Chicago & Milwaukee Itineraries
Holiday Highlights
Tour Overview: What to Expect
Embrace the festive spirit with a special holiday-themed tour through Chicago and Milwaukee. This 3-day getaway is designed to showcase the holiday magic of both cities. You’ll stay in a comfortable hotel in Chicago for the entire duration of the tour. In Chicago, revel in the glittering lights of the Magnificent Mile and the enchanting Christkindlmarket. On one of the days, we’ll take a delightful day trip just 90 minutes north to Milwaukee, where the holiday cheer continues with a charming European-style market and vibrant neighborhood decorations. Enjoy bright lights, local crafts, and warm, festive treats that bring out the joy of the holidays.
Best of the Midwest
Tour Overview: What to Expect
Discover the heart and soul of the Midwest as you journey through two of its greatest cities: Chicago and Milwaukee. This 3-day getaway perfectly blends cultural richness, historical depth, and culinary delights. Start your adventure in Chicago by exploring the renowned Art Institute, marveling at the architectural wonders of the Loop, and strolling through the vibrant neighborhoods of West Loop and Chinatown. Then, travel just 90 minutes north to Milwaukee, where you’ll tour the historic Pabst Mansion, visit the Harley Davidson Museum, and enjoy the scenic views of Lake Michigan’s waterfront. Our expert guides ensure you experience the most memorable and authentic aspects of each city.
Midwest Hidden Gems
Tour Overview: What to Expect
Uncover the best of the Midwest with our 5-day tour between Chicago, Illinois, and Milwaukee, Wisconsin. Start your adventure in Chicago, where you’ll explore hidden gems like lesser-known museums and cultural centers, and discover the diverse ethnicities that built Chicago through its 77 unique neighborhoods. Visit vibrant communities such as Pilsen, Chinatown, and Greektown, each offering a rich tapestry of history, art, and cuisine. Then, journey just 90 minutes north to Milwaukee, where you’ll experience the local craft beer scene with visits to historic breweries, explore the Milwaukee Art Museum’s unique collections, and enjoy the scenic Lake Michigan waterfront. This tour blends the urban excitement of Chicago with the rich heritage and charm of Milwaukee, showcasing the true hidden gems of the Midwest for an unforgettable experience.
The Merry Midwest Express
Tour Overview: What to Expect
Embark on a heartwarming holiday adventure through the festive cities of the Midwest! Begin your journey in Chicago, where twinkling lights, iconic holiday window displays, and classic seasonal treats create a magical winter wonderland. Then, ride northward to Racine for a Holiday Bakery Bus Tour—a sweet experience featuring local bakeries, kringle tastings, and hometown charm. The holiday cheer continues in Milwaukee, where you’ll spend a full day exploring shimmering light displays, traditional German Christmas markets, and indulgent local fare. From big-city sparkle to small-town sweetness, this getaway is packed with festive fun, nostalgic cheer, and delightful treats around every corner!
Check “Event Planning” Off Your List!
We do not ask for a deposit or signed contract, simply fill out the form below with as many details as possible.
We will contact you to confirm your booking. At this time, we ask you provide your tentative head count so we can confirm reservations with your selected locations.
Five days prior to your tour date we will need a final headcount, list of any allergies or dietary restrictions, and payment via credit card or check.
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