Chicago Walking Tours
Bobby’s Bike Hike offers Chicago’s top-rated walking tours designed to help you better orientate yourself, learn interesting stories, and meet amazing folks from all over the globe. Our entertaining guides set the standard and make sure your experience is top notch.
- 11:30am Daily
Taste your way through Chicago's most famous recipes on this relaxing and fun walking food tour. In an exciting two and a half hours, you'll feast on Chicago culinary legends such as deep dish pizza, locally crafted beer, a Chicago-style hot dog, and the...Learn MoreGiordano’s Lake StreetLearn MoreSCHEDULE11:30am DailyLEVELTotally WalkableDURATION2.5 hoursLENGTH1.25 milesPRICE
(includes Food & Beverage Samples)
Students/Military/Seniors: $45.75Adult$48.75Student / Military$43.75Students / Seniors 65+Kids under 12Kids under 4HighlightsChicago Loop
Chicago Style Deep Dish Pizza
Famous Chicago-mix popcorn
Locally Crafted Beer
Chicago-style Hot Dog
State Street (that Great Street)
The Art Institute
the start of Route 66
The Original BrownieCustom Line11:30am DailyMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at: $45.75Gift Certificates
- 4pm Friday & Saturday
Curious about Chinatown but unsure where to start? Let our Bobby's Bike Hike Chinatown Food and Culture Walking Tour be your guide! Chicago's Chinatown, located next door to the Loop on Cermak Street and Wentworth Avenue, bursts with colorful shops, impr...Learn MorePui Tak CenterLearn MoreSCHEDULE4pm Fri & SatLEVELVery EasyDURATION2.5 hrsLENGTH1 milePRICE
(includes Food & Beverage Samples)
Kids (under 4): $10.75Adult$48.75Student / Military$43.75Students / Seniors 65+$43.75Kids under 12Kids under 4HighlightsWentworth Avenue
Dim Sum Treats
Lamb & Cumin Sandwich
Chinese Cultural Institution
Beijing DuckCustom Line4pm Friday & SaturdayMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chinatown-Chicago-Culture-and-Food-Tour.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at $43.75Gift Certificates
- 2:30pm Saturdays
No matter the season, the weather, or the political climate, The Windy City has two unparalleled passions: beer and improv comedy. For over a century, Chicago has been churning out some of America's all-time favorite comics and brews. Join Bobby's...Learn MoreSecond City – Old TownLearn MoreSCHEDULE2:30pm SaturdaysLEVELEasyDURATION2.5 hoursLENGTH1 milePRICE
(includes Beer & Snack Samples)
Adults (21+ Only): $60.75
Adult$60.00Student / MilitaryStudents / Seniors 65+Kids under 12Kids under 4HighlightsAmazing Neighborhoods
Well-known Chicago hangouts
India Pale Ales
Belgium BlondsCustom Line2:30pm SaturdaysReserve NowMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2018/03/OldTown.jpgBottom Link -1Bottom Link -2Private Group RequestPRICEStarting at $60.75Gift Certificates
- Private Groups Only
Our private walking tour is the perfect way to learn all about the history and breathtaking infrastructure of the Chicago River! Explore the rolling promenades, historic landmarks, and relaxing mini-parks that frame the legendary waterway. One of our enthusiastic and in...Learn MoreLearn MoreSCHEDULEPrivate Groups OnlyLEVELEasyDURATION1.5 hoursLENGTH1 milePRICE
Kids (under 12): $15.00
Kids (under 4): $5.00Adult$25.00Student / Military$20.00Students / Seniors 65+$20.00Kids under 12Kids under 4HighlightsChicago Riverwalk
Vietnam Memorial & Park
McCormick Bridge house and River Museum
Centennial Fountain & Water Arc
Chicago’s LakefrontCustom LinePrivate Groups OnlyMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-River-walking-tour.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at $15Gift Certificates
- Private Groups Only
Our incredible dessert-and-beverage walking tour is the perfect way to experience everything sweet about Chicago! You'll learn all about Chicago's rich dessert history and taste some of the finest flavors that the Windy City has to offer. Our Sweets &...Learn MoreChicago Cultural CenterLearn MoreSCHEDULEPrivate Groups OnlyLEVELEasyDURATION2.5 hoursLENGTH1 milePRICE
(includes Food & Beverage Samples)
Students/Military/Seniors: $45.75Adult$50.75Student / Military$45.75Students / Seniors 65+$45.75Kids under 12Kids under 4HighlightsMichigan Avenue
River North Nightlife
Dylan’s Candy Store
Fun, Fun, FunCustom LinePrivate Groups OnlyReserve NowMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpgBottom Link -1Bottom Link -2Private Group RequestPRICEStarting at: $45.75Gift Certificates
Enjoy Walking Tours of Chicago With Bobby’s Bike Hike
Chicago is a city unlike any other. The energy, the sights, the people, the river, the food, the history — it all adds up to a vibrant town you’ll want to learn more about as soon as you arrive. Seeing Chicago from the ground level, on the streets where people live and work, will help you develop a true appreciation of this unique place.
