Bike Tours in Chicago
Bobby’s Bike Hike is the longest running City bike tour company in the country, offering award-winning tours for a variety of ages, interests, and skill levels. Our entertaining guides will take you to Chicago’s most popular neighborhoods and parks, as well as Chicago’s top attractions.
- 9:30am Daily (added 6:00pm Sunset Tour in Summer)
Experience our "Chicago 101" tour which offers you all of the City's most popular attractions rolled into one memorable activi...Learn MoreBobby’s Bike HikeLearn MoreSCHEDULE9:30am Daily (added 6:00pm Sunset Tour in Summer)LEVELEasyDURATION2.5 hoursLENGTH6 mi / 10kmPRICE
Kids (under 12): $25.75
Kids (under 4): $13.75Adult$42.75Student / Military$37.75Students / Seniors 65+$27.75Kids under 12$25.75Kids under 4$13.75HighlightsMuseum Campus
Amazing SunsetsCustom Line9:30am Daily (added 6:00pm Sunset Tour in Summer)Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Museums-Parks-at-Sunset.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at $25.75Gift Certificates
- 1pm Daily (added 10:30am & 2:30pm Weekends)
Rated the best Chicago sightseeing tour of 2017 by TripAdvisor, Most Organized Bike Ride of Chicago by the Chicago Reader, and Best Chicago Tour by Citysearch! This q...Learn MoreBobby’s Bike HikeLearn MoreSCHEDULE1pm Daily (added 10:30am & 2:30pm Weekends)LEVELRidiculously EasyDURATION3 hoursLENGTH7 mi/11 kmPRICE
Kids (under 12): $25.75
Kids (under 4): $13.75Adult$42.75Student / MilitaryStudentStudents / Seniors 65+StudentsKids under 12$25.75Kids under 4$13.75HighlightsGold Coast Mansions
Old Town Historic District
Lincoln Park Zoo
North Avenue Beach
St. Michael’s Church
Oprah’s Old Chicago home
Chicago LakefrontMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Lakefront-Neighborhoods.jpgBottom Link -1Bottom Link -2Custom Line1pm Daily (added 10:30am & 2:30pm Weekends)Reserve NowPrivate Group RequestPRICEStarting from $25.75Gift Certificates
- 11:30am Mon-Sat / 12:30pm Sunday
Working up an appetite won't be a problem on this tour! We'll be sampling from each of Chicago's four favorite food groups - pizza, hot d...Learn MoreBobby’s Bike HikeLearn MoreSCHEDULE11:30am Mon-Sat / 12:30pm SundayLEVELSomewhat Easy/ModerateDURATION4 hoursLENGTH13mi / 21kmPRICE
Students/Military/Senior: $64.75Adult$69.75Student / Military$64.75Students / Seniors 65+$64.75Kids under 12Kids under 4HighlightsGold Coast
Chicago Style Pizza
Chicago-style Hot Dog
Locally Crafted Beer
Amazing LakefrontCustom Line11:30am Mon-Sat / 12:30pm SundayReserve NowMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrewsSignature.jpgBottom Link -1Bottom Link -2Private Group RequestPRICEStarting at $64.75Gift Certificates
- 7:30pm Nightly
Our nighttime Chicago electric bike tour is a party on wheels! Roll through the Windy City on two-wheels with ease, and see some of our most beautiful landmarks lit up a...Learn MoreBobby’s Bike HikeLearn MoreSCHEDULE7:30pm NightlyLEVELE-E-EasyDURATION3 hoursLENGTH8 mi/13 kmPRICE
(Includes Electric Bike)
Students (16+)/Military/Seniors: $47.75Adult$59.75Student / MilitaryStudents / Seniors 65+Kids under 12Kids under 4HighlightsElectric Bikes
Oak Street Beach
Rush Street Nightlife
Cloud Gate at Night
Chicago Lakefront & FireworksCustom Line7:30pm NightlyMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/City-Lights-at-Night-walking-tour.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at $47.75Gift Certificates
- 12:30pm Fri-Sat / 11:30am Sunday
Hop on two wheels and discover a whole new side of Chicago dining! Taste your way through diverse neighborhoods as we explore Chicago's...Learn MoreBobby’s Bike HikeLearn MoreSCHEDULE12:30pm Fri-Sat / 11:30am SundayLEVELSomewhat Easy/ModerateDURATION4 hoursLENGTH12mi / 20kmPRICE
Students/Military/Senior: $64.75Adult$69.75Student / Military$64.75Students / Seniors 65+$64.75Kids under 12Kids under 4HighlightsFulton Market
Rick Bayless Cruz Blanca
World Famous Pierogis
Jeff Mauro's (Food Network) unique sandwiches
Bucktown & 606 Bike Trail
Locally Crafted Beer
The ‘Chicago Handshake’
Chicago Lakefront TrailCustom Line12:30pm Fri-Sat / 11:30am SundayMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrews-Foodie.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at $64.75Gift Certificates
- 9:00am Friday, Saturday & Sunday
Bobby's Bike Hike is rolling out the best Chicago mafia tour every weekend of the summer! This electric bicycle tour of Old Chicago will introduce you to the ...Learn MoreBobby’s Bike HikeLearn MoreSCHEDULE9:00am Fri, Sat & SunLEVELModerate/IntermediateDURATION4 hoursLENGTH16mi/26kmPRICE
Students(16+)/Military/Seniors: $47.75Adult$52.75Student / Military$47.75Students / Seniors 65+$47.75Kids under 12Kids under 4HighlightsBridgeport
Old Palmisano Park
Old Italian Outfit hangouts
Prairie Ave District
Levee Red Light District
Italian Beef Sandwich
Chicago LakefrontCustom Line9:00am Friday, Saturday & SundayMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Southside-Gangster.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at $47.75Gift Certificates
- 3:00 pm Daily (May 1 - September 17)
This tour was designed with your family in mind! Sometimes known as "Bobby's Adventure Series" or "The Best Thing to Do in Chicago with...Learn MoreBobby’s Bike HikeLearn MoreSCHEDULE3:00pm Daily, May 1 - September 17LEVELEasy, Easy, EasyDURATION2 hoursLENGTH4.5 milesPRICE
Kids (under 12): $10.75
Kids (under 4): FREEAdult$34.75Student / MilitaryStudents / Seniors 65+$27.75Kids under 12$19.50Kids under 4$9.75HighlightsLincoln Park Zoo
Oak Street Beach
Peggy Notebaert Nature Museum
Abe Lincoln Stature
Secret GardenCustom Line3:00 pm Daily (May 1 - September 17)Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Tike-Hike-KidsEdition.jpgBottom Link -1Bottom Link -2Reserve NowPrivate Group RequestPRICEStarting at $10.75. Kid's under 4 FREEGift Certificates
Why book a bike tour through Chicago?
