All Tours

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  • Bike Tours
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  • Kayak Tours
  • Food Tours
  • Year-Round Tours
  • Family Friendly
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  • Clear Selection
  • Best way to tour the best pizza joints in chicago

    Bikes, Bites & Brews Tour – Signature Dishes

    12:00pm & 5:30pm Daily

    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 dogs, cupcakes and beer. You'll learn the history behind the foods that made Chicago famous and als...

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    Bobby’s Bike Hike
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Students / Seniors 65+
    $64.75
    Student / Military
    $64.75
    Adult
    $69.75
    SCHEDULE
    12:00pm & 5:30pm Daily
    Custom Line
    12:00pm & 5:30pm Daily
    LENGTH
    13mi / 21km
    DURATION
    4 hours
    PRICE

    (Discount Online Rate includes Bike, Food & Drinks)

    Price: Fri-Sun Mon-Thurs
    Adults $69.75 $66.75
    Students $64.75 $61.75
    Military $64.75 $61.75
    Senior $64.75 $61.75
    Electric Bike Upgrade $19.75
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    PRICE
    Discount Online Rates at $69.75
    LEVEL
    Easy to Moderate
    Highlights
    Gold Coast
    Chicago Style Pizza
    Lincoln Park
    Savory Cupcake
    Wrigleyville
    Chicago-style Hot Dog
    Locally Crafted Beer
    Amazing Lakefront
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/BikesBitesBrewsSignature.jpg
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  • chicago lakefront neighborhood

    Lakefront Neighborhoods Bike Tour

    1:30pm Daily (added 10:30am Weekends)

    Rated the best Chicago sightseeing tour of 2018 by TripAdvisor, Most Organized Bike Ride of Chicago by the Chicago Reader, and Best Chicago Tour by Citysearch make it one of the best, if not the best family-friendly Chicago bike tour! This 'live like a local&#...

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    Bobby’s Bike Hike
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Kids under 4
    $13.75
    Kids under 12
    $25.75
    Adult
    $42.75
    SCHEDULE
    1:30pm Daily (added 10:30am Weekends)
    Custom Line
    1:30pm Daily (added 10:30am Weekends)
    DURATION
    3 hours
    LENGTH
    7 mi/11 km
    PRICE

    (Discount Online Rate includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $47.75 $43.75
    Students $42.75 $38.75
    Military $42.75 $38.75
    Senior $42.75 $38.75
    Kids (under 12) $20.75 $18.75
    Kids (under 4) $10.75 $9.75
    Electric Bike Upgrade $19.75
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    PRICE
    Discount Online Rates at $47.75
    Highlights
    Gold Coast Mansions
    Old Town Historic District
    Lincoln Park Zoo
    North Avenue Beach
    St. Michael’s Church
    Oprah’s Old Chicago home
    Playboy Mansion
    Chicago Lakefront
    LEVEL
    Ridiculously Easy
    Student / Military
    Student
    Students / Seniors 65+
    Students
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Lakefront-Neighborhoods.jpg
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  • Best ways to explore chicago - a food tour!

    Chicago Favorites Walking & Food Tour

    11:30am Daily

    Taste your way through Chicago's most famous recipes on this relaxing and fun Chicago walking food tour. In an exciting two and a half hours, you'll feast on Chicago culinary legends such as deep dish pizza, Italian Beef, a Chicago-style hot dog, and the...

