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Private Chicago Tours

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Updated: November 17, 2025
 By Canden

We also offer our guiding services for private groups, families, or school groups where we can guide you in the Loop, the South Side and anywhere else in Chicago.

Contact us with the size of your group and what you would like to see and when and we will get back to you with a timely quote.  We employ only the best and brightest tour guides in the city.  Read our reviews here.


VISITING CHICAGO THIS WINTER? Book a private tour for groups of 5 or less at discounted rate. If you have a larger group, need a custom tour, or want a tour at a different time of year, please fill our the request form below.


2-Hour Private Chicago Tours

We understand that our group tours are not for everyone, or that maybe you and your party prefer a more intimate tour that allows for more guide time — for questions, for pictures, whatever!

We offer private versions of our most popular tours:

  • The Birth of the Skyscraper: Architecture Tour is a great way to discover and appreciate the incredible landscape of buildings in Chicago and it ends in Grant Park near the famed Buckingham Fountain.
  • The Riverwalk and Chicago History Tour follows the path of the Chicago River and focuses on the history of Chicago, the Chicago Flag, and the beautiful buildings that line the river.
  • Downtown Loop and Millennium Park Tour, which covers a great portion of Chicago’s downtown Loop neighborhood, public art, and ends in Millennium Park.
  • Our Chicago Ghost Tour -Haunting History is for folks who love haunting history and creepy tales of the dark side of the White City.
  • On The Magnificent Mile Tour, you will discover fun Chicago facts like the history of deep dish pizza while exploring our most popular downtown area.
  • Explore Lincoln Park on our Lincoln Park and Gangster Tour to appreciate a unique neighborhood scattered with hidden history including tales of Chicago Gangsters.
  • We also offer a West Loop tour which combines great storytelling for history buffs with great photo ops for those more in the “sightseeing” mood! 

Private tours start at $325 for a 2 hour tour. Discount rates or corporate rates may apply.

Private Tour Request

Additional Private Tour Options

Our private tours are not limited to our public tour selection. We are also available for custom guided service for wherever you want to go and however long you would like a guide for. We're with you every step of the way from planning to the tour's finish. We base our pricing on the above mentioned tours.


Student Tours of Chicago

Why choose us for your class trip to the Windy City?

  • Because we are fun. We employ only the best, brightest and most energetic tour guides in the city. Our guides are young and young at heart, so your students will relate to them better and vice versa.
  • Because we are affordable. Save your students hundreds of dollars each. We have extensive experience with every aspect of a class trip, including hotel, theater, and restaurant bookings as well as organizing transportation and travel insurance. Save the commission the school tour operators build into their prices.
  • Because we are national. We run tours in Washington DC, New York City, Philadelphia, Charleston, New Orleans, and Boston. We can be your guides on multi-city class trips. We have a trans-city perspective and always tie together things your students have and will experience(d).
  • Because we are personal. Since we are a small company, and we only book one group at a time, your group will get the extra special attention you won't get from the larger companies.
  • Because we are experienced. We're amongst the highest rated tour companies on TripAdvisor for a reason - we're great at what we do! 

And much, much more

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