Valerie Wilson Travel


Chicago stands tall as one of America’s most iconic cities. From its towering skyscrapers, including the famous Willis Tower and John Hancock Center, to the serene beauty of Millennium Park and the eclectic neighborhoods known for their culinary scenes. Chicago is a mosaic that marries tradition with innovation. During the holiday season, Chicago comes to life and offers a huge variety of experiences that make it a must-visit destination.  

What We’d Do:
Go to Sawada Coffee in the West Loop

Sawada Coffee stands out as one of the most enchanting coffee spots in Chicago. Begin your morning with a stroll along Green Street, where you’ll discover world-renowned coffee. The ambiance and lighting create an inviting setting, perfect for gathering friends in the heart of the windy city. If you are not a coffee person, Green Street has many options for food and drinks. Grab a bite across the street at The Allis Chicago, located in Soho House Chicago, for a lux environment and fantastic cuisine experience. 

Visit Chicago’s Christkindlmarket (Christmas Market)

Named one of the Best Christmas Markets in the US for 2023, Chicago’s Christkindlmarket is an enchanting and immersive experience in the city. The market beautifully showcases the rich cultural heritage of Chicago’s German community. Historically in Daley Plaza, this year’s festivities include a location in Wrigleyville. You can enjoy the cheerful ambiance, live entertainment, and cultural depth behind each stall. Discover the amazing food vendors and charming holiday gifts, perfect for sharing the festive cheer with your loved ones. 

Check off Bucket List Items at Millennium Park

Explore and check off your Chicago bucket list items in Downtown Chicago. Begin with historically iconic spots like Millennium Park, home to the “Bean” and The Art Institute of Chicago. Near this area you will find people walking, strolling, and biking along Lake Michigan. As you venture further, enjoy the picturesque River Walk and Magnificent Mile, where the stunning skyline provides the perfect backdrop for your adventures. 

Where We’d Stay:
Park Hyatt Chicago

Quintessentially Chicago with deep historical roots and a landmark address, the reimagined Park Hyatt Chicago is a residential oasis for discerning global travelers seeking a uniquely authentic, downtown experience. A luxurious home away from home with sprawling views of Lake Michigan, Park Hyatt Chicago embraces the elements of the surrounding city while offering a serene escape through thoughtfully calming design and authentic local experiences. Park Hyatt, where the world sees Chicago and Chicago sees the world. 

The Langham, Chicago

The Langham, Chicago – housed within a 52-story landmark tower designed by renowned architect Mies van der Rohe – gracefully blends urban sophistication with refined luxury. Conveniently located downtown, the hotel is a short walk from the boutique-lined boulevards of Chicago’s retail hub – The Magnificent Mile – and many premier sites, including The Loop, Millennium Park, Grant Park, and Navy Pier. Featuring 316 luxurious guest rooms boasting views of the iconic cityscape and the Chicago River, The Langham, Chicago offers innovative amenities, exceptional attention to detail, and fittings to create a luxurious and relaxing retreat.

Ready to book your Chicago getaway?