Chicago’s Christmas season shines with practical, memorable experiences that won’t break the bank. The Christmas Tree Crawl tops my list – it’s a smart way to explore downtown’s holiday displays while learning about international traditions. I especially love the Private Festive Lights Tour for avoiding tourist crowds and catching the best photo opportunities of the city’s illuminations. The Christmas Loop Tour efficiently combines two must-sees: the authentic German-style Christkindlmarkt and the Loop’s architectural treasures. For a special occasion, the Christmas Eve dinner cruise offers both city views and a traditional holiday meal. Read on for our carefully selected tours that showcase Chicago’s holiday magic at its best.
Good To Know
- The Christmas Tree Crawl Experience offers a festive and educational walking tour to explore global Christmas traditions.
- The Festive Lights Tour provides a private, guided tour showcasing the holiday illuminations of Chicago, including a visit to Christkindlmarket.
- The Chicago Christmas Loop Tour features a 1.5-mile walking tour through downtown Chicago, highlighting the Christkindlmarkt and iconic architecture.
- The Christmas Eve Dinner Cruise on Lake Michigan offers a plated dinner experience with a 3-hour duration and a maximum capacity of 150 guests.
- The Christmas Eve Brunch Cruise on the Chicago River provides a 3-hour, chef-prepared, 3-course holiday menu with DJ entertainment for up to 200 guests.
The Christmas Tree Crawl Experience Chicago at the Holidays
For those seeking a festive and educational holiday experience in Chicago, the Christmas Tree Crawl provides a delightful opportunity.
The tour showcases famous and lesser-known Christmas trees and decorations, including visits to Christkindlmarkt and Marshall Field’s. Travelers will learn about global Christmas stories and traditions while enjoying holiday sweets.
With a 92% recommendation rate, the 2-hour walking tour covers 2 miles and accommodates up to 20 guests. Priced from $35 per person, the experience includes a local guide, snacks, and special treats.
While not wheelchair accessible, the tour offers a fun and informative way to discover Chicago’s impressive holiday decor.
Read our full review: The Christmas Tree Crawl Experience Chicago at the Holidays Review
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Chicago’s Festive Lights: A Magical Christmas Journey
Chicago’s Festive Lights: A Magical Christmas Journey offers a captivating exploration of the city’s dazzling holiday illuminations.
This private tour, priced from £265.96 per person, takes visitors on a magical journey through the heart of Chicago. Starting at the iconic American Girl Place, the tour guides participants to breathtaking light displays, culminating at the renowned Christkindlmarket.
With a private guide providing insider knowledge, the tour is accessible to most travelers and conveniently located near public transportation.
Operated by Opatrip.com USA, this experience is likely to sell out, so early booking is recommended. Travelers can reserve now and pay later, with a lowest price guarantee.
Read our full review: Chicago’s Festive Lights: A Magical Christmas Journey Review
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Chicago Christmas Loop Tour
The Chicago Christmas Loop Tour offers a festive jaunt through the heart of the city, immersing visitors in the enchanting holiday atmosphere.
This 1.5-mile walking tour explores the iconic sights of downtown Chicago, including the famous Christkindlmarkt, a unique shopping destination featuring German cuisine.
Travelers can expect to be surrounded by stunning architecture and the iconic Picasso statue while enjoying a warm German pretzel.
With a maximum group size of 10, the tour runs daily at 5:00 PM and is priced from $80 per person.
While not wheelchair accessible, the tour is close to public transportation and requires a moderate fitness level.
Confirmation is provided at booking, and free cancellation is available up to 24 hours in advance.
Read our full review: Chicago Christmas Loop Tour Review
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Christmas Eve Plated Dinner Cruise on Lake Michigan
On Christmas Eve, travelers can embark on a delectable plated dinner cruise along the serene waters of Lake Michigan. The 3-hour event offers a maximum of 150 guests a private transportation experience with dinner, gratuities, and beautiful views of the Chicago skyline.
The cruise departs at 7:00 PM from the meeting point at 600 E Grand Ave and returns to the same location. The experience is wheelchair accessible, near public transportation, and suitable for most travelers, including those with infant seats.
Bookings are confirmed within 48 hours, though the tickets are non-refundable. Priced from $184.26 per person, the Christmas Eve Plated Dinner Cruise promises an unforgettable holiday celebration on the waters of Lake Michigan.
Read our full review: Christmas Eve Plated Dinner Cruise on Lake Michigan Review
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Christmas Eve Chicago River Plated Brunch Cruise
For travelers who want to continue the Christmas Eve celebration on the water, the Chicago River Plated Brunch Cruise offers a delightful alternative to the Lake Michigan dinner cruise.
The 3-hour cruise departs at 12:30 PM and includes a chef-prepared, 3-course plated holiday menu, DJ entertainment, and complimentary coffee, hot tea, and iced tea.
The cruise is wheelchair and stroller accessible, allows service animals, and has infant seats available.
With a maximum of 200 travelers, the cruise provides an intimate setting to enjoy the sights of the Chicago River on Christmas Eve.
Confirmation is received at the time of booking.
Read our full review: Christmas Eve Chicago River Plated Brunch Cruise Review
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The Sum Up
Chicago offers a variety of festive experiences to make your Christmas memorable. From exploring the city’s iconic holiday decorations to indulging in a riverboat cruise, there’s something for all. Whether you’re looking for a magical journey or a cozy dinner, Chicago’s Christmas offerings provide the perfect blend of tradition and modern excitement.