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The 5 Best Christmas Tours & Experiences in Chicago
Chicago becomes especially magical during the holiday season. Its towering skyscrapers are draped in lights, streets fill with the scent of roasted chestnuts and hot cocoa, and the city’s iconic architecture is transformed with Christmas cheer. For those wanting to see the city in its holiday best, Chicago offers a variety of tours—from lively walking adventures to elegant dinner cruises—that capture the festive spirit. We particularly enjoy the Christmas Tree Crawl Experience for its fun, local storytelling, and the Lake Michigan Dinner Cruise for a romantic, waterside celebration. Whether you're after dazzling lights or cozy markets, Chicago’s holiday offerings won’t disappoint.
If you’re trying to decide between a walking tour, a scenic cruise, or a private experience, this guide will help you pick the perfect Christmas adventure. We’ve gathered the top options, including insider favorites like the Christmas Tree Crawl Experience Chicago at the Holidays and the Chicago Christmas Loop Tour. Keep reading to find the best fit for your holiday plans.
Quick Overview
This list covers a range of Christmas experiences in Chicago, from walking tours that explore holiday decorations and stories to elegant dinner cruises on Lake Michigan, and private light journeys through the city’s most iconic streets. Highlights include visits to Chicago’s famous Christmas trees, stops at the Christkindlmarket, and spectacular views of the skyline decorated for the holidays. If you're visiting Chicago during December, these tours offer a mix of local traditions, festive sights, and unique experiences that bring the city's holiday spirit alive.
Now, let’s dive into the details of each tour so you can choose which one suits your holiday style best.
1. The Christmas Tree Crawl Experience Chicago at the Holidays
Starting with the most cheerful of Chicago’s holiday activities, the Christmas Tree Crawl Experience offers a lively walk through downtown Chicago to see the city’s most famous and lesser-known Christmas trees. With a 5.0/5 rating from 23 reviews, this two-hour tour is perfect for anyone who loves holiday decorations and storytelling. Your guide will lead you around the Loop, stopping at the Christkindlmarkt, the historic Marshall Field’s building, and several hidden spots with stunning holiday decor.
What makes this tour stand out is its celebratory atmosphere and the storytelling component. You’ll hear about Christmas traditions from around the world, making the experience both festive and educational. Included are holiday sweets, so you won’t go hungry during the 1.5 miles of walking. Guests praise the guide’s enthusiasm and local knowledge, with comments like “He was fun and knew a lot,” and “Hillary’s charm made the tour memorable.”
This tour is ideal for those who want a short, lively introduction to Chicago’s holiday spirit without leaving the city center. It’s a budget-friendly option at just $35 per person, offering rich stories, beautiful decorations, and sweet treats.
Bottom Line: Perfect for casual visitors and families wanting a festive walk, this tour combines Chicago’s holiday decorations with local stories and treats.
2. Chicago: Christmas Eve Lake Michigan Gourmet Dinner Cruise
For a romantic and memorable holiday experience, the Christmas Eve Dinner Cruise on Lake Michigan is hard to beat. This 2.5-hour cruise features a gourmet 3-course dinner, crafted to elevate your Christmas Eve. As you drift along Lake Michigan, you’ll enjoy panoramic views of Chicago’s skyline—including Navy Pier, Willis Tower, and the illuminated cityscape.
The cruise includes an onboard DJ and a lively atmosphere, making it more than just a scenic ride. Guests can relax at a private table and sip on creative cocktails while soaking in the festive city sights. The experience is perfect for couples celebrating a special holiday or groups seeking a refined, waterside Christmas celebration. The reviews note the impeccable service and the ability to enjoy the city from a different perspective.
At $199 per person, this dinner cruise offers exceptional value for a holiday on the water. It’s best suited for those who appreciate fine dining, stunning views, and a touch of elegance on Christmas Eve.
Bottom Line: An elegant, scenic dinner cruise that combines gourmet food with spectacular views, ideal for romantic holidays or special occasions.
3. Chicago’s Festive Lights: Private Magical Christmas Journey
If you’re after a personalized experience that showcases Chicago’s holiday lights, the Private Magical Christmas Journey is a fantastic choice. Starting at 875 North Michigan Avenue and ending at Christkindlmarket, this two-hour private tour offers a customized view of the city’s most iconic holiday scenes.
