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.

  • This field is for validation purposes and should be left unchanged.

All Tours Are Available For Private Bookings

  • Active Chicago Food Tours

    Chicago Favorites Walking & Food Tour

    Learn More
    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
    Array
    Private Group Request
    Array
    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
    Bottom Link -1

    Bottom Link -2

    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
    {"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"}
    Learn More
  • chicago holiday market walking tour

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

    Learn More
    11:30am Daily

    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
    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
    SCHEDULE
    11:30am Daily
    Custom Line
    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 $69.99 $64.99
    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
    Bottom Link -2

    Bottom Link -1

    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
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
    Learn More
  • bobby's bike hike holiday stroll through chicago

    Chicago’s Seasonal Stroll – Walking Tour

    Learn More
    3:30pm Daily

    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
    Custom Line
    3:30pm Daily
    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
    Bottom Link -2

    Bottom Link -1

    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
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
    Learn More

  • Chinatown Food & Culture Walking Tour

    Learn More
    4pm Friday through Sunday

    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
    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 through Sunday
    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
    Bottom Link -2

    Bottom Link -1

    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
    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"}
    Learn More
  • Chicago Deep-Dish Pizza

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

    Learn More
    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
    Array
    Private Group Request
    Array
    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
    Bottom Link -2

    Bottom Link -1

    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
    {"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"}
    Learn More
  • Small Group on Ultimate Chicago Bike Tour

    Chicago’s Ultimate City Bike Tour

    Learn More
    9:30am & 1:30pm 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
    Private Group Request
    Array
    Adult
    $39.99
    AGE
    1+
    DURATION
    3 hours
    LENGTH
    9 mi / 14km
    Custom Line
    9:30am & 1:30pm Daily
    SCHEDULE
    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
    Bottom Link -1

    Bottom Link -2

    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
    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"}
    Learn More
  • kids riding bikes with Bobby's Bike Hike on Chicago family friendly tour

    Chicago Family Food & Bike Tour (with Top Attractions)

    Learn More
    11:00am & 4:30pm Daily

    HIGHLIGHTS: Chicago Food Staples, Deep-Dish Pizza, Chicago-Style Hot Dog, Dessert, Millennium Park, The Loop, Navy Pier

    Bobby’s Bike Hike
    Kids under 12
    Kids under 4
    Students / Seniors 65+
    Student / Military
    Related Tours
    Array
    Private Group Request
    Array
    Adult
    $61.99
    AGE
    1+
    SCHEDULE
    11:00am & 4:30pm Daily
    Custom Line
    11:00am & 4:30pm Daily
    DURATION
    4 hours
    LENGTH
    9mi / 14km
    Reserve Now
    PRICE

    (Discount Online Rate includes Bike, Food & Water)

    Price: Fri-Sun Mon-Thurs
    Adults(Ages: 12+) $69.99 $65.99
    Youth (Ages 4-11) $59.99 $55.99
    Infant(under 4 – if no extra food required) $10.99 $9.99
    Squad Price (Private Groups up to 9 people) $649.99 $649.99
    Electric Bike Upgrade $19.99
    VIP Craft Beer Upgrade $19.99
    Bottom Link -2

    Bottom Link -1

    Highlights
    Deep-dish Pizza
    Gold Coast
    Millennium Park
    Chicago Riverwalk
    Chicago-style Hot Dog
    Buckingham Fountain
    Gelato
    Craft Beer
    Lakefront Trail
    Oak Street Beach
    PRICE
    Discount Online Rates at $65.99
    LEVEL
    Easy
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/City-Lights-at-Night-walking-tour.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"}
    Learn More
  • Chicago-style Pizza on Food Tour with Bobby's Bike Hike

    Westside Foodie Ride Bike Tour

    Learn More
    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
    $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
    Bottom Link -2

    Bottom Link -1

    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
    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"}
    Learn More