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    Giordano’s Lake Street
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Student / Military
    $43.75
    Adult
    $48.75
    LENGTH
    1.4 miles
    SCHEDULE
    11:30am Daily
    Custom Line
    11:30am Daily
    DURATION
    2.5 to 3 hours
    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $49.75 $46.75
    Students/ $44.75 $41.75
    Military $44.75 $41.75
    Senior $44.75 $41.75
    VIP Craft Beer Tasting Upgrade $19.75
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    Highlights
    Chicago Loop
    Chicago Style Deep Dish Pizza
    Millennium Park
    Famous Chicago-mix popcorn
    Chicago Theater
    Italian Beef Sandwich
    Riverwalk
    Chicago-style Hot Dog
    State Street
    Michigan Avenue
    Dessert
    VIP Craft Beer Package upgrade
    PRICE
    Discount Online Rates at $49.75
    LEVEL
    Totally Walkable
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
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  • Top Craft Brewery Tours Chicago

    Comedy & Craft Beer Walking Tour of Old Town

    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...

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    Second City – Old Town
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Adult
    $60.00
    LENGTH
    1 mile
    DURATION
    2.5 hours
    SCHEDULE
    2:30pm Saturdays
    Custom Line
    2:30pm Saturdays
    PRICE

    (Discount Online Rate includes Beer & Snack Samples)

    Price: Fri-Sun Mon-Thurs
    Adults (21+ Only) $54.75 $54.75
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    Highlights
    Amazing Neighborhoods
    Hidden Pubs
    Well-known Chicago hangouts
    Pilsners
    India Pale Ales
    Belgium Blonds
    PRICE
    Discount Online Rates at $54.75
    LEVEL
    Easy
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2018/03/OldTown.jpg
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  • Chicago Chinatown Food Tours

    Chinatown Food & Culture Walking Tour

    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 on this Chicago Chinatown tour! Chicago's Chinatown, located next door to the Loop on Cermak Street and Wentworth Avenue, b...

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    Pui Tak Center
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Students / Seniors 65+
    $43.75
    Student / Military
    $43.75
    Adult
    $48.75
    LENGTH
    1 mile
    DURATION
    2.5 hrs
    SCHEDULE
    4pm Fri & Sat
    Custom Line
    4pm Friday & Saturday
    PRICE

    (Discount Online Rate includes Food & Beverage Samples)

    Price: Fri-Sun Mon-Thurs
    Adults $49.75 N/A
    Students $44.75 N/A
    Military $44.75 N/A
    Senior $44.75 N/A
    Kids (under 4) $10.75 N/A
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    PRICE
    Discount Online Rates at $49.75
    LEVEL
    Very Easy
    Highlights
    Wentworth Avenue
    Dim Sum Treats
    Egg Tarts
    Lamb & Cumin Sandwich
    Chinese Cultural Institution
    Hot Pots
    Hot Tea
    Beijing Duck
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Chinatown-Chicago-Culture-and-Food-Tour.jpg
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  • bike tours around chicago to park

    Chicago’s ‘Greatest Hits’ Bike Tour

    9am Daily (added 3pm Fridays & Saturdays)

    Experience our "Chicago 101" tour which offers you all of the City's most popular attractions rolled into one memorable activity. This Chicago bike tour includes our most popular parks, fountains, attractions, and lakefront ...

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    Bobby’s Bike Hike
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Kids under 4
    $13.75
    Kids under 12
    $25.75
    Students / Seniors 65+
    $27.75
    Student / Military
    $37.75
    Adult
    $42.75
    DURATION
    2.5 hours
    LENGTH
    6 mi / 10km
    SCHEDULE
    9am Daily (added 3pm Fridays & Saturdays)
    Custom Line
    9am Daily (added 3pm Fridays & Saturdays)
    PRICE

    (Discount Online Rates include bike)

    Price: Fri-Sun Mon-Thurs
    Adults $39.75 $36.75
    Students $34.75 $31.75
    Military $34.75 $31.75
    Senior $34.75 $31.75
    Kids (under 12) $18.75 $15.75
    Kids (under 4) $10.75 $9.75
    Electric Bike Upgrade $19.75
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    PRICE
    Discount Online Rates at $39.75
    LEVEL
    Easy
    Highlights
    Museum Campus
    Northerly Island
    Buckingham Fountain
    Adler Planetarium
    Soldier Field
    Grant Park
    Chicago Lakefront
    Amazing Views
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Museums-Parks-at-Sunset.jpg
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  • Best Pizza Tours in Chicago - Bobby's Bike Hike

    Bikes, Bites & Brews Tour – Westside Foodie Ride

    12:30pm Fri-Sat / 11:30am Sun

    Hop on two wheels and discover a whole new side of Chicago dining! On this Chicago culinary tour, taste your way through diverse neighborhoods as we explore Chicago's immigrant history through food. Enjoy the local eateries and unique...

