Experience the Magic of Chicago This Holiday Season

on Our Festive Tours from Toronto, Canada

Looking for a magical holiday getaway without the stress of driving or planning? Our bus tours from Toronto to Chicago offer the perfect blend of festive experiences, rich culture, and historical charm. Whether you're a fan of architecture, love holiday markets, or simply enjoy a cozy bus ride through scenic routes, this tour has something for everyone—especially seniors who are looking for a relaxed yet enriching experience.

Discover Chicago During the Most Wonderful Time of the Year

Chicago is famous for its vibrant culture, breathtaking skyline, and world-class attractions, but the city truly comes to life during the holiday season. Millions of people flock to Chicago to experience its iconic holiday traditions. From the dazzling lights of Millennium Park to the historic Palmer House Hotel’s festive decor, our bus tour will give you an unforgettable Chicago Christmas experience.

Christkindlmarket: A German Holiday Tradition

One of the highlights of this bus tour from Toronto is a visit to the famous Christkindlmarket. Situated in Daley Plaza, this outdoor holiday market brings a touch of old-world Europe to the heart of Chicago. Modeled after the traditional markets of Nuremberg, Germany, Christkindlmarket is filled with colorful wooden stalls where vendors sell handcrafted gifts, ornaments, and delicious seasonal treats.

Imagine sipping hot glühwein (mulled wine) from a collectible souvenir mug, snacking on freshly baked pretzels, or sampling roasted nuts as you browse through the many unique gifts on offer. The market also features live music and entertainment, making it a fun and festive way to spend the day.

And don’t forget to admire Chicago's dazzling official Christmas tree, located right next to the market. This massive, hand-selected tree is the centerpiece of holiday celebrations in the city.

The Iconic Palmer House Hotel & Macy’s on State Street

No trip to Chicago during the holidays is complete without a visit to the historic Palmer House Hotel. Opened in 1927, the French Empire-style lobby is a feast for the eyes, with intricate Tiffany glass designs and stunning holiday decorations that transport you back in time. The hotel has hosted some of the biggest names in entertainment history, including Frank Sinatra, Ella Fitzgerald, and Louis Armstrong, and you’ll get a guided tour of its most famous rooms, including the legendary Empire Room.

After exploring the Palmer House, take a short walk to Macy’s on State Street, one of the largest department stores in North America and a Chicago landmark. Formerly known as Marshall Field’s, this historic store is decked out in holiday splendor, and its window displays are a seasonal favorite. Be sure to check out the famous Tiffany Mosaic, the largest of its kind in the world, and shop for gifts to take back home.

The Walnut Room: A Holiday Dining Experience

A special part of our Chicago bus tour from Toronto is a meal at the Walnut Room, a Chicago institution that dates back to 1907. Located inside Macy’s on State Street, the Walnut Room was the first-ever restaurant opened in a department store. Here, you’ll dine under the glittering lights of a massive Christmas tree while savoring a traditional meal featuring the famous Mrs. Hering’s Chicken Pot Pie.

As an extra treat, each tour member will receive a complimentary box of Frango Mints, a Chicago specialty originally made in the store.

Millennium Park and the Famous "Bean"

On the second day of the tour, start your morning with a visit to Millennium Park, home to the world-famous Cloud Gate (better known as “The Bean”). This iconic reflective sculpture offers perfect photo opportunities, especially when surrounded by festive lights and holiday decorations.

Millennium Park is also home to an outdoor ice-skating rink, although for our senior travelers, there’s plenty to enjoy just by strolling through the park and taking in the holiday atmosphere. It’s a peaceful yet vibrant way to experience the city.

Chicago Architecture Tour: A Journey Through Time

Chicago is often regarded as the birthplace of modern architecture, and our guided Chicago Architecture Tour will give you an up-close look at the city’s most famous buildings. From the striking Wrigley Building and the historic Tribune Tower to the modern Aqua Tower, you’ll learn how Chicago’s skyline came to be and why it’s considered one of the most beautiful in the world.

The tour includes a visit to the Chicago Riverwalk, a scenic spot that offers some of the best views of the city’s skyscrapers. With the Chicago River flowing through the heart of downtown, the Riverwalk is particularly charming during the holiday season when it's illuminated with festive lights.

Art Institute of Chicago: Holiday Highlights

A visit to the Art Institute of Chicago is a must on any trip to the city, especially during the holidays. This world-renowned museum is home to famous works of art such as Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.” But during the holiday season, the museum takes on an even more magical atmosphere with its special holiday exhibits.

One of the most beloved holiday traditions is the decorated Thorne Miniature Rooms, which showcase dollhouse-sized replicas of historical rooms, all decked out for the season. And don’t forget to snap a photo with the museum’s famous lion statues, which are adorned with festive wreaths.

Michigan Avenue: The Magnificent Mile

There’s no better way to end your Chicago adventure than with some last-minute holiday shopping on Michigan Avenue, also known as the Magnificent Mile. This iconic stretch of road is home to some of the city’s best shops, from high-end boutiques to department stores like Nordstrom and Neiman Marcus.

During the holiday season, Michigan Avenue is lit up with thousands of twinkling lights, creating a magical shopping experience. Whether you’re looking for gifts for loved ones or a special souvenir to remember your trip, this bustling street has it all.

🧡 Book now to secure your spot and make this holiday season one to remember!