The 4 Best Christmas Experiences & Tours in Chicago
Chicago turns into a winter wonderland during the holidays, with its iconic skyline decorated in lights and a variety of festive activities that make the city so special in December. From twinkling Christmas trees and bustling markets to elegant dinner cruises on Lake Michigan, Chicago offers a rich mix of experiences that capture the spirit of the season. Whether you’re after a fun downtown walk, a romantic cruise, or an in-depth exploration of the Loop’s holiday highlights, there’s something here for you.
What makes Chicago unique during Christmas is its blend of big-city spectacle and cozy traditions. You can stroll past world-famous department stores like Macy’s, admire the massive holiday windows, or enjoy the glow of thousands of lights across the city’s historic architecture. For those seeking a more immersive experience, guided tours reveal stories and secrets behind the seasonal decor, making your visit more meaningful. For a quick overview of what’s available, check out these festive tours, dinner cruises, and lights journeys.
1. The Christmas Tree Crawl Experience Chicago at the Holidays
At number 1, the Christmas Tree Crawl Experience offers a lively, two-hour adventure through downtown Chicago’s most stunning holiday displays. For just $35 per person, you’ll walk about 1.5 miles, stopping at the famed Christkindlmarkt and the historic Marshall Field’s building, along with several lesser-known spots with captivating holiday decor. Your guide, Hillary, or Heath, will share stories behind many of Chicago’s Christmas traditions and decorate ideas, giving you insights that make each tree and ornament more meaningful.
What makes this tour stand out is its combination of sightseeing and storytelling, plus the chance to taste holiday sweets along the way. Guests consistently praise the energetic guides, with one reviewer noting, “He was fun and knew a lot,” while another appreciated the tour’s cheerful atmosphere despite the cold. The small group setting creates a friendly, personalized experience, and the included treats add a festive touch. Perfect for those who enjoy walking, learning local history, and seeing the city’s holiday spirit up close.
Bottom Line: This tour delivers a lively, easy way to enjoy Chicago’s iconic Christmas trees and decorations, perfect for inquisitive travelers who want a warm, engaging experience.
2. Chicago: Christmas Eve Lake Michigan Gourmet Dinner Cruise
Next, the Christmas Eve Dinner Cruise offers an elegant way to celebrate the holiday on Lake Michigan. For $193, you get a three-course plated dinner served at a private table, along with live DJ entertainment and panoramic views of Chicago’s skyline. As the boat cruises past landmarks like Navy Pier and Willis Tower, you’ll enjoy the shimmering city lights reflected on the water.
What sets this experience apart is its combination of fine dining and scenic cruising. It’s ideal for couples or anyone wanting a romantic, upscale holiday outing. The reviews highlight the impeccable service, with one guest mentioning how stunning the city views were from the outer decks during sunset. The cruise lasts about 2.5 hours, making it a perfect way to unwind after a busy day or as a special Christmas Eve celebration. The only potential downside is the price, but for many, the luxury and unique perspective on the city justify the cost.
Bottom Line: If you’re seeking a sophisticated, scenic holiday dinner with great views and a festive atmosphere, this cruise offers a memorable experience—especially on Christmas Eve.
3. Chicago’s Festive Lights: A Magical Christmas Journey
At number 3 is Chicago’s Festive Lights: A Magical Christmas Journey, which focuses on exploring the city’s beautifully decorated neighborhoods and landmarks. Meeting at American Girl Place on Michigan Avenue, the tour ends at the Christkindlmarket, giving you a comprehensive look at Chicago’s holiday lighting and decoration scene.
While there are no reviews listed yet, this tour stands out for those who want an immersive experience that combines walking through lit-up streets and learning about local holiday traditions. The roughly two-hour tour covers notable spots like Navy Pier’s holiday displays, and it’s ideal for families or anyone who wants to see Chicago’s festive side with a guide explaining what makes each location special.
Bottom Line: Perfect for those who want an overview of Chicago’s holiday lighting and decorations, especially if you enjoy walking and discovering the city’s seasonal charm in a guided group.
4. Chicago Christmas Loop Tour
Last but not least, the Chicago Christmas Loop Tour offers a one-and-a-half to two-hour deep dive into the heart of downtown Chicago. Led by Kevin, who brings over 50 years of local knowledge, this tour covers iconic sites like Macy’s on State Street—home to the world’s largest Tiffany mosaic—and the historic Palmer House Hilton.
What makes this tour particularly appealing is how it reveals the stories behind the city’s famous architecture and holiday displays. Visitors rave about Kevin’s ability to make history fun and relevant, turning a simple walk into a lively storytelling session. The tour also visits the Marquette Building and the Christkindlmarket, giving a well-rounded view of Chicago’s Christmas traditions. Because it’s a small-group experience, it’s flexible and personal, great for those wanting an educational, engaging holiday outing.
Bottom Line: This tour offers a rich, historical perspective on Chicago’s Christmas scene, ideal for travelers who appreciate storytelling and architecture.
How to Choose the Best Christmas Tour for You
When selecting your holiday experience, consider your budget, interests, and physical comfort. If you love walking and festive decor, the Christmas Tree Crawl is a fun, affordable option. For a romantic, upscale celebration, the Lake Michigan dinner cruise provides a memorable evening, especially on Christmas Eve. Those interested in history and architecture will enjoy the Loop tour, which combines storytelling with city sights.
Booking early is advisable, particularly for popular options like the dinner cruise, which can sell out quickly during the holidays. If you prefer a shorter, more relaxed experience, the Festive Lights tour offers a flexible way to see Chicago’s holiday decorations without a long commitment.
Final Thoughts
Chicago provides a diverse range of Christmas experiences—from lively walks and scenic boat cruises to architectural history and festive light displays. For those wanting a lively, social event, the Christmas Tree Crawl is a perfect introduction. If you’re seeking elegance and romance, the Lake Michigan dinner cruise is hard to beat. For a deeper dive into the city’s holiday stories and architecture, the Loop tour offers a memorable, educational experience.
No matter your choice, booking early will help ensure you get your preferred experience. These tours showcase Chicago’s holiday spirit and make unforgettable memories—so pick what suits your style and enjoy a truly festive Chicago Christmas.