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    Bobby’s Bike Hike
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Students / Seniors 65+
    $64.75
    Student / Military
    $64.75
    Adult
    $69.75
    SCHEDULE
    12:30pm Fri-Sat / 11:30am Sun
    Custom Line
    12:30pm Fri-Sat / 11:30am Sun
    LENGTH
    12mi / 20km
    DURATION
    4 hours
    PRICE

    (Discount Online Rate includes Bike, Food & Drinks)

    Price: Fri-Sun Mon-Thurs
    Adults $65.75 $63.75
    Students $60.75 $58.75
    Military $60.75 $58.75
    Senior $60.75 $58.75
    Electric Bike Upgrade $19.75
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    PRICE
    Discount Online Rates at $65.75
    LEVEL
    Easy/Moderate
    Highlights
    Fulton Market
    Kuma's Corner (a Chicago burger and banger institution)
    Ukrainian Village
    World Famous Pierogis
    Wicker Park
    Antique Taco, rated '50 best tacos in America'
    Bucktown & 606 Bike Trail
    Locally Crafted Beer
    The ‘Chicago Handshake’
    Lincoln Park
    Scrumptious Macaroons
    Chicago Lakefront Trail
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/BikesBitesBrews-Foodie.jpg
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  • fireworks over chicago

    Chicago Sites @ Night Bike Tour

    7pm Nightly / 7:30pm Fri-Sat

    Our nighttime Chicago bike tour is a Chicago night tour party on wheels! Roll through the Windy City on two-wheels with ease, and see some of our most beautiful landmarks lit up after dark. This tour will ride up and down our incredible lakefront, exploring a few of...

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    Bobby’s Bike Hike
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Adult
    $59.75
    DURATION
    3 hours
    Custom Line
    7pm Nightly / 7:30pm Fri-Sat
    SCHEDULE
    7pm Nightly / 7:30pm Fri-Sat
    LENGTH
    8 mi/13 km
    PRICE

    (Discount Online Rate includes Bike)

    Price: Fri-Sun Mon-Thurs
    Adults $39.75 $36.75
    Students $34.75 $31.75
    Military $34.75 $31.75
    Senior $34.75  $31.75
    Kids (under 4) $10.75  $9.75
    Electric Bike Upgrade $19.75
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    PRICE
    Discount Online Rates at $39.75
    LEVEL
    Mostly Easy to Moderate
    Highlights
    Oak Street Beach
    Rush Street Nightlife
    Chicago River
    Millennium Park
    Cloud Gate at Night
    Buckingham Fountain
    Museum Campus
    Chicago Lakefront & Fireworks
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/City-Lights-at-Night-walking-tour.jpg
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  • Family Friendly Activities in Chicago

    Bobby’s Tike Hike: Kid’s Edition Bike Tour

    2:30pm Daily (May - September)

    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 Kids," our 2-hour, easy riding 4-mile tour is the perfect Chicago tour for you and your energetic...

