Chicago Multi-Day Trip Itineraries
Chicago at Christmastime
Tour Itinerary: What to Expect
Experience the magic of Chicago during the holiday season with a festive getaway featuring iconic landmarks, holiday markets, and seasonal treats. Explore the city’s diverse neighborhoods on a guided tour, enjoy skyline views, and savor authentic Italian cuisine in Little Italy. Discover the Museum of Science and Industry’s Christmas Around the World display, enjoy lunch beneath the towering Christmas tree in Macy’s Walnut Room, and browse the Christkindlmarket. Sample holiday treats on a Christmas Bakery Bus Tour and enjoy lunch in Greektown.
Chicago Hub & Spoke: Milwaukee & Route 66 Highlights
Tour Itinerary: What to Expect
Explore Chicago and beyond while staying at one downtown hotel. Discover Chicago’s iconic landmarks and enjoy an authentic Italian dinner in Little Italy with a pasta-making demonstration. Travel to Milwaukee for a guided city tour featuring the Harley-Davidson Museum, Pabst Mansion, Milwaukee Art Museum, and an authentic German lunch at Mader’s Restaurant. Then, journey along historic Route 66 in Illinois, visiting Joliet Prison, the Jacob Henry Mansion, classic roadside attractions, and the famous Gemini Giant.
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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