Chicago Step on Guide Service

  • 2 - 8 Hours
  • Walking Tour
  • Private Tour
  • Daily


  • Our local Step-On guide will join you in experiencing diverse neighborhoods of Chicago and iconic architecture!
  • Engage with the Windy City’s rich heritage and modern allure as our expert guides showcase its vibrant culture, from the Loop to Millennium Park!
  • Hear fascinating history of the Chicago River, towering skyscrapers!
  • Uncover the distinctive charm and character of Chicago through tailored storytelling experiences!

Discover the dynamic city of Chicago in a personalized and engaging way with our Step-On tour services. Our expert local guides invite you to explore the diverse neighborhoods, iconic architecture, and vibrant culture that define the Windy City. From the architectural marvels of the Loop to the artistic energy of Millennium Park, our local experts showcase the essence of Chicago’s rich heritage and modern allure.

Immerse yourself in the history of the Chicago River, the stories behind the towering skyscrapers, and the enticing shine of the Magnificent Mile. Whether it’s the deep-dish pizza or the legacy of jazz in Bronzeville, our step-on tours will cater to your interests, offering an unforgettable journey through the heart of Chicago’s distinctive charm and character.

Community Impact

Travel exposes us to new cultures, customs, and experiences, and a private WeVenture tour highlights some of the less-visited Chicago neighborhoods and supports these communities in a way that other tours are unable to when limited to the city’s usual tourist destinations.

This tour opens up the potential to not only support more areas of the city and help us play a bigger role in the diversification of experiences Chicago has to offer but also allows our guests to see how and where everyday residents of Chicago live and work.

By promoting diversity and encouraging cultural exchange, our tours lessen the divide in the segregation of Chicago and invite our guests to explore uniqueness in the neighborhoods they might not find on their own. As a result, this fosters a sense of community and helps to create a positive image of Chicago.

WeVenture tours are designed to support small businesses and provide them exposure to a wider audience. By fostering a sense of community where the respect is mutual and the relationship is symbiotic, we help drive revenue to the local vendors who we know and love in Chicago.

Price Includes

Price Excludes

  • Local English-speaking guide
  • Souvenirs
  • Guide gratuity
  • Additional food & drink


Walking Tour

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