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    Bobby’s Bike Hike
    Student / Military
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Kids under 12
    $19.50
    Students / Seniors 65+
    $27.75
    Adult
    $34.75
    Kids under 4
    $9.75
    DURATION
    2 hours
    Custom Line
    2:30pm Daily (May - September)
    SCHEDULE
    2:30pm Daily (May - September)
    LENGTH
    4.5 miles
    PRICE

    (Discount Online Rates include Bike)

    Price: Fri-Sun Mon-Thurs
    Adults $39.75 $36.75
    Students $34.75 $31.75
    Military $34.75 $31.75
    Senior $34.75 $31.75
    Kids (under 12) $15.75 $14.75
    Kids (under 4) FREE FREE
    Electric Bike Upgrade $19.75
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    PRICE
    Discount Online Rates at $39.75. Kid's under 4 FREE
    LEVEL
    Easy, Easy, Easy
    Highlights
    Lincoln Park Zoo
    Chicago Lakefront
    Oak Street Beach
    Children’s Fountain
    Petting Zoo
    Peggy Notebaert Nature Museum
    Abe Lincoln Stature
    Kissing Bridge
    Secret Garden
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Tike-Hike-KidsEdition.jpg
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  • Chicago Mafia Mob Tours

    Old Chicago Gangster Electric Bike Tour

    Private Groups Only

    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 crazy and colorful people and places of Chicago's bygone gangster days. Our Old Chicago Gangster e...

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    Bobby’s Bike Hike
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    LEVEL
    Moderate/Intermediate
    Students / Seniors 65+
    $47.75
    Student / Military
    $47.75
    Adult
    $52.75
    LENGTH
    16mi/26km
    DURATION
    4 hours
    PRICE

    (includes Electric Bike)

    Price: Fri-Sun Mon-Thurs
    Adults $55.75 $55.75
    Students (16+) $50.75 $50.75
    Military $50.75 $50.75
    Senior $50.75 $50.75
    Electric Bike Upgrade $19.75
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    Highlights
    Bridgeport
    Chinatown
    Old Palmisano Park
    Old Italian Outfit hangouts
    McCormick Place
    Prairie Ave District
    Levee Red Light District
    Italian Beef Sandwich
    Chicago Lakefront
    SCHEDULE
    Private Groups Only
    Custom Line
    Private Groups Only
    PRICE
    Starting at $50.75
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Southside-Gangster.jpg
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  • Cocktails and desserts tours in Chicago

    Sweets & Spirits Dessert Walking Tour

    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 &...

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    Chicago Cultural Center
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Students / Seniors 65+
    $45.75
    Student / Military
    $45.75
    Adult
    $50.75
    LENGTH
    1 mile
    DURATION
    2.5 hours
    PRICE

    (includes Food & Beverage Samples)

    Price: Fri-Sun Mon-Thurs
    Adults $59.75 $59.75
    Students $54.75 $54.75
    Military $54.75 $54.75
    Senior $54.75 $54.75
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    LEVEL
    Easy
    Highlights
    Michigan Avenue
    Decadent Treats
    River North Nightlife
    Trendy Cocktails
    Local Chocolates
    Dylan’s Candy Store
    Fun, Fun, Fun
    SCHEDULE
    Private Groups Only
    Custom Line
    Private Groups Only
    PRICE
    Starting at: $54.75
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
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  • Book a walking tour of Chicago River

    Chicago River Walking Tour

    Private Groups Only

    Our private walking tour is the perfect way to learn all about the history and breathtaking infrastructure of the Chicago River! On this Chicago tour, we will explore the rolling promenades, historic landmarks, and relaxing mini-parks that frame the legendary waterway. O...

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    Reserve Private Tour
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Students / Seniors 65+
    $20.00
    Student / Military
    $20.00
    Adult
    $25.00
    LENGTH
    1 mile
    DURATION
    1.5 hours
    PRICE
    Price: Fri-Sun Mon-Thurs
    Adults $39.75 $39.75
    Students $34.75 $34.75
    Military $34.75 $34.75
    Senior $34.75 $34.75
    Kids (under 12) $20.75 $20.75
    Kids (under 4) $10.75 $10.75
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    Highlights
    Chicago Riverwalk
    Amazing Architecture
    Wrigley Building
    Vietnam Memorial & Park
    McCormick Bridge house and River Museum
    Centennial Fountain & Water Arc
    Gorgeous Bridges
    Chicago’s Lakefront
    LEVEL
    Easy
    SCHEDULE
    Private Groups Only
    Custom Line
    Private Groups Only
    PRICE
    Starting at $20.75
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Chicago-River-walking-tour.jpg
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  • Things to do for Halloween in Chicago

