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Experience the Magic of the Holidays in Chicago: A Perfect Long Weekend Getaway

Updated: Dec 30, 2024

As the air turns crisp and holiday cheer fills the streets, there’s no better place to celebrate the season than in the Windy City. Whether you're a local or just visiting, Chicago offers an array of festive activities that will make your long weekend unforgettable. Let’s dive into how you can embrace the holiday spirit in Chicago. 


Where to Stay: The Waldorf Astoria Chicago 


Start your holiday getaway with luxury and comfort at the Waldorf Astoria Chicago. Located in the heart of the city, this elegant hotel offers a serene retreat amid the bustling holiday festivities. Indulge in their exquisite spa services or simply relax in your beautifully appointed room. The hotel’s proximity to downtown attractions makes it an ideal base for your holiday adventures.


Savor a Holiday Themed Afternoon Tea


Experience a classic holiday tradition by enjoying a holiday tea at either The Drake Hotel or The Peninsula Chicago. These timeless hotels offer a festive ambiance with beautifully decorated tea rooms, where you can savor an array of delicious pastries, finger sandwiches, and, of course, a perfect cup of tea. It's a lovely way to recharge before heading back into the holiday hustle and bustle. 



Visit the Christkindl Market 


No holiday visit to Chicago is complete without stopping by the Christkindl Market at Daley Plaza. Running from November 22 to December 24, the market is open Sunday to Thursday from 11 AM to 8 PM and Friday to Saturday from 11 AM to 9 PM. On special days like Thanksgiving and Christmas Eve, the market is open from 11 AM to 4 PM. Explore charming stalls filled with handmade crafts, delicious seasonal treats, and even try your hand at making a glass-blown ornament. It’s a perfect spot for finding unique gifts and soaking in the festive atmosphere. 


Image by: Daniel X. O'Neil from USA via Wikimedia Commons
Image by: Daniel X. O'Neil from USA via Wikimedia Commons

Image by: Krebs Glas Lauscha via Wikimedia Commons
Image by: Krebs Glas Lauscha via Wikimedia Commons

Image by: Nyuso Za Nairobi via Wikimedia Commons
Image by: Nyuso Za Nairobi via Wikimedia Commons

Lincoln Park Zoo Lights 

For a magical light display, head over to the Lincoln Park Zoo Lights, running from November 15 to January 5. The zoo transforms into a winter wonderland featuring millions of twinkling lights, festive displays, and fun activities that are sure to dazzle both kids and adults alike. 


Image by: Marit & Toomas Hinnosaar via Wikimedia Commons
Image by: Marit & Toomas Hinnosaar via Wikimedia Commons

Image by: Andrew Wilkinson
Image by: Andrew Wilkinson

Learn about Christmas Around the World at MSI 

Expand your holiday experience by visiting the Museum of Science and Industry for the annual Christmas Around the World exhibit, which takes place from November 16 to January 6. Explore beautifully decorated trees representing different cultures, all adorned with unique ornaments and symbols of the season. It’s an educational and heartwarming way to appreciate global holiday traditions. 


Image from Wikimedia Commons
Image from Wikimedia Commons

Ice Skating Fun 

Don’t miss out on the quintessential winter activity of ice skating at either Millennium Park or Maggie Daley Park. Glide across the ice surrounded by the festive skyline and the twinkling lights, making for a memorable holiday experience. 


Image by: Machael Barera via Wikimedia Commons
Image by: Machael Barera via Wikimedia Commons

Joffrey Ballet Chicago: The Nutcracker 

One of the highlights of the season is the Joffrey Ballet’s production of The Nutcracker from December 6 to 28. This enchanting performance is a must-see, bringing the classic tale to life with breathtaking choreography and stunning sets. Be sure to book your tickets early, as they tend to sell out quickly! 


Image from KCBalletMedia via Wikimedia Commons
Image from KCBalletMedia via Wikimedia Commons

Shopping and Window Displays 

Take some time to shop for gifts and enjoy the stunning holiday window displays along The Magnificent Mile. This iconic shopping district pulls out all the stops during the holiday season, showcasing elaborate decorations and displays that will inspire your Christmas spirit. 


Image by: Vishal Shah
Image by: Vishal Shah

Holiday Sing-Along at Cloudgate 

Cap off your festive weekend by attending the Holiday Sing-Along at Cloudgate in Millennium Park. Held on Fridays in December from 6 to 7 PM, this joyous event invites everyone to join in singing beloved holiday classics, creating a sense of community and merriment. 


Image by: Shelby L Bell via Wikimedia Commons
Image by: Shelby L Bell via Wikimedia Commons

With so much to see and do, a long weekend spent celebrating the holidays in Chicago is sure to create lasting memories. From cultural experiences and breathtaking displays to delicious treats and festive cheer, there’s something for everyone to enjoy. So, pack your bags and get ready for an unforgettable holiday escape in the heart of the city!


Are you ready to embark on your own luxury adventure? Contact me today, and let me curate your next unforgettable vacation.

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