Your private guide will lead you through the glowing streets of N State St, with stops at the Chicago Skyscraper in holiday splendor. The atmosphere is enhanced by the sounds and scents of a traditional German Christmas market at Christkindlmarket. What makes this tour unique is the private setting, allowing for a more intimate and flexible experience—perfect for families, couples, or small groups.
Costing $1,303 for up to four people, it’s a premium experience but offers the chance to explore Chicago’s holiday lights at your own pace. Reviewers enjoy the luxury of a private guide and the opportunity to see the city’s decorations without the crowds.
Bottom Line: Best suited for small groups or couples wanting a tailored, private tour of Chicago’s festive displays and markets.
$1,303 per group up to 4
4. Chicago Christmas Loop Tour
The Chicago Christmas Loop Tour brings you into the heart of downtown Chicago for a 1.5 to 2-hour exploration of the city’s holiday highlights. Led by Kevin, who has five decades of experience, this tour is designed to explain the “why” behind Chicago’s Christmas displays. It’s a great choice if you want an educational, storytelling approach to the city’s seasonal decorations.
Your tour begins at Macy’s on State Street, where you’ll see the largest Tiffany mosaic and the Great Tree, along with the animated windows. You’ll also visit the Palmer House Hilton’s historic lobby and the Marquette Building, admiring their Tiffany mosaics and architecture. The highlight is the Christkindlmarket, where you can enjoy international shopping and hot mulled wine. All stops are free, and the tour balances history, architecture, and festive sights.
While it currently has no reviews, it seems like a perfect choice for those who enjoy Chicago’s architecture and holiday traditions with a knowledgeable guide. It’s a good value at $80 per person, especially for those interested in the city’s stories behind the decorations.
Bottom Line: A compact, informative tour ideal for architecture lovers and history buffs wanting to experience Chicago’s Christmas in the Loop.
$80.00 per person
5. Chicago’s Festive Lights: A Magical Christmas Journey
Finally, the Festive Lights: A Magical Christmas Journey offers a luxury experience with a start point at American Girl Place and ending at Christkindlmarket. For $374.69 per person, this two-hour tour promises a premium, tailored holiday experience with a focus on personalized sightseeing.
This tour emphasizes a more exclusive style of exploring Chicago’s Christmas lights and markets, with a more refined approach than larger group tours. It’s suited for travelers wanting a private or semi-private setting with the flexibility to customize their holiday viewing. The detailed itinerary includes the city’s most iconic spots, all within a comfortable setting.
Given the price, it’s best suited for those celebrating special occasions or wanting a high-end, private experience. As there are no reviews yet, it’s harder to gauge customer satisfaction, but the price suggests a very personalized service.
Bottom Line: Ideal for travelers seeking an exclusive, customized experience of Chicago’s holiday lights and markets.
$374.69 per person
How to Choose the Right Christmas Experience in Chicago
Choosing among these options depends on your budget, interests, and group size. If you love walking and storytelling, the Christmas Tree Crawl offers great value and fun. For a romantic or special dinner, the Lake Michigan Dinner Cruise is hard to beat. Want something more private? The Magical Christmas Journey or Festive Lights give you tailored experiences, though at a higher price point.
Consider your time constraints—a quick 1.5-hour tour like the Loop experience suits a tight schedule, while a dinner cruise or private journey offers a more relaxed, immersive outing. Think about who you’re traveling with; families might love the lively decorations and stories, while couples may prefer the romantic waterside cruise.
Booking early is wise, especially for the dinner cruise and private tours, as they tend to fill up fast during the holiday season. Also, check the weather forecast—some tours, like the dinner cruise, are weather-dependent.
Final Thoughts
Chicago truly shines during the Christmas season, whether through its twinkling streets, lively markets, or elegant dinners. If you’re after an interactive walking experience, the Christmas Tree Crawl Experience is a festive hit. For something more upscale and scenic, the Lake Michigan Dinner Cruise provides a memorable waterside celebration. And for those seeking a tailored, private view of the city’s holiday lights, the exclusive journeys are hard to beat.
No matter your preference, Chicago offers a holiday experience suited to every traveler. Be sure to book early, especially for the more premium options, and prepare for a Christmas season full of lights, stories, and festive charm that will make your visit truly special.