I found Steve of Chicago Bike Adventures on Trip Advisor. They also have a website: https://chicagobikeadventures.com/about/
I wanted to enhance a four day holiday in Chicago... read more with something more interesting than the usual Red Bus or Architectural River Tours which, while worth doing, are things I had done before. Steve's tours involve riding cycles around the northern neighborhoods of the city for 5 hours while he explained the sights. Before the tour, you are sent a questionnaire which asks about your size, bike riding expertise, and interests: History, architecture, sports, churches, etc.
I chose a cold day in December and was the only person on the tour which meant I got Steve all to myself. When I arrived a the beginning of the tour, Steve was waiting with a helmet and a well tuned bicycle adjusted for my size and ready to go.
We started with a tour of the immediate neighborhood. As we rode He explained the local history and pointed out landmarks. The pace was just right, we kept moving to stay warm, it was about 30 degrees F, with stops at various points of interest. Steve teaches in the Chicago schools when he is not giving bicycle tours and we got along famously. As the tour went open we explored the University of Illinois, street art, the trendy new neighborhoods that are attracting tech workers and historical sights going back 100 years.
One of the best things about a small group tour is the ability to get to know a local, ask questions and get a sense of what it is like to live in the city you are visiting. This is much better than hearing a recording of the points of interest as you drive by on a bus filled with other tourists.
Later Steve took me to a local taco place for lunch. The food was very tasty and we continued our discussion of Chicago, one of the most interesting cities I know.
After 5 hours and 12 miles of bike riding I was tired and very happy to have taken the tour. I suspect you will be just as satisfied if you take one of Steve's bike tours. Although the route is chosen carefully to minimize congested streets, you will be riding in a big city for hours so you should be comfortable riding a bicycle in traffic.
John Kelly
