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

  Steve was amazing. Very personable and knowledge about all things Chicago. We did the street art and west side tour 1/2 day tour. We ended up riding... read more about 9 miles and he offered to extend it, but we had a prior dinner engagement. He even sent a detailed map of our tour plus some excellent photos he took along the way. Highly recommend!

  I spent an amazing 4.5 hours riding 15 miles on a totally customized bike tour with Steve. He knows so much about the art, architecture, and history along the way... read more (he is a retired teacher so it's not surprising.) After I got home he even provided me with a detailed map of the ride that included photos of me along the way with informational links about the scene shown. A+ experience.

  Steve created a wonderful memory for us while on a short trip to Chicago. Our group of girls had a mix of biking experience and he went out of his... read more way to ensure we all felt comfortable. This tour was a comfortable pace filled with local art and history of each space. The ability to ride through the city made us feel like a local even though my riding skills may have indicated otherwise. Thank you Steve for making us feel like a priority to you and your city. Would love to come and do this again.

  A fantastic bike tour, personally tailored to your interests. We did a 3-hour ride with a group of four who signed up together, but you can also sign up alone... read more and be paired with others.

Steve is a friendly and knowledgeable guide. We had a rider who hadn't ridden a bicycle in years and Steve's loaner bike and helmet worked out great.

Highly recommend the "bike the boulevards" route and on through Pilsen and Chinatown. Great history and architecture.

Thanks, Steve!

  Steve is great and love the tours. My wife took me on one a couple years ago and we went again while some friends were in town last week. Great... read more way to see the city and each tour is customized based on what you are interested in learning about and how far you want to go. Highly recommend!

  Absolutely loved this bike tour with Steve. Our tour was customized to what we wanted to see. Steve included stops in between our requested stops so we could learn and... read more enjoy more about this beautiful city. Steve was patient with us and accommodating to our level of bike riding, making sure we were following behind and letting us know our route ahead. Steve took pictures and put them together on a map showing where we had been. He also included photos from the movie sites we stopped at so we could compare our pictures with the movie. It was awesome! I will recommend Steve to friends and book again!!!

  If you want to get to know Chicago more personally, try this out. This was one of my favorite experiences during my three day stay at Chicago. I did all... read more the tourist must-dos but it was nice to bike around neighborhoods and to feel what exactly the locals see everyday. Steve was great with everything from picking out/adjusting a bike for my size to explaining fun little details of Chicago. If you love being active and want a new experience while traveling, this would be great for you.

  This was by far the best day of my vacation in Chicago. A bike tour is the best way to see a city, and Steve's street art bike tour was... read more such a great experience. We saw great popular murals and tons of never seen or known about before. Steve knew the answers to all my questions about the artists, the collaborations, the backgrounds of the pieces and more. On top of that I felt very safe the whole and trusted his urban biking skills. It was truly a memorable experience and I can't wait to take my friends with me next time I go!

  My friend from out of town wanted to visit me in Chicago for my birthday. Instead of going out to a fancy dinner, we decided to go on an... read more adventure with Chicago Bike Adventures. It was a great! I live in Chicago and love to bike. I wasn't sure if I would see anything new or unexpected on my trip because I live here, but I certainly did! Steve is extremely knowledgeable and knows about all the hidden gems! He customized the tour for just me and my friend and one other woman that joined us that day. It was great to be able to see all of the things I wanted to see (like street art, history, and planning stuff) and not get into the things I didn't care as much about. I'm sure there are many more customized adventures that he is prepared to give!

We saw a lot of really fantastic street art. We also stopped by a brewery in Pilsen, Lo Rez. I highly recommend it! Steve was extremely knowledgeable about all of the things and places we visited. He was also very approachable and fun to ride with. He even lent someone a pair of socks so she could be a little warmer on the ride. Great guy.

It was great how Steve knew which route to take. He clearly did a lot of research in finding the best way to get around. I ride my bike in Chicago so I know how difficult it can be getting around if you don't find a bike lane, or a less busy street. The ride that day was very pleasant and stress free.

Oh! I should mention that it was 33 degrees when we did this trip and I still loved it! We bundled up and kept warm by moving.

I would definitely recommend this for a visitor or a local!