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Explore Chicago on Two Wheels with Bobby's Bike Hike

Experience Chicago’s vibrant culture and stunning landscapes on guided bike, walking, and food tours with Bobby's Bike Hike.

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Discover the vibrant city of Chicago like never before with Bobby's Bike Hike. Offering bike, walking, and food tours, it's the perfect way to experience the Windy City.

A brief summary to Bobby's Bike Hike - Chicago Bike, Walking & Food Tours

  • Monday 9 am-6:30 pm
  • Tuesday 9 am-6:30 pm
  • Wednesday 9 am-6:30 pm
  • Thursday 9 am-6:30 pm
  • Friday 8:30 am-6:30 pm
  • Saturday 8:30 am-6:30 pm
  • Sunday 8:30 am-6:30 pm

Local tips

  • Book your tour in advance to secure your spot, especially during peak tourist seasons.
  • Arrive early to ensure you have time to select the perfect bike and get fitted comfortably.
  • Wear comfortable clothing and sturdy shoes to enhance your biking experience.
  • Don’t forget your camera to capture the stunning views along the Lake Shore and the city’s skyline.
  • Consider joining a food tour to taste authentic Chicago-style dishes like deep-dish pizza and hot dogs.
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Getting There

  • Public Transit

    From Berwyn, walk to the Berwyn Metra Station located at 6820 Windsor Ave. Take the Metra train towards Chicago Union Station. After approximately 30 minutes, disembark at the Union Station stop. Once at Union Station, exit the building and head to the Canal Street exit. From there, you can catch the CTA 'Pink Line' train. Board the Pink Line towards 18th Station and ride for about 10 stops. Disembark at the Damen stop. Transfer to the CTA 'Blue Line' train, which is just a short walk away. Board the Blue Line towards O'Hare and ride for 6 stops. Get off at the Washington stop. Finally, transfer to the 'Red Line' train towards Howard, and ride for 2 stops to the Grand stop. From the Grand stop, exit the station and walk east on Grand Avenue for about 0.5 miles until you reach 540 N Lake Shore Dr, where Bobby's Bike Hike is located.

  • Biking

    If you're feeling adventurous and would like to bike, you can rent a bike from a local rental shop in Berwyn. Start by heading towards the Salt Creek Trail, which is a scenic route. Follow the trail north until you reach the Chicago River. Continue along the river until you reach Lake Shore Drive. Once you are at Lake Shore Drive, head south on the bike lane until you arrive at 540 N Lake Shore Dr, where Bobby's Bike Hike is located. The total biking distance is approximately 12 miles and should take around 1 hour.

  • Walking

    For those who prefer to walk, start at the Berwyn Metra Station. Walk east on Windsor Avenue until you reach the intersection with Ogden Avenue. Turn left and walk north on Ogden Avenue until you reach the CTA 'Pink Line' station at 18th Street. Board the Pink Line towards 18th Station and get off at the Damen stop. Walk a few blocks to the Blue Line station and board the Blue Line towards O'Hare. Get off at the Washington stop. From there, transfer to the 'Red Line' train towards Howard and get off at the Grand stop. Walk east on Grand Avenue for about 0.5 miles to 540 N Lake Shore Dr, where Bobby's Bike Hike is located. The total walking distance is approximately 15 miles and may take around 5 hours.

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Discover more about Bobby's Bike Hike - Chicago Bike, Walking & Food Tours

Bobby's Bike Hike is your gateway to exploring the bustling streets and stunning landscapes of Chicago. Nestled along the scenic Lake Shore Drive, this tour operator specializes in bike, walking, and food tours that cater to all levels of adventurers. With a fleet of high-quality bicycles available for rent, you can navigate through the city's iconic neighborhoods, picturesque parks, and along the breathtaking waterfront at your own pace. Whether you’re a local or a visitor, Bobby's provides a unique perspective on Chicago's rich history and vibrant culture. The guided tours offered by Bobby's Bike Hike are designed to showcase the best of the Windy City. Join a knowledgeable tour guide who will lead you through famous landmarks, hidden gems, and culinary hotspots. Sample delicious dishes from local eateries while enjoying a leisurely ride through the city’s most picturesque routes. The tours are not just about cycling; they also incorporate walking segments, allowing you to immerse yourself fully in the sights and sounds of Chicago. Accessibility is a priority at Bobby's, with options for all ages and fitness levels. Whether you're interested in a leisurely afternoon ride or an exciting food adventure, there’s something for everyone. Rent a bike for a self-guided exploration, or join a group tour to discover the city alongside fellow travelers. With its friendly staff and commitment to providing unforgettable experiences, Bobby's Bike Hike promises an exciting and engaging way to see Chicago. Grab your helmet and get ready to pedal through the heart of this vibrant metropolis!

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