Bike Tours in Chicago

Explorers, Bike Lovers, Friends, Family, and everyday people too! Our bicycle tours are designed for anyone that loves exploring great neighborhoods while hearing interesting stories about the history and culture that make Chicago a world class city. We have so many bike tours to choose from including ones appropriate to explore unique neighborhoods, the foods that made Chicago famous, Chicago nightlife, Chicago’s gangster history, and kid-friendly side to Chicago.

Yes, we provide water on all of our food tours.  And most of our tours involve some sort of beverage, whether it be craft beer or hot tea.

We CAN provide food substitutions for vegetarians on ALL tours. Gluten-free substitutions are available on certain tours.  While we try our very best to accommodate food allergies, we cannot guarantee certain avoidance from various food allergies.  We would encourage you to ask questions along the way and see if our guide might recommend a substitution.

Sorry, we do not allow pets on any of our tours.  Actually, you can bring a goldfish in a plastic bag.  Actually, no don’t bring the goldfish either.

Yes, most of the restaurants we visit will have restrooms to use.  We do recommend using the restroom prior to arrival to your tour, however, to expedite the start of the tour.

We change the tour slightly every six to eight months. Many parts of the tour remain the same, but we do our best to improve upon and enhance the tour. Don’t be embarrassed to come back for more and repeat the experience – many people do!  We had one guest tell us he has taken the same tour 8 different times.  When we mentioned he should look at one of the many other tours we offered, he stated no need.  His reason is every time he takes the same tour he gets a different tour guide and each tour guide provides their own unique spin and presentation style.  So if you come back to the same tour, be prepared for a new and engaging experience each and every time.

Absolutely! Many of our attendees live right here in Chicago or the outlying suburbs. Locals often attend to learn things about the neighborhoods and the city in which they live that they did not know beforehand. We mainly stay off the beaten path, and thus avoid being consumed by crowds. Locals (and those that want to feel like locals) can often get the MOST out of the tours since the tours are designed to show you how the locals live, work, eat, and play in each neighborhood we cover.

We offer pouches on the front of our bikes that allow you to store wallets, cameras, cell phones, and other smaller items, and you are welcome to keep any larger items back at our shop while you are out on a tour or rental.

No bike, no problem! We have hot deluxe comfort bikes for you to ride, and helmets to keep you safe. Each bike is labeled with a name that describes its personality but you can also tell them apart by their distinctive markings and behavior. They each have front pouches and back racks for storage of smaller items. Although we recommend riding our bikes, you can bring your own but we don’t offer any discounts for doing so.  Moreover, due to so many types of bike makes and models, if you bring your own bike and have a mechanical issue it will be unlikely we will have the proper tools to fix the issue.  But we will have the tools to fix any issues that might arise from use of our bikes.  All of our bikes are deluxe comfort bikes with fat tires, cushy seats, and fenders to keep you clean.

You should wear clothes, of course, but beyond that you’re free to show your expressive nature in what you decide to wear.  We recommend you bring small items such as an ID, credit card and cash (to tip the guide), cell phone, and camera.

We suggest tennis shoes and comfortable, loose-fitting clothes that are appropriate for the weather conditions on the day of your tour.  We strongly suggest you wear layers, particularly in spring and fall, as you can always take a layer off if you get too hot or add a layer if you get too cool.  Many of our tours ride close to Lake Michigan, which is one of the largest lakes in the world and can alter the temperature quickly based on the direction of the wind.  We offer pouches on the front of our bikes that allow you to store wallets, cameras, cell phones, and other smaller items, and you are welcome to keep any larger items back at our shop while you are out on a tour or rental.

Bike Tours:18-20 people per tour is the perfect number for most of our bike tours that do not include food.  For our Kid-Friendly tours as well as our Bike & Food Tours, we max out at 15 guests per tour guide.

