Chicago Itineraries

Windy City Wonderland

Location: Chicago
Duration: 3 or 5 days

Tour Itinerary: What to Expect

Immerse yourself in the festive spirit of Chicago with our ‘Windy City Wonderland’ tour. Spanning either 3 or 5 days, this holiday-themed adventure showcases the city’s dazzling winter lights, bustling markets, and joyous celebrations. Explore iconic locations decked in holiday finery, such as the Magnificent Mile and Millennium Park, and experience unique Chicago traditions and gourmet seasonal delights. Whether you’re marveling at the Christkindlmarket or enjoying a special holiday concert, this tour offers a magical blend of activities that capture the heart and excitement of the season.


Beyond the Skyline

Location: Chicago
Duration: 3 or 5 days

Tour Itinerary: What to Expect

Embark on an unforgettable journey through Chicago’s vibrant history and culture. From iconic architecture and historical landmarks to hidden gems and diverse neighborhoods, this tailored 3 or 5-day tour offers a deep dive into the true spirit of the Windy City. Experience a comprehensive exploration guided by local experts, designed to enrich your understanding and appreciation of Chicago’s unique heritage. Ideal for those seeking an adventure beyond the typical tourist paths.

Simply in need of a Step-on Guide in the Great Lakes Region?

Our tour guides are professionally trained, each with a passion for the city and experience in group travel. Available on an hourly basis, our step-on guides will show off the port cities and sights of the Great Lakes to fit with your itinerary and needs.

Simply in need of a Step-on Guide in the Great Lakes Region?

Our tour guides are professionally trained, each with a passion for the city and experience in group travel. Available on an hourly basis, our step-on guides will show off the port cities and sights of the Great Lakes to fit with your itinerary and needs.

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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