Bobby’s Bike Hike offers Chicago’s top-rated walking tours, designed to help you better orientate yourself, learn exciting stories, and meet amazing folks from all over the globe. Our entertaining guides set the standard and make sure your experience is top notch.
Why book a Chicago Walking Tour?
Bobby’s Bike Hike offers a wide variety of award-winning Chicago city walking tours and consistently ranks as having the top tours in Chicago. Plus, we’re proud to be Chicago’s largest and most popular walking tour company, offering new and unique tours each and every year.
Why are walking tours so popular in Chicago? Good question. And we have the answer. Chicago is consistently ranked one of the country’s top walkable cities because of its flat terrain, ease of use, and abundance of wide sidewalks and pathways. You can safely and easily walk anywhere in Chicago without fear of fatigue, and many of Chicago’s top activities and attractions are within relatively close walking distance of each other. Plus, to top it off residents of Chicago are incredibly friendly. Midwestern charm is real, folks, and you can witness it first hand as we walk through this amazing City.
People love the interactive aspect of Chicago walking tours. You can engage all five senses when you use your feet to get around this vibrant city. Inhale the alluring smells of our town’s signature pizza and ethnic food — and taste those delights on our Chicago foodie tour. Watch the hustle and bustle of the crowds moving down the street alongside you. Hear our engaging guides explain the importance of the places you visit, and feel the vigor of a brisk walk or bike ride.
We offer a wide range of walking tours that will appeal to a variety of ages and interests. Whether you want to learn about Chicago history, culture, or fun facts. Or maybe you’re craving an opportunity to taste your way through Chicago, by sampling some delectable ethnic dishes, or devouring Chicago-style pizza and other famous local favorites, or maybe even discovering Chicago’s rich beer history while even sampling a few, we most definitely have a tour catered to your style.
Just keep in mind, whatever tour you decide to take, make sure to reserve your experience on the front end of your trip so we can give you the insight and know how to enjoy everything there is to do in this great City.
Who Goes on Our Walking Tours of Chicago?
Virtually anyone will love taking our tours. Have you recently moved to Chicago? Are you visiting on business or with your family? Do you have friends in town and want to entertain them? We welcome anyone with a curiosity about the city.
Treat Yourself to a Walking Food Tour of Chicago
Our foodie tours provide opportunities you won’t find elsewhere. We have a long history in the city, and we have developed relationships with many of the top restaurateurs and chefs here. On our food tours, you can indulge in samples from Chicago’s top restaurants, without having to wait in line or book a reservation months in advance. We eliminate all that fuss so you can taste Chicago’s most delectable treats with ease.
What can I expect on your Walking Tours?
We consider ourselves to be Chicago’s walking tour experts. So prepare yourselves to be entertained, informed, and we’ll throw in a whole lot of fun as well. Whether you want to sample your way through Chicago’s restaurant scene, explore one of Chicago’s many ethnic neighborhoods, tap into local nightlife, visit famous gangster haunts or experience the joy of kid-friendly fun, we have a tour that speaks to you.