Our bike and cultural tours have been developed for a wide variety of ages, interests, and skill levels.  But not all tours are appropriate for younger riders. Regarding seniors, we rarely hear that seniors have a hard time on our tours as long as they feel comfortable on a bike.  The Southside Gangster tour is definitely our longest ride and might give the most issues.  And seniors might want to beware of taking the tour in extreme temperatures.  Regarding kids on our tours, not every tour is appropriate for younger riders.  For instance, we do not recommend our Bike & Food tour participants for ages 17 and over due to the fact that we do go into bars in certain neighborhoods and the tour may not be appropriate for them.  That said, we do realize that every child is different so we do leave it in the hands of the parents to ultimately decide what is ok for their child and what is not.  It might be that you just sit outside during the stops that include the bar.  We do encourage younger riders that are under 12 years old to take Bobby’s Tike Hike: Kid’s edition bike tour as well as our Museum & Parks at Sunset Tour (in lieu of the Night Tour).  While many kids can handle our Lakefront Neighborhoods Tour, we have noticed that it’s not appropriate for riders 8 and under who are average riders for their age.  Those kids would want to stick to our Tike Hike or Sunset Tours.  Whether to bring your child is ultimately up to your discretion, but please note that ALL CHILDREN need a paid ticket. Our “under 4” pricing is deeply discounted and usually pays for the special equipment needed for your kids.  A good rule of thumb to know whether a tour is kid-friendly to see if we offer kid prices on the tour.  If no kid prices, it’s probably not the best suited.  But again, it’s up to the parents to ultimately decide because all kids are different.  For food tours, we assume that if your child is below age 3 than they will not be participating in the food tasting portion of the tour or that they might be sharing food with a parent. Therefore, for children below age 3, no ticket is required and there will not be a food portion dedicated to this child. If you’d like food for your child under 3, then please do purchase a ticket in advance. Either way, please indicate when you sign up whether you are bringing a child on the tour so that our tour guide can be prepared.  Please also note that if you are bringing kids on our bike tours, you will need to indicate what additional equipment they will need during your reservation of the tour.  We offer child bikes, tag-alongs, trailers, and child seats.  If your child becomes unruly we would just ask that you step away from the group for a bit to calm your child down before returning to the group.

Enough biking that you’ll see a ton but not more than you can handle! The pace is usually good for everyone.  We’ve rated each tour level so that you can pick the right tour for you. We do stop at various points of interest and attractions so that you can have a brief rest while our tour guides explain the history of Chicago in a way that brings the stories to life.  While you want to make sure the distance we cover is suitable for you, remember that we will never be biking continuously for that amount of time.  We will have 6-8 stops mixed in along the route for resting periods and to learn about Chicago.

Expect the very best.  Our staff takes great pride in being the best in their field.  So we don’t skimp on any of the details.  All of our tours are different and they all go in various directions from downtown.  Our staff has spent a lot of time and energy making sure that we bring the very best of Chicago to you on our tours.  So each route is carefully detailed and every story is crafted to perfection to make sure you come away with the best Chicago experience possible.

“Strenuous” is not in Bobby’s vocabulary.  All of Bobby’s bike tours are set at a relaxed to moderate pace for riders of all skill levels.  In order of “difficulty,” they are as follows:  “Bobby’s Tike Hike: Kid’s Edition” and Bobby’s “Museums & Parks at Sunset Tour” are each a quick two hours covering less than 5 miles, with a brief rest-stop along the way.

Both Bobby’s “Lakefront Neighborhoods Chicago Tour” and “City Lights at Night Chicago Tour” are set at a relaxed pace, covering about 6-8 miles in 3 hours, including a small break at a quiet, outdoor café/beer garden just in case you need a snack (snacks are ala carte and not included in the regular tour price; private groups can include breakfast/lunch/dinner with one of our partners in their package upon request).

Likewise, foodies on Bobby’s “Bikes, Bites & Brews Chicago Food Tours” cover about 12 miles in 4 hours, and there are lots of delicious breaks along the way.   We call it “Somewhat Moderate to Easy.”

Bobby’s “Southside Chicago Gangster Tour” covers 12 miles in 3 and a half hours with a break as well. It’s a bit more moderately paced but not advanced.

Our bike tours are led by experienced Bobby’s Bike Hike tour guides. During our tours you will learn about the history and culture of the various neighborhoods and attractions we visit, as well as get to see Chicago the way Chicagoans experience their City. Bobby’s Bike Hike is one of the oldest City Bike Tour companies in the country, offering quality tours since 2002.  We are proud to have put bike tours on the map in Chicago!  Bobby’s Bike Hike Tours is a mid-sized local tour business that concentrates on details, organization, and accuracy. We will not show you anything unless we know about, believe in it, and love it! We use old school methods, modern technology, and a lot of personality with everything that we do. We focus on good honest food and fun, striving to make sure each person that takes our tours has a memorable Chicago experience.

We provide water free of charge on all of our Bike & Food Tours.  On all other bike tours where food is not offered, we do not provide water but offer it for purchase inside our bike shop where the tour begins.