Winter in Chicago is truly a magical time. The city lights up, cools down, and is often blanketed in snow, inviting picturesque walks through downtown followed by cozy café stops for steaming mugs of cocoa. Get the most out of the season by participating in the city’s most popular holiday traditions.
It’s not Christmas in Chicago without experiencing all the Loop has to offer. Embrace the city center by checking out this list of annual winter events, and be sure to visit the Christkindlmarket in Daley Plaza, a German-inspired market twinkling with Christmas trinkets and traditional food. Also, make your way to Millennium Park for a picture with Chicago’s giant Christmas tree, decorated with nearly 50,000 multi-colored lights. Spend an afternoon skating laps at the McCormick Tribune Ice Rink or skate a path down the Maggie Daley Ice Ribbon.
There’s something to be said for walking down Michigan Avenue in the winter after dark. The barren trees that line the sidewalks are illuminated with millions of sparkling white lights to set the mood for shoppers buying their perfect holiday presents. And don’t forget a tour of Macy’s famous themed Christmas windows on State Street. Grab a cup of hot chocolate or another cozy beverage for the journey from one of the city’s finest while you’re at it.
Destinations Unlocked:Let our travel expert Stefano help you find your perfect Culture trip
Looking for an expert's perspective?Uncover my top 3 recommended places from each continent on the map.
1. GuatemalaAn express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.
2. BelizeA quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
3. MexicoAn exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
1. EcuadorA remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.
2. PeruAn alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
1. ItalyThe ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.
2. ScotlandEmbark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
3. PortugalA wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
1. South KoreaDiscover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.
2. ThailandFrom Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
3. Sri LankaA fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
1. MoroccoAn epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!
2. EgyptFrom Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
If you need to be fully immersed in the holiday spirit, delve into Chicago’s theater scene. It’s packed with Christmas shows that will keep you busy from now until the new year. For Chicago classics, stop in at the Joffrey Ballet’s The Nutcracker and Goodman Theatre’s A Christmas Carol. Also, get your tickets for It’s A Wonderful Life: Live in Chicago!, A Charlie Brown Christmas, and Barney the Elf.
You’re going to need transportation for all this Christmas fun, and it doesn’t have to be tedious. Just hop aboard the CTA’s Holiday Train to feel like you’re on your way to the North Pole. This unique Chicago tradition decks out a full L train with holiday lights, decorations, music, and costumed employees bringing joy to the entire city. They also run a Holiday Bus, and for the first time, this year will have an Elves’ Workshop Train in service as well. The themed transit runs on a specific schedule through December 23rd, which you can check out on the CTA website.
Chicago is a city rampant with family-friendly fun, but this next tradition is strictly for the 21-and-over crowd. For the past 20 years, thousands of Christmas-enthused young people have descended on Wrigleyville each December for The Twelve Bars of Xmas Bar Crawl. Also known as TBOX, this all-day party kicks off at 8 AM on December 10th and continues long into the night. Attendees come decked out in their best holiday outfits which go far past the typical ugly Christmas sweater. Expect to see over-the-top costumes including lights, moving parts, and plenty of bells. It’s fun to drive past it, be a part of it, and know it ultimately goes to a good cause; TBOX has raised more than $250,000 for local charities over the years.
No matter what you decide to do this Christmas, always surround yourself in good company. Join in together on the do-good holiday spirit and be sure to give back whenever possible.
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WHAT DO YOU LOVE ABOUT YOUR JOB?
It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
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I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!
Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
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Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.