Chicago & Milwaukee Multi-Day Trip Itineraries

Best of the Midwest

Best of the Midwest: Chicago & Milwaukee

Location: Chicago & Milwaukee
Duration: 4 days

Tour Overview: What to Expect

Discover the best of the Midwest on a four-day getaway exploring Chicago’s iconic landmarks and Milwaukee’s rich cultural heritage. Enjoy guided city tours, an authentic Italian dinner with a pasta-making demonstration, and an immersive experience in Chicago’s historic Polish Village featuring a Polish museum, traditional cuisine, and a local bakery. Travel to Milwaukee for a guided tour of its famous landmarks, including the Pabst Mansion and Milwaukee Art Museum, followed by an authentic German lunch at Mader’s Restaurant. Back in Chicago, cruise the river to admire its renowned architecture, explore Millennium Park, enjoy deep-dish pizza, take in skyline views, and shop along the Magnificent Mile.

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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