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.
All Tours Are Available For Private Bookings
Chicago Favorites Walking & Food Tour
Learn More11:30am & 5:30pm DailyHIGHLIGHTS: Chicago Food Staples, Deep-Dish Pizza, Chicago-Style Hot Dog, Italian Beef Sandwich, Millennium Park, The Loop, Chicago Riverwalk
Lou Malnati’s Pizzeria – Wrigley BuildingKids under 12Kids under 4Students / Seniors 65+Student / MilitaryRelated ToursArrayPrivate Group RequestArrayAdult$69.99 (don't need)AGE1+LENGTH1.4 milesSCHEDULE11:30am & 5:30pm DailyCustom Line11:30am & 5:30pm DailyDURATION2.5 to 3 hoursReserve NowPRICE(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 Bottom Link -1
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HighlightsChicago 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 upgradePRICEDiscount Online Rates at $69.99LEVELTotally WalkableMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpgGift 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"}
Chicago-style Holiday Hike: Season Sampling Food & Walking Tour
Learn MoreNovember 19 - December 24, 2022HIGHLIGHTS: 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 BuildingRelated ToursKids under 12Kids under 4Students / Seniors 65+Student / MilitaryPrivate Group RequestArrayAdult$69.99AGE1+LENGTH1.25 mileSCHEDULE11:30am DailyDURATION2.5 to 3 hoursGift CertificatesReserve NowPRICE(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 Bottom Link -2Bottom Link -1HighlightsChristkindlmarket
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)PRICEDiscount Online Rates at $69.99LEVELFestively EasyCustom LineNovember 19 - December 24, 2022Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
Chicago’s Seasonal Stroll – Walking Tour
Learn MoreNovember 19 - December 24, 2022HIGHLIGHTS: 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 RestaurantRelated ToursKids under 12Kids under 4Students / Seniors 65+Student / MilitaryPrivate Group RequestArrayAdult$29.99AGE1+LENGTH1.25 mileDURATION2 hoursSCHEDULE3:30pm DailyGift CertificatesReserve NowPRICE(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 -2Bottom Link -1LEVELAn easy strollHighlightsChristkindlmarket
Millennium Park's Christmas Tree
Ice Skating Rink
State Street and Michigan Avenue Holiday Lights
Marshall Field's (Macy's)
Wrigley Building
Chicago TheatrePRICEDiscount Online Rates at $29.99Custom LineNovember 19 - December 24, 2022Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
Bikes, Bites & Brews®- Chicago’s Signature Dishes Bike Tour
Learn More11:30am & 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 HikeKids under 12Kids under 4Students / Seniors 65+Student / MilitaryRelated ToursArrayPrivate Group RequestArrayAdult$84.99SCHEDULE11:30am & 5:30pm Daily (12pm Sundays)Custom Line11:30am & 5:30pm Daily (12pm Sundays)LENGTH13mi / 21kmAGE21+DURATION4 hoursReserve NowPRICE(Discount Online Rate includes Bike, Food & Drinks)
Price: Fri-Sun Mon-Thurs Adults (Ages 21+) $84.99 $79.99 Electric Bike Upgrade $29.99 Bottom Link -2Bottom Link -1
PRICEDiscount Online Rates at $84.99LEVELEasy to ModerateHighlightsGold Coast
Chicago Style Pizza
Lincoln Park
Savory Brownie
Wrigleyville
Chicago-style Hot Dog
Locally Crafted Beer
Amazing LakefrontMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrewsSignature.jpgGift 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"}
Chinatown Food & Culture Walking Tour
Learn More4pm Friday - Sunday, Added 11:30am SaturdaysHIGHLIGHTS: Cantonese Dim Sum, Portuguese-Chinese Bakery Treats, Xi'an Cuisine, Sichuan Dry Chili Chicken, Yummy Noodles
Phoenix Restaurant – ChinatownKids under 12Kids under 4Students / Seniors 65+Student / MilitaryRelated ToursArrayPrivate Group RequestArrayAdult$69.99LENGTH1 mileAGE1+DURATION2.5 hrsSCHEDULE4pm Fri - Sun, Added 11:30am SaturdaysCustom Line4pm Friday - Sunday, Added 11:30am SaturdaysReserve NowPRICE(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 Bottom Link -2Bottom Link -1PRICEDiscount Online Rates at $69.99HighlightsDry Chili Chicken
Dim Sum Treats
Egg Tarts
Lamb & Cumin Sandwich
Chinese Cultural Institution
Award-winning noodles
VIP Upgrade for beer, wine and bubbly teaLEVELVery EasyMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chinatown-Chicago-Culture-and-Food-Tour.jpgGift 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"}
Chicago’s Ultimate City Bike Tour
Learn More9:30am 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 HikeStudent / MilitaryKids under 12Kids under 4Students / Seniors 65+Related ToursArrayPrivate Group RequestArrayAdult$49.99AGE1+DURATION3 hoursLENGTH9 mi / 14kmSCHEDULE9:30am DailyCustom Line9:30am Daily (1:30pm Added Weekends)Reserve NowPRICE(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 Bottom Link -1Bottom Link -2PRICEDiscount Online Rates at $49.99LEVELEasyHighlightsMuseum Campus
Northerly Island
Buckingham Fountain
Adler Planetarium
Soldier Field
Grant Park
Chicago Lakefront
Amazing ViewsMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Museums-Parks-at-Sunset.jpgGift 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"}
Lakefront Neighborhoods Bike Tour
Learn More1:30pm Weekdays, 10:30am WeekendsHIGHLIGHTS: 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 HikeStudent / MilitaryKids under 12Kids under 4Students / Seniors 65+Related ToursArrayPrivate Group RequestArrayAdult$49.99AGE1+SCHEDULE1:30pm Weekdays, 10:30am WeekendsCustom Line1:30pm Weekdays, 10:30am WeekendsDURATION3 hoursLENGTH7 mi/11 kmReserve NowPRICE(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 Bottom Link -1Bottom Link -2PRICEDiscount Online Rates at $49.99HighlightsGold Coast Mansions
Old Town Historic District
Lincoln Park Zoo
North Avenue Beach
St. Michael’s Church
Oprah’s Old Chicago home
Playboy Mansion
Chicago LakefrontLEVELRidiculously EasyMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Lakefront-Neighborhoods.jpgGift 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"}
Westside Foodie Ride Bike Tour
Learn More12pm Fri-Sat / 11:30am SunHIGHLIGHTS: 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 HikeKids under 12Kids under 4Students / Seniors 65+Student / MilitaryRelated ToursArrayPrivate Group RequestArrayAdult$84.99SCHEDULE12:30pm Fri-Sat / 11:30am SunLENGTH12mi / 20kmCustom Line12pm Fri-Sat / 11:30am SunAGE21+DURATION4 hoursReserve NowPRICE(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 Bottom Link -2Bottom Link -1PRICEDiscount Online Rates at $84.99LEVELEasy/ModerateHighlightsFulton 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 TrailMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrews-Foodie.jpgGift 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"}