bike tour group in front of a large water fountain with the downtown Chicago skyline in the backgroun

Bike Tours

We’ll Lead the Way
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four people in front of a hot dog mural, enjoying chicago style hot dogs on a food tour

Food Tours

Sample Chicago Classics
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group on a walking tour with a chicago theater sign behind them

Walking Tours

Stroll through Chicago
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Popular Tours of Chicago


  • Chicago Favorites Walking & Food Tour

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    11:30am & 5:30pm Daily

    HIGHLIGHTS: Chicago Food Staples, Deep-Dish Pizza, Chicago-Style Hot Dog, Italian Beef Sandwich, Millennium Park, The Loop, Chicago Riverwalk

    Lou Malnati’s Pizzeria – Wrigley Building
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    Student / Military
    Kids under 12
    Kids under 4
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    Students / Seniors 65+
    Adult
    $69.99 (don't need)
    AGE
    1+
    LENGTH
    1.4 miles
    Custom Line
    11:30am & 5:30pm Daily
    SCHEDULE
    11:30am & 5:30pm Daily
    DURATION
    2.5 to 3 hours
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    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $74.99 $69.99
    Youth (Ages 4-11) $64.99 $59.99
    Infants (Ages 0-3) when sharing w/ adult $10.99 $9.99
    VIP Craft Beer Tasting Upgrade $19.99
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    Bike Tours - We'll Lead the Way

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    Food Tours - Explore by bike or on foot. Schedule a Tour of Chicago for Vacation

    Highlights
    Chicago Loop
    Chicago Style Deep Dish Pizza
    Millennium Park
    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 $69.99
    LEVEL
    Totally Walkable
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  • Bikes, Bites & Brews®- Chicago’s Signature Dishes Bike Tour

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    11:30am & 5:30pm Daily

    HIGHLIGHTS: Deep-dish Pizza, Chicago-Style Hot Dogs, Craft Beer in America's Craft Beer Capital, Brownies or Cupcakes, Day Tour Route: Gold Coast, Wrigley Field, Old Town, Lincoln Park. Night Tour Route: Millennium Park, Navy Pier, Buckingham Fountain

    Bobby’s Bike Hike
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    Kids under 4
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    Students / Seniors 65+
    Student / Military
    Adult
    $84.99
    Custom Line
    11:30am & 5:30pm Daily
    SCHEDULE
    11:30am & 5:30pm Daily
    LENGTH
    13mi / 21km
    AGE
    21+
    DURATION
    4 hours
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    PRICE

    (Discount Online Rate includes Bike, Food & Drinks)

    Price: Fri-Sun Mon-Thurs
    Adults (Ages 21+) $84.99 $79.99
    Electric Bike Upgrade $29.99
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    food tours - explore by bike or on foot

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    walking tours - stroll instead of roll

    PRICE
    Discount Online Rates at $84.99
    LEVEL
    Easy to Moderate
    Highlights
    Gold Coast
    Chicago Style Pizza
    Lincoln Park
    Savory Brownie
    Wrigleyville
    Chicago-style Hot Dog
    Locally Crafted Beer
    Amazing Lakefront
    Gift Certificates
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  • Small Group on Ultimate Chicago Bike Tour

    Chicago’s Ultimate City Bike Tour

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    9:30am Daily (1:30pm Added Weekends)

    HIGHLIGHTS: Chicago Lakefront Trail, Millennium Park & Cloud Gate (a.k.a. The Bean), Grant Park & the Buckingham Fountain, Chicago Theatre, Navy Pier, the Chicago Riverwalk, The Field Museum, Shedd Aquarium, Soldier Field, and Adler Planetarium

    Bobby’s Bike Hike
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    Student / Military
    Kids under 12
    Kids under 4
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    Students / Seniors 65+
    Adult
    $49.99
    AGE
    1+
    DURATION
    3 hours
    LENGTH
    9 mi / 14km
    SCHEDULE
    9:30am Daily
    Custom Line
    9:30am Daily (1:30pm Added Weekends)
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    PRICE

