Unforgettable Small Group Biking Tours from Chicago to Milwaukee

Unforgettable Small Group Biking Tours from Chicago to Milwaukee

If you’re looking to combine active adventure with cultural exploration, this small group biking tour from Chicago to Milwaukee offers a unique way to see the Great Lakes region. It’s perfect for those who love cycling, discovering off-the-beaten-path sights, and enjoying local food and drinks without the hassle of planning every detail. With just 8 travelers on each trip, it promises intimacy, personalized attention, and memorable moments along the way.

What we really love about this tour is the blend of scenic lakefront riding, visits to iconic landmarks, and the chance to enjoy Milwaukee’s vibrant city life afterward. Plus, the fact that it’s designed for a moderate fitness level means it’s accessible for most cyclists. One thing to keep in mind is the distance and terrain—it’s mostly flat but expect some headwinds, especially along the lake. This tour suits active travelers who want a day packed with adventure, cultural insights, and good eats.

Good To Know

• Well-balanced itinerary with a mix of scenic rides, cultural visits, and local dining
• Small group size for a more personalized and engaging experience
• Comfortable logistics including hotel stay, meals, and safety support
• Moderate difficulty level, suitable for most cyclists with some fitness
• Cultural highlights like the Bah temple, Milwaukee Art Museum, and local neighborhoods
• Focus on authentic experiences and delicious food, especially Milwaukee’s renowned breweries and eateries

A Practical Guide to the Chicago to Milwaukee Bike Tour

This tour, operated by Green Path Pedals, offers a thoughtfully curated experience that balances active cycling with sightseeing and city exploration. Starting early at 7:00 am from Chicago’s Wolfram Street, it’s a full day that stretches into late afternoon, giving you plenty of time to absorb both cities’ atmospheres.

The Route and Terrain
Covering roughly 74.6 miles with a gain of +963 ft and descent of -1,058 ft, the ride mostly involves flat terrain. The roads are predominantly paved (79%) with some trail sections (21%), making it manageable for most riders. The route shifts between suburban areas and secluded bike paths, perfect for avoiding heavy traffic while enjoying nature. Expect some southward lake winds, which can add a bit of resistance but also bring refreshing breezes.

What you’ll see and do
The ride begins with a scenic cruise along the Chicago lakefront trail, which is widely praised for its stunning views of Lake Michigan and the city’s skyline. As you pedal southward, you’ll pass notable landmarks like the Home Alone house, a treat for movie fans, and the Bah temple, which is the only Bahá’í place of worship in North America and listed on the National Register of Historic Places—an unexpected cultural gem on your route.

Midway, you’ll arrive in Kenosha, where you’ll stop for lunch at Anna’s on the Lake, a highly recommended local restaurant with great reviews for its fresh seafood, salads, and relaxed vibe. Riders have full control over the frequency of rest stops, allowing for a comfortable pace tailored to your group’s needs.

Safety and logistics
Every rider is responsible for bringing their own biking gear, but a bike pump is provided at the pickup point to help with any last-minute adjustments. The tour includes a safety vehicle and route planning to ensure smooth navigation and emergency support. The small size of the group means you’ll get plenty of individual attention, and the guide is known for sharing insightful stories and local tips, making the ride more engaging.

Evening in Milwaukee
Upon arriving in Milwaukee at the Hilton Milwaukee, you’ll have time to shower, relax, and prepare for dinner. The hotel’s location makes exploring the city easy. The evening includes a dinner in Milwaukee, giving you a chance to taste local flavors, perhaps with some of Milwaukee’s famous brews or hearty American fare.

The next day kicks off with a hotel breakfast before a guided tour of Milwaukee’s top attractions. You’ll visit City Hall, stroll through the Historic Third Ward, and enjoy lunch at the trendy Blue’s Egg, known for its creative brunch and lunch options. Free time after lunch allows you to explore the city’s breweries, museums, or just soak in the local vibe.

