Inside Chicago Walking Tours is a unique walking tour company founded by an experienced tour guide and product development director for a major sightseeing company in Chicago. Given the freedom to research and construct her own tours, she used her experience as a teacher, writer, improv comedian, and tour guide to create tours that tell the story of Chicago in an engaging, educational, and always entertaining way. Inside Chicago Walking Tours combine architecture, history, and storytelling in one powerful experience of the city that no other tour company can match.Choose to start, finish, or center your holiday on a trip to Inside Chicago Walking Tours by using our Chicago trip builder site.
What makes us different? It's our ability to find the hidden and fascinating details of buildings and areas that people pass through or pass by every day. It's our emphasis on experiencing architecture as an art, appreciating both the exteriors and interiors of Chicago's gorgeous buildings. It's our passion for showing visitors, whether they be out-of-towners or Chicagoans, a side of Chicago that they haven't noticed before: the second side of the Second City.
Tours average 2 hours and run rain or shine. Please refer to the tour offerings on our website for more details.
Create an itinerary including Inside Chicago Walking Tours
Inside Chicago Walking Tours Reviews
Though I live in Chicago, I enjoy playing tourist in my own city. Having lived here most of my life I've seen a lot and gone on plenty of tours. Hillary's The World Within walking tour was really... more »
What a great decision to do a private tour with Hillary - she is a fountain of knowledge! Not only did we learn about the architecture and development of the city, but also she took us inside to see.... more »
Plan your trip to Chicago
Get a personalized planA complete day-by-day itinerary
based on your preferences
Customize itRefine your plan. We'll find the
best routes and schedules
Manage itEverything in one place.
Everyone on the same page.
See all ›
See all ›
See all ›
Hidden gems in Chicago
Side trips from Chicago
Nearby attractions in Chicago
Plans to Inside Chicago Walking Tours by other users
8 days in United States BY A USER FROM UNITED STATES April, popular sights PREFERENCES: April ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Chicago BY A USER FROM CANADA July, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Medium 10 days in United States BY A USER FROM GERMANY October, culture, outdoors, relaxing, historic sites, museums, shopping, slow & easy, popular & hidden gems PREFERENCES: October, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 4 days in Chicago BY A USER FROM UNITED STATES July, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Chicago BY A USER FROM ISRAEL August, culture, historic sites, museums, popular & hidden gems PREFERENCES: August, culture, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES August, kids, outdoors, historic sites, museums, fast-paced, popular sights PREFERENCES: August, kids, outdoors, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Fast-paced