Walking tours allow you to indulge and fully experience Chicago in a very intimate way, utilizing all five senses. Don’t worry, our tour guides won’t ramble on a scripted narration while you sit idly by, like you get on a boat tour or bus tour. You’ll be actively involved and come away with a much greater appreciation for Chicago and the various people, places, and activities that make this City so darn great.
Our tour guides are the best in the business without a doubt, having propelled us to a #1 Walking Tour ranking on TripAdvisor for the past 10 years. We consistently offer tours that bring Chicago history, food, and culture to life. A walking tour of Chicago with Bobby’s Bike Hike will truly be a moving experience that you and your friends and family will enjoy for years to come.
Who would enjoy a Chicago Walking Tour?
Are you coordinated enough to walk and chew gum at the same time? If the answer is ‘yes’, then your already a step ahead of us. All kidding aside, our tours are quite easy for all ages and fitness levels. Luckily, Chicago makes it easy as it provides flat terrain, wide sidewalks, and attractions within close proximity. And if you cannot walk or if you need ADA accessibility, we’ve got your back as well. Most of our tour routes and restaurants are ADA accessible and we do rent strollers for families needing help for their young.
We offer a wide variety of tours, so plenty of options to choose from. And we take extra special care in making sure our routes are perfect so that you experience the very best of Chicago. And while our guides are quite knowledgeable, they are also equally fun. So bring a sense of humor as we explore Chicago the way most Chicagoans enjoy their City, by walking.
What types of Walking Tours do you offer?
Bobby’s Bike Hike leads cultural and historic walking tours that are the finest, most comprehensive, and thought-provoking walking tours in Chicago. Did you know Chicago is home to the original starting point of the famous Route 66? Or did you know Chicago invented the Skyscraper? What about the fact that Chicago successfully reversed the flow of its River? It did! Whether you’re looking for history, culture, food, or just to be entertained by one of our award-winning tour guides, we know you’ll come away with a lasting Chicago experience.
This tour allows you to witness Chicago’s transformation from a dormant industrial-era dock into a thriving post-industrial public space, and the new Riverwalk has won numerous design awards and has done amazing things to activate the Chicago River.
Explore Chicago’s iconic loop. This tour offers a delight for those craving the very foods that Chicago is famous for, including samples of Chicago-style pizza and hot dogs as well as the original brownie and locally-crafted beer.
Chinatown offers a unique opportunity to sample the many diverse and mouth-watering regions of China, without leaving the City. Chicago is home to a large Chinese population and we’ll explore the best of the best of Chinese history, culture, and cuisine. With this Food Tour, you’ll get an inside look at all the delectable options Chinatown has to offer.
Our Craft Beer walking tour allows you to learn about Chicago’s rich beer history, sample some of our favorite local flavors, and learn a little history and culture to boot. It will be impossible to leave this tour without a smile on your face.
And we even offer specialty tours around the holidays, including Bobby’s Holiday Hike: Season Sampling Food Tour from Thanksgiving to Christmas, allowing you to learn about the various foods and diverse traditions that make Chicago so amazing.
Choose Bobby’s Bike Hike for an Unforgettable Walking Tour of Chicago
We know you have other choices for walking tours in Chicago. Why pick Bobby’s Bike Hike? We offer many things that set us apart, including:
- Experience: We are the nation’s longest-running city bike tour company. We have been guiding people around Chicago so long, we’ve perfected the art of hiring smart, dynamic people to conduct our tours.
- Safety: We emphasize safety on every tour we give. We want you to enjoy yourself, but we also want to ensure you do it safely.
- Reputation: People love our Chicago walking food tours so much, they take the time to rate us online. We have been TripAdvisor’s top-rated tour company in the city for more than 10 years.
We tell our tour guides they are true ambassadors of Chicago, and they thrive in that role. With them at the helm, you will explore the real Chicago, a place we are all so proud to call home. See why with an insider’s view of the city. Contact us today to book a Chicago food walking tour that will make your taste buds, brain and legs happy.