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See Chicago better than a local

Half- or full-day private tour

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11 or fewer guests

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Customized for food, photos, your interests

Fun modes of transportation

In-person private group tours

Customized for Your Group

Explore Chicago on a fun and flexible custom private group tour. Families, friends, or company outings with 11 or fewer guests will see Chicago from a new perspective with us.

On the day of your tour, the guide meets you and surveys the group to choose the topics and activities to include. We’ll also want to know if you are open to taking a jaunt on a ride share, bike rental, or CTA train or bus. Then on the spot, they customize the tour route and build a unique itinerary for your group!

This private tour makes planning easy for you, so you don’t have to stress around navigating everyone’s various needs. 

We’ll be your Chicago expert on history, architecture, food, drinks and things to do. Our passionate and professional tour guides have gotten us voted for the last two years as “Best Tour of Chicago.”

Sightsee the highlights of downtown Chicago or visit our diverse neighborhoods on this one-of-a-kind private tour. 


  • Nibble on apps at a hip or historic restaurant.
  • Learn about famous skyscrapers and overlooked architectural gems.
  • Get a drink in a neighborhood dive bar.
  • Step into glitzy lobbies in the Financial District.
  • Snap iconic photos of the skyline or street art.
  • Take a coffee break and people watch on the Riverwalk
  • Ride the ‘L’ train loop and gaze at skyscrapers.
  • Shop for locally made artisan foods and gifts.
  • Stroll from Wicker Park to Logan Square on the 606 elevated greenway.
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  1. Choose a half- or full-day custom private tour.
  2. Book the tour with your date, duration, and meeting spot.
  3. The group meets the guide and shares their interests.
  4. Are you open to walking, taking a ride share, the CTA or biking?
  5. Guide drafts your private tour itinerary on-the-fly.
  6. See Chicago from a new perspective and switch gears at any time!

why chicago detours?

Our team of expert tour guides know how to curate a killer experience. We’ve been top-rated since 2010 on TripAdvisor and Yelp.

We have hosted more than 1,200 small groups on private tours. We love to bring curious people to explore stories and places even locals don’t know of Chicago history, architecture and culture.  

So much yummy food and a grand way to spend time with friends!
A whole new way of looking at the city!
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Alex Bean

"I love showing how buildings are physical remnants of history that let us in the present have a glimpse into the past. Sharing where local foods, like deep dish pizza, were first created is a treat to me. I live near the lakefront in Lincoln Park."

Amanda Scortese

"I am fascinated with how and why neighborhoods change, and I love getting people to understand the built world around them. I can take you to the best spots for pastries or hot chocolate. I live on the Northwest Side in the Avondale neighborhood."

Marie Rowley

"I love sharing stories of all the diverse people from Chicago history who really should be in our history books. As your tour guide, I'll take you out for Polish pierogi or Filipino adobo, and I can show you Ravenswood and Lincoln Square like nobody else."

curious about a private tour?