    (Discount Online Rate includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $49.99 $45.99
    Youth (Ages: 4-11) $39.99 $35.99
    Infants (Ages: 0-3) $9.99 $8.99
    Electric Bike Upgrade $29.99
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    Stroll Through Chicago on a Top-Rated Tour

    PRICE
    Discount Online Rates at $49.99
    LEVEL
    Easy
    Highlights
    Museum Campus
    Northerly Island
    Buckingham Fountain
    Adler Planetarium
    Soldier Field
    Grant Park
    Chicago Lakefront
    Amazing Views
    Gift Certificates
    https://fareharbor.com/embeds/book/bobbysbikehike/items/45691/calendar/
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Museums-Parks-at-Sunset.jpg
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  • chinese food on a chinatown food tour

    Chinatown Food & Culture Walking Tour

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    4pm Friday - Sunday, Added 11:30am Saturdays

    HIGHLIGHTS: Cantonese Dim Sum, Portuguese-Chinese Bakery Treats, Xi'an Cuisine, Sichuan Dry Chili Chicken, Yummy Noodles

    Phoenix Restaurant – Chinatown
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    Kids under 12
    Kids under 4
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    Students / Seniors 65+
    Student / Military
    Adult
    $69.99
    LENGTH
    1 mile
    AGE
    1+
    DURATION
    3 hrs
    SCHEDULE
    4pm Fri - Sun, Added 11:30am Saturdays
    Custom Line
    4pm Friday - Sunday, Added 11:30am Saturdays
    Reserve Now
    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $74.99 $69.99
    Youth (Ages 4-11) $64.99 $59.99
    Infants (Ages 0-3) when sharing w/ Adult $10.99 $9.99
    VIP bubbly tea, Beer/Wine Tasting Upgrade $19.99
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    bike tours - we'll lead the way

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    food tours - explore by bike or on foot

    PRICE
    Discount Online Rates at $69.99
    Highlights
    Dry Chili Chicken
    Dim Sum Treats
    Egg Tarts
    Lamb & Cumin Sandwich
    Chinese Cultural Institution
    Award-winning noodles
    VIP Upgrade for beer, wine and bubbly tea
    LEVEL
    Very Easy
    Gift Certificates
    https://fareharbor.com/embeds/book/bobbysbikehike/items/45691/calendar/
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chinatown-Chicago-Culture-and-Food-Tour.jpg
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  • haunted tour chicago

    Bobby’s Fright Hike: Halloween Edition Night Bike Tour

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    October 11 - 31

    HIGHLIGHTS: The Cursed Energy of the John Hancock Center, Lingering Spirits of the SS Eastland, Trapped Souls of the Iroquois Theater, the Ghastly Elegance of the Congress Plaza Hotel

    Bobby’s Bike Hike
    Related Tours
    Student / Military
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Adult
    $49.99
    AGE
    12+
    DURATION
    3 hours
    SCHEDULE
    6pm, October 11 - 31, 2023
    LENGTH
    8mi/13km
    Reserve Now
    PRICE

    (Discount Online Rates includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $49.99 $44.99
    Youth (Ages: 4-11) $29.99 $26.99
    Infants (Ages: 0-3) $9.99 $7.99
    Electric Bike Upgrade $29.99
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    PRICE
    Discount Online Rates at $44.99
    Highlights
    Eastland Disaster
    Rush Street Nightlife
    Chicago River
    Millennium Park
    Cloud Gate
    Buckingham Fountain
    Museum Campus
    Levee District
    Haunted Chicago Stories
    LEVEL
    Mostly Easy
    Custom Line
    October 11 - 31
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/City-Lights-at-Night-walking-tour.jpg
    Gift Certificates
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Discover Chicago Your Way!

Bike & Kayak Rentals in Chicago

  • Flexible rental times
  • Various sizes and styles
  • Kids and adult rental options

couple riding bike rentals near Lake Michigan in Chicago

Bike Rentals

Bike At Your Pace
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Kayak/SUP Rentals

Paddle Lake Michigan
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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.

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Tour with Bobby’s Bike Hike in Miami and Chicago! From visiting popular landmarks to indulging in the local foods, no matter the city you’re exploring, you’ll have an unforgettable experience of the local culture with us.

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