Private Tours of Chicago

All Classic Bike, Food and Walking Tours are Available for Private Bookings

Our sole purpose is to educate, entertain and help in any way we can!

For groups looking for a private tour of Chicago please feel free to call 312.245.9300 with questions, ideas, or comments. You may also contact us using the private tours form below.

With a private tour, you can lean on us to help with the planning, from the number of people on the tour to the best places to visit for your group, Bobby’s Bike Hike has the experience and expertise in creating private tour itineraries to fit every occasion and every group size.

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All Tours Are Available For Private Bookings

  • Chicago Deep-Dish Pizza

    Bikes, Bites & Brews®- Chicago’s Signature Dishes Bike Tour

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    11:30am & 5:30pm Daily (12pm Sundays)

    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
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Related Tours
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    Private Group Request
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    Adult
    $76.99
    SCHEDULE
    11:30am & 5:30pm Daily (12pm Sundays)
    Custom Line
    11:30am & 5:30pm Daily (12pm Sundays)
    LENGTH
    13mi / 21km
    AGE
    21+
    DURATION
    4 hours
    Reserve Now
    PRICE

    (Discount Online Rate includes Bike, Food & Drinks)

    Price: Fri-Sun Mon-Thurs
    Adults (Ages 21+) $79.99 $76.99
    Squad Price: Private Group (up to 9 people) $649.99 $649.99
    Electric Bike Upgrade $19.99
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    PRICE
    Discount Online Rates at $76.99
    LEVEL
    Easy to Moderate
    Highlights
    Gold Coast
    Chicago Style Pizza
    Lincoln Park
    Savory Brownie
    Wrigleyville
    Chicago-style Hot Dog
    Locally Crafted Beer
    Amazing Lakefront
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrewsSignature.jpg
    Gift Certificates
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  • Active Chicago Food Tours

    Chicago Favorites Walking & Food Tour

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    11:30am 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
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Related Tours
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    Private Group Request
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    Adult
    $54.99 (don't need)
    AGE
    1+
    LENGTH
    1.4 miles
    SCHEDULE
    11:30am Daily
    Custom Line
    11:30am Daily
    DURATION
    2.5 to 3 hours
    Reserve Now
    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $59.99 $54.99
    Youth (Ages 4-11) $54.99 $49.99
    Infants (Ages 0-3) when sharing w/ adult $10.99 $9.99
    Squad Price: Private Group(up to 9 people) $549.99 $549.99
    VIP Craft Beer Tasting Upgrade $19.99
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    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 $54.99
    LEVEL
    Totally Walkable
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
    Gift Certificates
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  • Lakefront Neighborhoods Bike Tour

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    1:30pm Weekdays, 10:30am & 2:30pm Weekends

    HIGHLIGHTS: Family Friendly, Streeterville, Museum of Contemporary Art, Gold Coast, Playboy Mansion, Lincoln Park & Lincoln Park Zoo, Old Town, St. Michael's Church, North Avenue Beach, the Chicago Lakefront Trail

    Bobby’s Bike Hike
    Student / Military
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Related Tours
    Array
    Private Group Request
    Array
    Adult
    $39.99
    AGE
    1+
    SCHEDULE
    1:30pm Weekdays, 10:30am & 2:30pm Weekends
    Custom Line
    1:30pm Weekdays, 10:30am & 2:30pm Weekends
    DURATION
    3 hours
    LENGTH
    7 mi/11 km
    Reserve Now
    PRICE

    (Discount Online Rate includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $42.99 $39.99
    Youth (Ages: 4-11) $25.99 $22.99
    Infants (Ages: 0-3) $5.99 $4.99
    Squad Price (Private Groups up to 9 people) $349.99 $349.99
    Electric Bike Upgrade $19.99
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    PRICE
    Discount Online Rates at $39.99
    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
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Lakefront-Neighborhoods.jpg
    Gift Certificates
    {"text":"Gift Certificates","link":"https:\/\/fareharbor.com\/embeds\/book\/bobbysbikehike\/items\/45691\/calendar\/?u=9efbf3d0-ddae-4331-8765-6f33490d72a6&from-ssl=yes&ga=UA-46449336-1,388302409.1507320438%3BUA-16142268-1,388302409.1507320438%3B","page_id":"3490","use_internal":"false"}
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  • Small Group on Ultimate Chicago Bike Tour

    Chicago’s Ultimate City Bike Tour

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    9:30am Daily

    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
    Student / Military
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Related Tours
    Array
    Gift Certificates
    Array
    Private Group Request
    Array
    Adult
    $39.99
    AGE
    1+
    DURATION
    3 hours
    LENGTH
    9 mi / 14km
    SCHEDULE
    9:30am Daily
    Custom Line
    9:30am Daily
    Reserve Now
    PRICE

    (Discount Online Rate includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $45.99 $40.99
    Youth (Ages: 4-11) $39.99 $35.99
    Infants (Ages: 0-3) $9.99 $8.99
    Squad Price: Private Group (up to 9 people) $349.99 $349.99
    Electric Bike Upgrade $19.99
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    PRICE
    Discount Online Rates at $39.99
    LEVEL
    Easy
    Highlights
    Museum Campus
    Northerly Island
    Buckingham Fountain
    Adler Planetarium
    Soldier Field
    Grant Park
    Chicago Lakefront
    Amazing Views
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Museums-Parks-at-Sunset.jpg
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  • Chicago-style Pizza on Food Tour with Bobby's Bike Hike