Return to Chicago is by car, with pickup between 4-5 pm, giving you a comfortable window to wind down and reflect on your weekend adventure.

What’s Included and What’s Not

You’ll appreciate that the tour’s price of $349 per person provides a solid value considering the lodging, meals, transportation, and guided tour included. The package covers dinner in Milwaukee, lunch at Anna’s, breakfast at the hotel, and a city tour. A bike pump at the start ensures your bike is ready to go, and the air-conditioned vehicle makes the journey back comfortable.

However, cyclists need to bring their own biking gear. This might seem like a small detail, but it’s worth noting since comfort and safety are paramount on such a long ride.

The Experience: Pros and Cons

What travelers love is the combination of stunning lakeside views with cultural stops like the Bah temple and Milwaukee museums. The thoughtful pacing and small group size mean everyone can enjoy the ride without feeling rushed or overwhelmed. Reviewers mention the delicious food—from lunch at Anna’s to dinner and brunch—highlighting how well the meals complement the overall experience.

On the flip side, some riders might find the distance challenging if they’re new to biking or prefer shorter rides. The headwinds along the lake are a natural part of the experience but could be tiring if the weather is windy. Also, since the tour depends on good weather, any rain or storms could lead to rescheduling or cancellations, with clear policies for refunds or rescheduling.

Final Thoughts: Is This Tour for You?

This small group biking tour is perfect for active travelers who want a relaxed yet engaging way to explore both Chicago and Milwaukee. It offers a blend of scenic riding, cultural discoveries, and delicious local food that appeals to those seeking a well-rounded weekend adventure. The small group size fosters camaraderie, while the comprehensive itinerary ensures you see the best of both cities.

It’s especially suited for cycling enthusiasts with moderate fitness levels who enjoy a mix of outdoor activity and urban exploration. If you’re someone who appreciates authentic experiences—from passing by historic landmarks to sampling Milwaukee’s famous brews—this tour will deliver.

While the price is reasonable considering the included accommodations, meals, and guided elements, keep in mind that biking gear is not provided. Travelers should be comfortable on a bike and prepared for a full day on the move. Those who prefer a more leisurely pace or shorter rides might want to consider alternative options, but for those ready for an active and scenic weekend, this experience offers a memorable journey.

FAQ

• What is the starting point for the tour? The tour begins at 1719 W Wolfram St, Chicago, IL 60657, at 7:00 am.
• How long does the tour last? The trip runs for about 1 day and 10 hours, including cycling, sightseeing, and meals.
• What is the total distance? Riders will cover approximately 74.6 miles during the day.
• What should I bring? You need to bring your own biking gear, including helmet, gloves, and appropriate clothing.
• Is the route suitable for all fitness levels? The tour is designed for those with moderate physical fitness; it involves mostly flat terrain but includes some wind resistance.
• Are meals included? Yes, meals include lunch at Anna’s, dinner in Milwaukee, and breakfast at the hotel on Sunday.
• Can I cancel if the weather is bad? Yes, the tour has a flexible cancellation policy, and trips canceled due to bad weather will be fully refunded or rescheduled.
• What if I need assistance during the ride? A safety vehicle is on route to support riders if needed.
• How do I get back to Chicago? Return is by car, with pickup scheduled between 4-5 pm on Sunday.

Final Words

This Chicago-to-Milwaukee bike tour offers a fantastic way to combine exercise, sightseeing, and local culture—all in one memorable weekend. It’s best suited for travelers who enjoy active pursuits and want a guided, small-group experience that emphasizes comfort, safety, and authentic discoveries. The thoughtfully planned itinerary, combined with the stunning scenery and delicious food, makes it a worthwhile choice for those looking to enjoy the region’s highlights without the stress of planning every detail.

Whether you’re a seasoned cyclist or a passionate beginner, this tour caters to a wide range of fitness levels and interests, making it a great option for anyone eager to explore Wisconsin’s charming city. Just remember to pack your biking gear and a sense of adventure—you’re in for a ride to remember.