Experience the vibrant neighborhoods of Chicago on a thrilling bike tour. Discover iconic sights, taste local cuisine, and learn the city’s history from a knowledgeable guide.
Experience the vibrant neighborhoods of Chicago on a thrilling bike tour. Discover iconic sights, taste local cuisine, and learn the city’s history from a knowledgeable guide.
- Lou Malnati’s Pizzeria - AM Day Route and PM Night Route. Experience the unique Chicago-style pizza at one of the city’s most renowned pizzerias. Discover why deep-dish pizza is synonymous with Chicago, explore the establishment’s history dating back to the 1940s, and enjoy intriguing facts about the dish and its origins.
- Gold Coast - AM Day…
- Lou Malnati’s Pizzeria - AM Day Route and PM Night Route. Experience the unique Chicago-style pizza at one of the city’s most renowned pizzerias. Discover why deep-dish pizza is synonymous with Chicago, explore the establishment’s history dating back to the 1940s, and enjoy intriguing facts about the dish and its origins.
- Gold Coast - AM Day Route and PM Night Route. Journey through the city’s most opulent district. Marvel at the magnificent architecture of historic mansions and skyscrapers. Enjoy the lake views and soak in the atmosphere of this historic area.
- Lincoln Park - AM Day Route. Explore the stunning Lincoln Park with its extensive bike trails along Lake Michigan. Delight in the natural surroundings within the bustling city, find sports spots for exercise, and breathe in the fresh air as you prepare for the next culinary adventure. Visit landmarks, starting from the oldest section dating back to 1843 when it was the City Cemetery. Gain more historical insights from your enthusiastic guide as you cycle through the greenery.
- The Wiener’s Circle - AM Day Route. It’s the perfect time to savor Chicago’s most delicious hot dogs. Located in the Lincoln Park neighborhood, it’s an ideal stop to refuel after your ride. Visit the stand to enjoy the classic char-grilled cuisine of Chicago and learn about the unique traditions of the place.
- Bittersweet Pastry Shop & Cafe - AM Day Route. Visit this bakery, renowned for its brownies, and discover why it holds iconic status. The establishment offers high quality at fair prices, so feel free to sample a variety of treats.
- Wrigley Field - AM Day Route. No visit to the Windy City is complete without a tour of Wrigley Field, one of the nation’s oldest baseball stadiums and a popular tourist destination. Use your bike to reach it quickly and enjoyably, gaining new insights from your guide along the way.
- Murphy’s Bleachers - AM Day Route. Continue your culinary journey next to Wrigley Field at this world-famous sports bar and sample the exquisite local craft beer. Immerse yourself in the story of how this place became legendary, its significant impact on the neighborhood, and what sets it apart from others.
- Boystown - AM Day Route. Cycle through the vibrant gay village in the Lakeview neighborhood, one of the largest communities in the US and a cultural hub for residents. It’s renowned for its lively nightlife, welcoming atmosphere, and trendy fashion stores.
- Lake - Be captivated by the stunning views as you cycle along Lake Michigan, one of the five Great Lakes. Feel the energy of the fourth-largest natural freshwater reservoir, steeped in legends and mysterious tales.
- Lakefront Trail - AM Day Route and PM Night Route. Enjoy the 18.5-mile-long shared-use path along Lake Michigan’s shores for a pleasant ride, admiring the beautiful scenes of the shoreline and skyscrapers. The skyline view will accompany you throughout, along with parks, restaurants, bars, stands, gyms, museums, event spaces, a golf course, and more.
- Oak Street Beach - AM Day Route and PM Night Route. This popular Chicago sandy beach attracts around 300,000 visitors during summer weekends. It’s an ideal spot for a sunny day, offering various activities including beach volleyball, bars, sandy shores, and refreshing water. Don’t miss the opportunity to visit.
- North Avenue Beach - AM and PM route. Explore another beautiful and popular beach located in Lincoln Park. Be awed by the breathtaking horizon views, and the multitude of bikers, walkers, and joggers along the Lakefront Trail as you ascend to the beach house’s upper deck.
- Half Acre Beer Company - AM and PM route

- Must see and off the beaten path
- Morning and Evening start times with 2 unique itineraries
- Food and beer samples at two breweries, one bakery, one hot-dog stand and one pizza shop
- Water Bottle
- Bicycle
- Iconic places for selfies
- Helmet
- All Fees and Taxes
- Friendly local guide
- Must see and off the beaten path
- Morning and Evening start times with 2 unique itineraries
- Food and beer samples at two breweries, one bakery, one hot-dog stand and one pizza shop
- Water Bottle
- Bicycle
- Iconic places for selfies
- Helmet
- All Fees and Taxes
- Friendly local guide
- Gratuities
- Gratuities
Embark on an exciting half-day adventure through Chicago’s most fascinating neighborhoods with a personable private guide, experiencing the city from a fresh perspective on a bike ride.
Immerse yourself in the city’s vibrant atmosphere and indulge in tasting Chicago’s most delectable and iconic treats after building up an appetite, all while taking in…
Embark on an exciting half-day adventure through Chicago’s most fascinating neighborhoods with a personable private guide, experiencing the city from a fresh perspective on a bike ride.
Immerse yourself in the city’s vibrant atmosphere and indulge in tasting Chicago’s most delectable and iconic treats after building up an appetite, all while taking in the city’s unique beauty.
Explore more sights in less time by cycling
Savor the true essence of the City by the Lake with recommendations from a local guide
Uncover iconic neighborhoods and enjoy engaging historical insights.
Gain knowledge about the distinct characteristics of local cuisine and its origins.
- If you have dietary restrictions, please add a note in the special requirements section when booking
- Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
- Minimum age is 16 years
- Operates rain or shine, please dress appropriately
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.