    Westside Foodie Ride Bike Tour

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    12pm Fri-Sat / 11:30am Sun

    HIGHLIGHTS: Best Burgers on the Planet, Craft Beer (VIP Upgrade), Polish Pierogi, Gourmet Tacos, Rich Drinking Chocolate, Fulton Market, Ukrainian Village, Wicker Park, Old Town, Lake Michigan

    Bobby’s Bike Hike
    Student / Military
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Related Tours
    Array
    Gift Certificates
    Array
    Private Group Request
    Array
    Adult
    $69.99
    SCHEDULE
    12:30pm Fri-Sat / 11:30am Sun
    LENGTH
    12mi / 20km
    Custom Line
    12pm Fri-Sat / 11:30am Sun
    AGE
    21+
    DURATION
    4 hours
    Reserve Now
    PRICE

    (Discount Online Rate includes Bike and Food, VIP Drink optional)

    Price: Fri-Sun Mon-Thurs
    Adults (Ages 21+) $74.99 $69.99
    Squad Price (Private Groups up to 9 people) $649.99 $649.99
    VIP Alcohol Pairing Upgrade $19.99
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    PRICE
    Discount Online Rates at $74.99
    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 (VIP Upgrade)
    Lincoln Park
    Artisan chocolate
    Chicago Lakefront Trail
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrews-Foodie.jpg
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  • chicago halloween tour

    Bobby’s Fright Hike: Halloween Edition Night Bike Tour

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    Starting October 13

    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+
    Private Group Request
    Array
    Adult
    $39.99
    AGE
    12+
    DURATION
    3 hours
    LENGTH
    8mi/13km
    Reserve Now
    PRICE

    (Discount Online Rates includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $42.99 $39.99
    Youth (Ages: 4-11) $29.99 $26.99
    Infants (Ages: 0-3) $9.99 $7.99
    Squad Price (Private Groups up to 9 people) $349.99 $349.99
    Electric Bike Upgrade $19.99
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    PRICE
    Discount Online Rates at $39.99
    Highlights
    Eastland Disaster
    Rush Street Nightlife
    Chicago River
    Millennium Park
    Cloud Gate
    Buckingham Fountain
    Museum Campus
    Levee District
    Haunted Chicago Stories
    LEVEL
    Mostly Easy
    SCHEDULE
    Starting October 13
    Custom Line
    Starting October 13
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/City-Lights-at-Night-walking-tour.jpg
    Gift Certificates
    {"text":"","link":"","page_id":"3490","use_internal":""}
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  • Chinatown Food & Culture Walking Tour

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    4pm Friday & Saturday

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

    Phoenix Restaurant – Chinatown
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Related Tours
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    Gift Certificates
    Array
    Private Group Request
    Array
    Adult
    $54.99
    LENGTH
    1 mile
    AGE
    1+
    DURATION
    2.5 hrs
    SCHEDULE
    4pm Fri & Sat
    Custom Line
    4pm Friday & Saturday
    Reserve Now
    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $59.99 $54.99
    Youth (Ages 4-11) $54.99 $49.99
    Infants (Ages 0-3) when sharing w/ Adult $9.99 $8.99
    Squad Price (Private Groups up to 9 people) $549.99 $549.99
    VIP bubbly tea, Beer/Wine Tasting Upgrade $19.99
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    PRICE
    Discount Online Rates at $54.99
    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
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chinatown-Chicago-Culture-and-Food-Tour.jpg
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  • chicago holiday market walking tour

    Chicago-style Holiday Hike: Season Sampling Walking & Food Tour

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    RESUMES NOVEMBER 2021

    HIGHLIGHTS: Traditional German Christmas Market, Millennium Park Christmas Tree, Deep-Dish Pizza, Chicago-Style Hot Dog, Marshall Fields Holiday Window Displays, Hot Cocoa

    Lou Malnati’s Pizzeria – Wrigley Building
    Related Tours
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Private Group Request
    Array
    Adult
    $69.99
    AGE
    1+
    LENGTH
    1.25 mile
    DURATION
    2.5 to 3 hours
    Gift Certificates
    Reserve Now
    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $69.99 $64.99
    Youth (Ages: 4-11) $64.99 $59.99
    Infants (Ages: 0-3) when sharing w/ Adult $10.99 $9.99
    Squad Price (Private groups up to 9 people) $549.99 $549.99
    VIP Holiday Cocktail/Beer Tasting Upgrade $19.99
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    Highlights
    Christkindlmarket
    Millennium Park's Christmas Tree
    Deluxe Hot Cocoa
    Ice Skating Rink
    State Street's Holiday Lights
    Marshall Field's Walnut Room
    The original Brownie recipe
    Chicago-style pizza
    German holiday food
    Locally-crafted Holiday spirits (for an additional fee)
    PRICE
    Discount Online Rates at $69.99
    LEVEL
    Festively Easy
    SCHEDULE
    RESUMES NOVEMBER 2021
    Custom Line
    RESUMES NOVEMBER 2021
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
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