Bobby’s Bike Hike offers a wide variety of award-winning Chicago city bike tours and consistently ranks as having the top tours in Chicago. Plus, we’re proud to be one of the country’s longest running city bicycle tour companies.
Why are bike tours so popular in Chicago? Good Question. And we have the answer. Chicago is consistently ranked the #1 City for bicycling in the country because of its flat terrain, ease of use, miles of bike lane and extensive trail systems. You can safely and easily ride anywhere in Chicago, and bike trails connect the neighborhoods to the parks, beaches, and Chicago’s top attractions. Plus, to top it off residents of Chicago are incredibly bike-friendly. Midwestern charm is real folks, and you can witness it first hand as we cruise through this amazing City.
What can I expect on a Bobby’s Bike Hike bike tour?
We consider ourselves to be America’s Bike 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 Chicago’s culinary delights, discover one-of-a-kind neighborhoods and parks, tap into local nightlife, visit famous gangster haunts or experience the joy of kid-friendly fun, we have a tour that speaks to you. You can cover much more ground than a Chicago walking tour, plus you can get more up close and personal to Chicago attractions and neighborhoods than you can when sitting idle and being narrated to on a Chicago bus or boat tour. We encourage you to experience Chicago through all five senses.
Our tour guides are top notch, having propelled us to a #1 Ranking on Tripadvisor for the past 10 years. We consistently offer tours that bring Chicago history, food, and culture to life. A bike 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 Bicycle Tour?
Ever heard the phrase “It’s as easy as riding a bike?” Well, it’s just that easy. On a majority of our tours at least. While most of our tours are set at a relaxed pace, Bobby’s Bike Hike offers Chicago guided bicycle tours that are rated from kindergarten easy to advanced, so you can pick the bicycle tour appropriate for you. We offer tours of Chicago for a wide variety of audiences, ages, and skill levels. So as long as you can ride a bike, you’re ok to ride with us. And we even offer tandems, child bikes and equipment for those riders who might need additional assistance.
What types of bike tours do you offer?
We offer Chicago bike tours that cater to a variety of ages, interests and skill levels:
The Lakefront Neighborhoods Tour, which is our most popular and longest running tour, takes you out of the tourist beat and into the upscale neighborhoods, quiet parks, and Lakefront Trail where you can experience life like a Chicagoan.
Our Museums & Parks Bicycle Tour is our “Chicago’s Greatest Hits” tour as it hits all of Chicago’s top attractions, all within an easy 2.5 hour ride. This tour is great for everyone, including even younger riders, offering stunning views of the magnificent Chicago skyline as well as Grant Park, Museum Campus, Navy Pier, Millennium Park, and Buckingham Fountain.
Our Bikes, Bites & Brews : Signature Tour is designed for those craving the very foods that Chicago is famous for, including samples of Chicago-style pizza and hot dogs and cupcakes and locally-crafted beer all while exploring the Northside’s most popular neighborhoods including Wrigleyville, which is the home of Wrigley Field.
The Bikes, Bites & Brews : Westside Foodie Ride is geared towards foodies, like us, who want to explore the culinary creations and unique ethnic eateries and neighborhoods that make up the diversity that is Chicago. Delight your pallet as we ride through the unique and quirky neighborhoods of Fulton Market, West Town, Wicker Park, Bucktown, Lincoln Park, and back along the Lakefront.
Bobby’s Electric Bikes @ Night Tour is a party on wheels where you can see Chicago’s famous attractions light up at night, including Buckingham Fountain with its world renowned light and sound show. And the Electric bikes make the ride fun and effortless. Wednesdays & Saturdays even include the Lakefront Fireworks from Navy Pier.
The Old Chicago Gangster E-bike Tour, which focuses on the Chicago mafia, takes you into the exciting and seedy past of Chicago’s underworld where you’ll hear fascinating stories about the history of the mob and see their hangouts, some of which still exist today. Oh, and did we mention how much fun the Electric bikes are to ride?
Our kid-friendly tour, Bobby’s Tike Hike: Kid’s Edition, will keep both you and the kids entertained all while showing you the best attractions and activities Chicago has to offer children.
And we even offer specialty tours around the holidays, like Bobby’s Fright Hike: Halloween Edition in the fall and the Icicles on Bicycles during the winter months.