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Discover Chicago on a 4-hour bike tour featuring iconic neighborhoods, delicious food stops including pizza, hot dogs, cupcakes, and beer, led by friendly local guides.

The Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes, and Beer offers an engaging way to see the city’s most interesting neighborhoods while sampling some of its best-loved foods. Priced at $179 per person, this half-day adventure lasts approximately 4 hours and includes a bike, helmet, and water bottle for each participant. With two unique itineraries (morning and evening), the tour provides a flexible opportunity to enjoy Chicago from a local perspective.
This tour is ideal for those who enjoy active outings combined with culinary treats. It’s suitable for anyone with moderate physical fitness, and it’s a fantastic choice for travelers eager to explore both famous sites and off-the-beaten-path spots. The small group size, capped at 15 travelers, ensures a friendly, personalized experience. A key highlight is the inclusion of food and beer samples at several stops, making it a well-rounded day of sightseeing and tasting.
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The tour begins at Bobby’s Bike Hike – Chicago Bike, Walking & Food Tours, located at 540 N Lake Shore Dr. This central location makes it easy to access via public transportation. Start times are at 11:30 am, and the tour ends back at the same meeting point, simplifying planning for the day.

The Gold Coast is one of the tour’s key stops, where riders admire spectacular architecture of historic mansions and modern high-rises. The guide explains the history behind these buildings and offers great views of Lake Michigan. The 10-minute stop provides an excellent photo opportunity and a chance to appreciate Chicago’s wealth and design elegance.

At Lincoln Park, the tour offers a 15-minute break to explore bike trails along Lake Michigan. The park’s natural environment offers a peaceful contrast to the urban landscape, with chances to see sports fields and open green spaces. It’s a great place for a quick breather and some scenic photos amidst the city’s greenery.

In the Lincoln Park neighborhood, The Wiener’s Circle is a well-known hot dog stand. The tour includes a 10-minute stop for tasting Chicago’s iconic hot dogs, renowned for their unique toppings and flavor. This stop complements the city’s culinary reputation and offers a satisfying bite after some cycling.
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A 20-minute visit to the Bittersweet Pastry Shop & Cafe lets participants sample their celebrated brownies and other baked goods. This bakery is recognized for its high quality and fair prices, making it easy to try several treats. It’s a perfect sweet pause during the ride.

The tour includes a quick ride to Wrigley Field, one of the oldest and most famous baseball stadiums in the country. The 10-minute stop allows for photos and an appreciation of Chicago’s sports culture. No tickets are included, but the exterior and surroundings are captivating sights.

Next, a 20-minute stop at Murphy’s Bleachers, a renowned sports bar right next to Wrigley Field, offers a taste of Chicago’s craft beer scene. The guide shares stories about the bar’s history, and visitors get to enjoy a delicate local brew as part of the experience.
The Lakeview area features the gay village, famous for its vibrant nightlife and active community. A short stop lets riders take in the lively atmosphere and colorful streets, adding a cultural flavor to the tour.
One of the tour’s highlights is riding along Lake Michigan for 15 minutes, absorbing views of the vast freshwater lake. The energy and legends associated with this fourth-largest freshwater body make this a memorable part of the day.
The 20-minute ride on the Lakefront Trail offers panoramic scenes of the shoreline and city skyline. This scenic path is perfect for photography and enjoying Chicago’s open-air beauty from a bicycle perspective.
The tour visits Oak Street Beach and North Avenue Beach, both popular spots in Lincoln Park. Each offers spectacular views and space to relax or take photos. The 30-minute stop at North Avenue Beach allows for enjoying the sand and the lively summer scene. These beaches are among Chicago’s top spots for sunbathing and people-watching.
The day concludes with a 30-minute visit to Half Acre Beer Company, where guests can enjoy another local craft beer. The brewery’s relaxed atmosphere makes it a fitting ending for this engaging, food-filled bike tour.
The tour operates rain or shine, so dressing appropriately is essential. It is suitable for those with moderate physical activity levels, given the 4-hour duration and bike riding component. The meeting point is easily accessible near public transportation, and the tour is limited to 15 participants for a more personalized experience.
All bikes, helmets, and water bottles are included, ensuring comfort and safety. Food and beer samples are provided at two breweries, a bakery, a hot-dog stand, and a pizzeria, giving a diverse taste of Chicago cuisine.
The combination of cycling through iconic neighborhoods, sampling local foods and beers, and visiting historic and cultural sites makes this tour stand out. The two different itineraries allow for a variety of experiences, whether you opt for the morning or evening tour. The friendly guides add a personal touch, sharing stories and insights about Chicago’s architecture, history, and culinary traditions.
This 4-hour biking experience offers an excellent balance of physical activity, sightseeing, and culinary delights. It’s perfect for active travelers who want to see more than just the typical tourist spots and enjoy a taste of Chicago’s rich food scene. The small group size and well-planned stops ensure a relaxed pace and enjoyable atmosphere.
While the tour focuses on popular landmarks and local eats, it’s also accessible enough for most with moderate fitness levels. The inclusion of food and drink samples at multiple stops makes it a great value for the price, especially for those eager to combine sightseeing with authentic Chicago flavors.
“My husband and I thoroughly enjoyed the tour of Chicago by bike. It is such a fun way to see the city. I highly recommend going on this tour, even …”
Is this tour suitable for children?
The minimum age is 16 years, making it suitable for older teenagers and adults interested in active sightseeing.
What should I wear for the tour?
Since the tour operates rain or shine, dress appropriately for the weather, and wear comfortable clothing suitable for cycling.
Are dietary restrictions accommodated?
The tour can accommodate vegetarians or those avoiding beef or pork, but it has limited options for gluten-free or vegan diets.
What do I need to bring?
All necessary gear like bikes, helmets, and water bottles are provided. Just bring personal items, weather-appropriate clothing, and an appetite for Chicago’s foods.
Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour, allowing for a full refund.