Holiday DeLights of Galena & Chicago

Day 1: Chicago

Experience the wonder of the holidays in the heart of Chicago and Galena with this specially curated four day of festive fun.

After pickup and transportation to Chicago, find yourself early afternoon at the charming Christkindlmarket in Daley Plaza, where twinkling lights, handcrafted ornaments, and warm seasonal treats bring Old World holiday traditions to life. Next, explore dazzling cultural displays at the Museum of Science and Industry during Christmas Around the World and Holidays of Lights featuring over 50 beautifully decorated trees representing global holiday traditions. In the afternoon, step into a winter wonderland at Light Up the Lake at Navy Pier. Enjoy sparkling indoor light displays, ice skating, interactive activities, and lakeside holiday shopping. As evening falls, settle in for a heartwarming finale to the evening with It's a Wonderful Life: Live in Chicago! at the American Blues Theater. This live 1940s-style radio performance of the classic holiday tale will leave you filled with joy and nostalgia.

Tonight, rest your eyes at the hotel in Chicago, IL (2 Nights).

Day 2: Chicago

After a hot breakfast, today is all about cozy nostalgia. Begin your morning in the historic Pullman District, where Christmas in Pullman brings the past to life with festive houses, artisan markets, and charming holiday decorations lining the streets of this preserved 19th-century neighborhood. Next, head back downtown for a beloved Chicago tradition, Macy's Holiday Window Displays on State Street. After admiring the animated scenes, head upstairs for a relaxing and elegant lunch beneath the Great Tree at The Walnut Room, a true holiday dining experience. After lunch, stroll through Millennium Park, where the city's official Christmas Tree and festive ice-skating rinks offer postcard-perfect moments in the shadow of Cloud Gate (The Bean). In the late afternoon, treat yourself to a sweet indulgence at Mindy's Hot Chocolate, famous for its rich, artisan cocoa topped with handmade marshmallows in a cozy, inviting setting. As evening falls, head to Lincoln Park Zoo for the spectacular ZooLights display. This family-friendly event transforms the zoo into a glowing wonderland of millions of lights, seasonal music, and holiday cheer.

One last night in Chicago, evening at leisure.

Day 3: Galena

Continue your Illinois holiday adventure with a heartwarming day of iconic sights, delicious treats, and glowing lights. This morning, venture beyond the city for an overnight of small-town holiday charm in Galena, Illinois, one of the Midwest's most picturesque destinations.

After arriving in the late morning, start exploring the Holidaze Festival, where Galena’s historic Main Street transforms into a winter wonderland filled with twinkling lights, live entertainment, carolers, and local artisan vendors. Browse unique holiday gifts, sample seasonal treats, and soak in the festive spirit of this charming 19th-century town. Enjoy lunch at one of Galena’s cozy cafes or taverns, then spend the afternoon visiting local boutiques, antique stores, and festive pop-ups. Don’t miss the chance to snap a photo with Santa or take a horse-drawn carriage ride through Galena’s scenic streets. As evening arrives, gather for the dazzling Holiday Fire in the Sky, a spectacular fireworks display over the snow-covered hills, lighting the night in brilliant color. Paired with holiday music and warm drinks, it’s the perfect finale for your winter day.

Overnight in Galena, IL (1 Night)

Day 4: Home

After a hearty breakfast, it's time for one last go at any holiday shopping on Galena's Historic Main Street. This is the place to find unique items while savoring a hot cup of your favorite beverage. Stroll the historic district and explore a variety of boutiques, eateries, galleries and local attractions.

After free time, and by mid-afternoon we find ourselves back on the coach heading back to where we first began this fun, educational and productive shopping trip. It's the perfect ride home to check off all the things you had on your list for the holidays. Not only are you bringing back unique gifts, but also bringing back cheerful memories of this holiday adventure in Illinois.

B=Breakfast, L=Lunch