will be unforgettable. Pack your warm clothes and get ready to explore this vibrant city!
Remember to tag @travelwiththerussells on social media to share your adventures and connect with other travelers.
Enjoy your trip to Chicago and I’m waiting for you to tag me to share your experience!
