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

  • Active Chicago Food Tours

    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
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Related Tours
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    Adult
    $69.99 (don't need)
    AGE
    1+
    LENGTH
    1.4 miles
    SCHEDULE
    11:30am & 5:30pm Daily
    Custom Line
    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 $69.99 $65.99
    Youth (Ages 4-11) $59.99 $55.99
    Infants (Ages 0-3) when sharing w/ adult $10.99 $9.99
    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 $69.99
    LEVEL
    Totally Walkable
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
    Gift Certificates
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  • chicago holiday market walking tour

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

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    November 19 - December 24, 2022

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

    Lou Malnati’s Pizzeria – Wrigley Building
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    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Private Group Request
    Array
    Adult
    $69.99
    AGE
    1+
    LENGTH
    1.25 mile
    SCHEDULE
    11:30am Daily
    DURATION
    2.5 to 3 hours
    Gift Certificates
    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 Holiday Cocktail/Beer Tasting Upgrade $19.99
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    Highlights
    Christkindlmarket
    Millennium Park's Christmas Tree
    Deluxe Hot Apple Cider
    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
    Custom Line
    November 19 - December 24, 2022
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
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  • bobby's bike hike holiday stroll through Chicago

    Chicago’s Seasonal Stroll – Walking Tour

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    November 19 - December 24, 2022

    HIGHLIGHTS: Traditional German Christmas Market, Millennium Park Christmas Tree, Magnificent Mile Shopping district, Wrigley Building Christmas display, Marshall Fields Holiday Window Displays, Chicago Theatre

    Petterino’s Restaurant
    Related Tours
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Private Group Request
    Array
    Adult
    $29.99
    AGE
    1+
    LENGTH
    1.25 mile
    DURATION
    2 hours
    SCHEDULE
    3:30pm Daily
    Gift Certificates
    Reserve Now
    PRICE

    (Discounted Online Rates Shown)

    Price: Fri-Sun Mon-Thurs
    Adults $29.99 $29.99
    Youth (Ages: 4-11) $25.99 $25.99
    Infants (Ages: 0-3) $9.99 $9.99
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    LEVEL
    An easy stroll
    Highlights
    Christkindlmarket
    Millennium Park's Christmas Tree
    Ice Skating Rink
    State Street and Michigan Avenue Holiday Lights
    Marshall Field's (Macy's)
    Wrigley Building
    Chicago Theatre
    PRICE
    Discount Online Rates at $29.99
    Custom Line
    November 19 - December 24, 2022
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
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  • 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
    $84.99
    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+) $84.99 $79.99
    Electric Bike Upgrade $29.99
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    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
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrewsSignature.jpg
    Gift Certificates
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  • 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
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Related Tours
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    Private Group Request
    Array
    Adult
    $69.99
    LENGTH
    1 mile
    AGE
    1+
    DURATION
    2.5 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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    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
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chinatown-Chicago-Culture-and-Food-Tour.jpg
    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
    Student / Military
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Related Tours
    Array
    Private Group Request
    Array
    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)
    Reserve Now
    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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    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
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Museums-Parks-at-Sunset.jpg
    Gift Certificates
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  • Lakefront Neighborhoods Bike Tour

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    1:30pm Weekdays, 10:30am 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
    $49.99
    AGE
    1+
    SCHEDULE
    1:30pm Weekdays, 10:30am Weekends
    Custom Line
    1:30pm Weekdays, 10:30am Weekends
    DURATION
    3 hours
    LENGTH
    7 mi/11 km
    Reserve Now
    PRICE

    (Discount Online Rate includes bike)

    Price: Fri-Sun Mon-Thurs
    Adults $49.99 $45.99
    Youth (Ages: 4-11) $29.99 $25.99
    Infants (Ages: 0-3) $7.99 $6.99
    Electric Bike Upgrade $29.99
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    PRICE
    Discount Online Rates at $49.99
    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
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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
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Related Tours
    Array
    Private Group Request
    Array
    Adult
    $84.99
    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+) $84.99 $79.99
    VIP Alcohol Pairing Upgrade $19.99
    Electric Bike Upgrade $29.99
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    PRICE
    Discount Online Rates at $84.99
    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
    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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