Why Take a Guided Chicago Tour?
Good question! Did you know that the Second City is actually first when it comes to bike riding? Chicago consistently ranks at the top for both walking and biking because it’s flat and easy to access (take that NYC!). Plus, all the neighborhoods, parks, and attractions are connected through a network of sidewalks and trails. So it makes sense that the best way to experience life in Chicago is on two wheels (or two feet) alongside fun folks just like yourself.
And while it’s true that anyone can whizz from place to place in a car, bus, or boat, you miss out on soooo much. With a Chicago bike tour or a Chicago walking tour, or even renting a bike, you can actually hear the roar of Buckingham Fountain, touch the iconic lion statues at the Art Institute, and smell the Chicago-style pizza wafting through the air. Join us for a memorable Chicago tour – whether it’s a walking, bike, or food tour!
But if you do take a guided tour of Chicago, make sure it’s at the beginning of your trip. It’ll really help you become more familiar with the city’s layout and sites. You can navigate the rest of your visit more easily when you understand Chicago’s street plan. Plus, you can circle back to some of the locations or restaurants you want to visit again. We’ve found our tours make a fantastic jumping off point for discovering things to do in Chicago.
Why choose Bobby’s Bike Hike?
Founded in 2002, we were one of the first guided bike touring companies in the country and we consistently rank as the #1 sightseeing tour on Tripadvisor. Why? We’ve combined our knowledge as a second-generation tour operator with our drive and passion for tourism and travel, to create one-of-a-kind Chicago bike tours, Chicago food tours, and Chicago walking tours that speak to a variety of ages, interests, and skill levels.
Plus, our tour guides are some of the most experienced in the business. Tired of listening to a monotone voice drone on and on? Of course you are. That’s why we take extra care to find guides that are personable, knowledgeable and most importantly, FUN.
In addition, our guides take your safety very seriously. They know the sidewalks and pathways inside and out so you’ll always be on the best route. And don’t forget, because Chicago is very flat and well connected geographically, it’s easy for everyone to zip from the Lakefront Trail to neighborhoods to Chicago’s tourist attractions.
What kind of Chicago tours do you offer?
So many! All of our tours provide an insider’s view of the culture, history, architecture, and little-known facts that define this phenomenal city. For example, did you know that Chicago is home to the Twinkie and house music? Well, now you do.
Are you a foodie? Whether you’re craving a local favorite such as a Chicago-style hot dog washed down with a handcrafted beer, or want to explore the city’s unique culinary and ethnic innovations, we have a Chicago food tour that’s perfect for you. So get ready to discover the famous dishes you’ve heard all about as well as delicious hidden gems in off the beaten-path neighborhoods.
Love culture, nature and/or history? Whether you want to explore the Lakefront Trail, visit unique neighborhoods and parks, see Chicago light up at night or learn about infamous Chicago gangsters we’ve got the right tour for you.
Have kids in tow? Great! Although some of our tours are kid-friendly, we created our Tike Hike specifically with families in mind. From a petting zoo, to making wishes in fountains, to rubbing the foot of a GIANT Abe Lincoln, we’ve got plenty of things to do with kids in Chicago that’ll keep everyone entertained.
What if I want to go solo vs. taking a tour?
No prob. If touring isn’t your thing, we offer discounted Chicago bike rentals and have lots of bikes to choose from. Each rental comes with a free lock, helmet, and map. Plus, we’re located right in the middle of the 20-mile Lakefront bike trail, which makes its super easy to get to all the “must-see” attractions, neighborhoods, parks, and beaches!
In town for an event? Bobby’s Bike Hike is proud to partner with Chicago’s Bike the Drive, Lollapalooza, the Chicago Marathon and Triathlon, Chicago’s Critical Mass bike rides, and more to offer discounted rentals while you’re here.
And Chicagoan’s, don’t fret because we’ve got your back, too. Check out our discounted bikes for sale, including used bikes, as well as our bike repair and tune-up services. Our goal is to be the best “go-to bike repair shop” for Chicago’s Lakefront Trail, so please take us for a spin.
The Benefits of Picking Bobby’s Bike Hike for Your Guided Tour of Chicago
When you’ve been around as long as we have, you learn to do things right. We are organized, knowledgeable, safe and most of all — we are entertaining! Booking a tour with Bobby’s Bike Hike ensures you will have a good time, whether you’re a resident who wants to try something new on the weekend or a visitor who only has a limited window to take in the sights.
We know your time is valuable, and we respect that by reminding you our popular tours sell out quickly. When you book a tour in advance online, you secure your spot on your chosen day, and you also get a 10 percent discount from our in-store rate — our way of saying thank you for picking Bobby’s Bike Hike.
Find a tour that matches with your unique interests. We provide many variations to appeal to different people. Foodies, exercise junkies, history nuts — we have tours to please you all. Our dynamic guides present information and fun tidbits even lifelong Chicago residents may not know. Our Chicago guided tours aim to keep you amused and absorbed in everything along the way. We empower our guides to make this tour one you won’t forget.
We Have Earned Accolades From Top Tour Industry Names
- The most organized tour company, according to the Chicago Reader
- The best city tour, according to CitySearch
- Award of Distinction, from Viator
You develop a good reputation like ours by giving people the experience they want, and that’s what you get at Bobby’s Bike Hike. We have even earned notice from Midwest Living, National Geographic and American Airlines magazines, all discerning publications that have written about our tours.
Book Your Guided Tours in Chicago Today
Now that you know what we’re all about, are you ready to explore the city with us? Our guides love helping people taste new foods, learn information, become more comfortable on their bikes and have a great time while they make their way through our beloved city. We can accommodate anyone who wants to try this unique way to see Chicago. Contact us today to book your tour with friends, family or coworkers.