Hurry! Enter Coupon Code XMASRULES to save $50 - offer valid thru 10/28/26. Valid to the first 15 registrants!!

Celebrate the magic of the holiday season with a festive weekend in the heart of downtown Chicago! Begin your adventure with a fascinating guided tour of the historic Macy’s on State Street, where you’ll discover the legacy of Marshall Field’s, admire the stunning architecture, and capture photos of the beautifully decorated holiday windows.

Spend two nights at the elegant Renaissance Chicago Downtown Hotel, perfectly situated along the Chicago Riverwalk and within walking distance of the Magnificent Mile, Millennium Park, the Daley Center, museums, and countless holiday attractions. Your stay also includes admission to the Chicago Architectural Center and a self-guided walking tour, allowing you to explore the city at your own pace.

After dinner, enjoy a spectacular Christmas stage performance of the Christmas Carol before returning to our hotel for the evening.

No holiday visit to Chicago is complete without experiencing the beloved Christkindlmarket. On Friday and Saturday, we’ll have plenty of time to wander through the charming wooden vendor stalls filled with handcrafted gifts, European imports, sparkling ornaments, and seasonal delicacies while the aromas of roasted nuts, pretzels, bratwurst, and warm mulled wine fill the air.

Throughout our time, enjoy your free time shopping along the world-famous Magnificent Mile before concluding the weekend with our train ride back to Milwaukee. I will be available to help direct you throughout our time. Some options to consider include a visit to the beautifully decorated Driehaus Museum, where the opulent Nickerson Mansion is transformed with elegant Christmas trees, seasonal décor, and festive displays that capture the grandeur of a Victorian Christmas. Maybe you would prefer to experience Chicago through its flavors on a delicious Christmas Food Walking Tour featuring festive treats, local favorites, and lunch. Enjoy plenty of free time to shop, sightsee, relax, or take in an optional theater performance.

From historic landmarks and festive markets to holiday entertainment and unforgettable shopping, this getaway is the perfect way to celebrate the season in one of America’s most magical Christmas cities.

This tour includes train transportation, two nights accommodations, $15 daily breakfast voucher, one dinner, Macy’s Historical Tour, Visit to Christkindlmarket, a classic Christmas show, and your Hollitude Representative.