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 BuildingButton URL Seconday HeaderStudent / MilitaryKids under 12Kids under 4Number Secondary HeaderLogo Secondary HeaderGift CertificatesStudents / Seniors 65+Adult$69.99 (don't need)AGE1+LENGTH1.4 milesCustom Line11:30am & 5:30pm DailySCHEDULE11:30am & 5:30pm DailyDURATION2.5 to 3 hoursReserve 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 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 WalkableLogo URL Secondary Headerhttps://www.bobbysbikehike.com/Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpgRelated ToursArrayPrivate Group RequestArray
Bikes, Bites & Brews®- Chicago’s Signature Dishes Bike Tour
Learn More11:30am & 5:30pm DailyHIGHLIGHTS: 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 HikeButton URL Seconday HeaderKids under 12Kids under 4Number Secondary HeaderLogo Secondary HeaderStudents / Seniors 65+Student / MilitaryAdult$84.99Custom Line11:30am & 5:30pm DailySCHEDULE11:30am & 5:30pm DailyLENGTH13mi / 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 LakefrontGift Certificateshttps://fareharbor.com/embeds/book/bobbysbikehike/items/45691/calendar/Logo URL Secondary Headerhttps://www.bobbysbikehike.com/Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/BikesBitesBrewsSignature.jpgRelated ToursArrayPrivate Group RequestArray
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 HikeButton URL Seconday HeaderStudent / MilitaryKids under 12Kids under 4Number Secondary HeaderLogo Secondary HeaderStudents / Seniors 65+Adult$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 ViewsGift Certificateshttps://fareharbor.com/embeds/book/bobbysbikehike/items/45691/calendar/Logo URL Secondary Headerhttps://www.bobbysbikehike.com/Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Museums-Parks-at-Sunset.jpgRelated ToursArrayPrivate Group RequestArray
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 – ChinatownButton URL Seconday HeaderKids under 12Kids under 4Number Secondary HeaderLogo Secondary HeaderStudents / Seniors 65+Student / MilitaryAdult$69.99LENGTH1 mileAGE1+DURATION3 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 EasyGift Certificateshttps://fareharbor.com/embeds/book/bobbysbikehike/items/45691/calendar/Logo URL Secondary Headerhttps://www.bobbysbikehike.com/Map Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chinatown-Chicago-Culture-and-Food-Tour.jpgRelated ToursArrayPrivate Group RequestArray
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 HikeKids under 12Kids under 4Students / Seniors 65+Student / MilitaryAdult$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"}Related ToursArrayPrivate Group RequestArray
Westside Foodie Ride Bike Tour
Learn More12pm Fri-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 HikeButton URL Seconday HeaderKids under 12Kids under 4Number Secondary HeaderLogo Secondary HeaderStudents / Seniors 65+Student / MilitaryAdult$84.99SCHEDULE12:30pm Fri-SunLENGTH12mi / 20kmCustom Line12pm Fri-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 TrailLogo URL Secondary Headerhttps://www.bobbysbikehike.com/Map 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"}Related ToursArrayPrivate Group RequestArray
Chicago Family Food & Bike Tour (with Top Attractions)
Learn More11:00am DailyHIGHLIGHTS: Chicago Food Staples, Deep-Dish Pizza, Chicago-Style Hot Dog, Dessert, Millennium Park, The Loop, Navy Pier
Bobby’s Bike HikeKids under 12Kids under 4Students / Seniors 65+Student / MilitaryAdult$74.99AGE1+Custom Line11:00am DailySCHEDULE11:00am DailyDURATION4 hoursLENGTH9mi / 14kmReserve NowPRICE(Discount Online Rate includes Bike, Food & Water)
Price: Fri-Sun Mon-Thurs Adults(Ages: 12+) $74.99 $69.99 Youth (Ages 4-11) $64.99 $59.99 Infant(under 4 – if no extra food required) $10.99 $9.99 Electric Bike Upgrade $29.99 VIP Craft Beer Upgrade $19.99 Bottom Link -2Bottom Link -1HighlightsDeep-dish Pizza
Gold Coast
Millennium Park
Chicago Riverwalk
Chicago-style Hot Dog
Buckingham Fountain
Gelato
Craft Beer
Lakefront Trail
Oak Street BeachPRICEDiscount Online Rates at $74.99LEVELEasyMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/01/City-Lights-at-Night-walking-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"}Related ToursArrayPrivate Group RequestArray
Kayak & Paddleboard Rentals at Ohio Street Beach
Learn More10:30am - 6:30pm Daily | May-OctoberKayak and SUP rentals on Lake Michigan - single and tandem kayaks available. Paddle past: Ohio Street Bech, The Playboy Building, Navy Pier, The Wrigley Building, Marina City and Chicago Lakefront Trail.
Related ToursStudent / MilitaryKids under 12Kids under 4Students / Seniors 65+Bottom Link -1Bottom Link -2Adult$39.99PRICE$39.99DURATION1 hr - 2hrsCustom Line10:30am - 6:30pm Daily | May-OctoberSCHEDULE10:30am - 6:30pm | May-OctoberAGE4+ (must be 18+ to sign for kayak/SUP)Reserve NowPRICE(Discount Online Rate Includes Kayak/SUP)
Price: Daily 1 Hour Single Kayak/SUP Rental $39.99 2 Hour Single Kayak/SUP Rental $69.99 1 Hour Double Kayak Rental $69.99 2 Hour Double Kayak Rental $129.99 LEVELEasyHighlightsKayak & Paddleboard Lake Michigan with a rental at Ohio Street Beach (next to Navy Pier). Single/tandem kayaks and SUP paddleboards available.LENGTHat your leisureMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2023/02/Bobbys-Bike-Hike-Location-Map.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"}Private Group RequestArray