    Bobby’s Fright Hike: Halloween Edition Night Bike Tour

    RESUMES OCTOBER 2019

    Only in Chicago can you be scared witless while enjoying a rip-roaring entertaining bicycle tour! Bobby's Fright Hike - Halloween Edition bike tour is a three-hour guided adventure through Chicago's spookiest spots. On this Chi...

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    Bobby’s Bike Hike
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Students / Seniors 65+
    $40.75
    Student / Military
    $40.75
    Adult
    $45.75
    DURATION
    3 hours
    LENGTH
    8mi/13km
    PRICE

    (Discount Online Rates includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $45.75 $39.75
    Students $40.75 $34.75
    Military $40.75 $34.75
    Senior $40.75 $34.75
    Electric Bike Upgrade $19.75
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    PRICE
    Discount Online Rates at $45.75
    Highlights
    Eastland Disaster
    Rush Street Nightlife
    Chicago River
    Millennium Park
    Cloud Gate
    Buckingham Fountain
    Museum Campus
    Levee District
    Haunted Chicago Stories
    LEVEL
    Mostly Easy
    SCHEDULE
    RESUMES OCTOBER 2019
    Custom Line
    RESUMES OCTOBER 2019
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/City-Lights-at-Night-walking-tour.jpg
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  • Holiday tour in Chicago with Food

    Holiday Hike: Season Sampling Walking & Food Tour

    RESUMES NOVEMBER 2019

    Holiday Hike: Season Sampling Walking Tour Taste your way through the holiday season on this food and beverage walking tour! This holiday-themed tour begins at the end of November and runs through Christmas Eve. Bobby's Holiday Hike is a great way to experience all that Chicago has to offer duri...

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    Giordano’s Lake Street
    Kids under 12
    Kids under 4
    Gift Certificates
    Array
    Private Group Request
    Array
    Reserve Now
    Array
    Students / Seniors 65+
    $50.75
    Student / Military
    $50.75
    Adult
    $55.75
    LENGTH
    1.25 mile
    DURATION
    2.5 hours
    Highlights

    Park's Christmas Tree
    Ice Skating Rink
    State Street's Holiday Lights
    Marshall Field's Walnut Room
    Brownie samples
    Seasonal craft beer
    Chicago-style pizza
    German cider
    PRICE

    (Discount Online Rate includes Food & Beverage Samples)

    Price: Fri-Sun Mon-Thurs
    Adults $54.75 $54.75
    Students $49.75 $49.75
    Military $49.75 $49.75
    Senior $49.75 $49.75
    Kids (under 4) $9.75 $9.75

     

     

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    PRICE
    Discount Online Rates at $54.75
    LEVEL
    Festively Easy
    SCHEDULE
    RESUMES NOVEMBER 2019
    Custom Line
    RESUMES NOVEMBER 2019
    Map Graphic
    https://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
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Take Off on Unique Tours of Chicago With Bobby’s Bike Hike

When you visit a new place, you want to see what it has to offer. What better way than to experience it all firsthand with a Chicago tour. From interacting with people on the streets to hitting the town’s hottest restaurants or exploring sights a little off the beaten path, you can learn more about a city by taking a tour than you would reading about it or getting the scoop online.

Get out and experience Chicago with a city tour from Bobby’s Bike Hike. Our engaging guides can take you around while you enjoy the fresh air on our biking or walking tours. Indulge in delicious bites to eat along the way when you sign up for one of our foodie expeditions. Whatever option you choose, you will get to know Chicago and see it from a fresh new perspective.