Bobby's Bike Hike - Chicago Bike, Walking & Food Tours
Bobby's Bike Hike - Chicago Bike, Walking & Food Tours
Discover Lakefront secrets, savor iconic bites, and dive into Windy City history on unforgettable bike, walking & food tours from Navy Pier.
Welcome to Bobby's Bike Hike, where Chicago's vibrant soul comes alive on two wheels, two feet, or a delicious bite at a time. Launching from our prime spot at 540 N Lake Shore Dr, right by the iconic Navy Pier, we've been crafting epic adventures for over a decade. Picture this: crisp Lake Michigan breezes whipping past as you pedal through hidden lakefront neighborhoods, uncovering stories only locals whisper about. Or stroll charming streets, popping into hidden gems for deep-dish bites, gourmet hot dogs, and craft brews that scream authentic Chicago.
Our tours aren't cookie-cutter, they're Bobby's passion poured into every mile. Led by charismatic guides like Gabe, Braeden, and Kevin, who've racked up 4.9 stars from 1,944 rave reviews, you'll laugh, learn, and taste your way through the city's heartbeat. From first-timers out of Dallas gasping 'OMGOSH!' to solo explorers filling solo days with joy, we've created memories that stick. Whether you're chasing skyline views, Chicago's gritty history, or just the best bites off the beaten path, Bobby's Bike Hike turns tourists into temporary locals. Grab a bike, your walking shoes, or your stretchy pants, Chicago's waiting!
Kick off your Chicago adventure with our signature tours that blend motion, flavor, and Windy City magic:
Bikes, Bites & Brews Tour: Pedal 7-10 miles along the lakefront, stopping at neighborhood taverns for craft beers and hearty pub grub. Perfect for groups craving fun and flavor (3-4 hours).
Chicago Food Tour: Walking adventure through River North or Wrigleyville, devouring 6+ tastings, deep-dish pizza, Italian beef, gourmet popcorn. History-packed with zero regrets (2.5 hours).
Lakefront Neighborhoods Bike Tour: Glide past Gold Coast mansions, Lincoln Park beaches, and hidden beaches. Guides share juicy tales of Chicago's elite and underbelly (2 hours).
Signature Walking Tours: Dive deep into architecture, gangland history, or pizza lore without breaking a sweat. All-inclusive bikes, helmets, and snacks provided. Book now, spots fill fast from our Lake Shore Dr HQ!
Take a look at our space and what we have to offer
Don't just take our word for it - hear from our satisfied customers
All tours depart from 540 N Lake Shore Dr, Chicago, IL 60611, right by Navy Pier's south end. Look for our Bobby's Bike Hike flags and friendly guides!
Nope! We provide top-quality hybrid bikes, helmets, locks, and baskets. No experience needed, routes are easy-paced for all fitness levels.
We monitor forecasts closely. Light rain? We go! Heavy weather? Full refunds or reschedule to indoor walking tours. Flexibility is our jam.
Yes! Notify us of allergies/vegetarian/vegan needs 48 hours ahead. We'll swap tastings while keeping Chicago's iconic flavors intact.
Free cancellation up to 24 hours before. Within 24 hours, it's 50% refund. No-shows are tough, so book confidently!
Public tours: 6-12 people for personal vibes. Private tours for 10+ available, corporate events, family reunions, birthdays. Contact us to customize!
Bikes, Bites & Brews for adults; Lakefront Bike Tour for families/kids 12+. All beginner-friendly with stories everyone loves.
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