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Looking for an adventure that’s beyond the ordinary? The American Riders bring you an electrifying way to explore the Windy City—on a vintage-inspired sidecar motorcycle! This isn’t your average sightseeing trip; it’s an immersive, adrenaline-pumping journey through the heart of Chicago, where history, culture, and adventure collide.
The American Riders offer a one-of-a-kind sidecar motorcycle Chicago tour ride that takes you on an unforgettable 90-minute adventure through the city’s most iconic landmarks. Whether you’re a first-time visitor or a local looking for a fresh perspective, our expertly curated route showcases Chicago like never before.
Ride through the city’s architectural marvels, feel the energy of its vibrant streets, and capture picture-perfect moments—all from the comfort of a retro-styled motorcycle sidecar!
A stunning view of the skyline and Lake Michigan.
Home of the legendary Chicago Cubs.
A cinematic backdrop featured in Hollywood blockbusters like Batman Begins and The Dark Knight.
Ride through Chicago’s premier shopping and cultural district.
Snap an unforgettable selfie at this world-famous landmark.
A thrilling ride along Chicago’s vibrant waterfront.
Get ready to see Chicago from a whole new perspective! Our guided tours cater to thrill-seekers, history buffs, and urban explorers alike.
Not your typical Chicago bike ride tour—this is adventure redefined!
Five designated stops at prime Chicago locations for photo ops and storytelling.
Designed for all riders, including those with mobility challenges.
Personalized experience with a maximum of two riders per bike.
Every ride includes professional videos and photos.
Get ready to see Chicago from a whole new perspective! Our guided tours cater to thrill-seekers, history buffs, and urban explorers alike.
Not your typical Chicago bike ride tour—this is adventure redefined!
Five designated stops at prime Chicago locations for photo ops and storytelling.
Designed for all riders, including those with mobility challenges.
Personalized experience with a maximum of two riders per bike.
Every ride includes professional videos and photos.
The American Riders take you on a Chicago bike tour like no other. Riding in a vintage-style chopper sidecar isn’t just about sightseeing—it’s about feeling the rush of the open road while exploring a city full of history and energy.
Every tour includes professional bike rentals in Chicago with mounted Insta360° cameras to capture stunning 360-degree videos and photos of your journey. Share your ride with the world!
We’ve hand-picked a Chicago bike ride tour route that takes you to some of the city’s most breathtaking locations, allowing you to immerse yourself in its culture and beauty.
We believe adventure is for everyone! Our motorcycles are specially equipped to accommodate guests with mobility challenges, ensuring a comfortable and exciting experience for all.
Enjoy a personalized playlist as you cruise through the city, making every moment more thrilling!
Opt for a special food tour edition and enjoy Chicago’s best local eats along the ride!
The American Riders take you on a Chicago bike tour like no other. Riding in a vintage-style chopper sidecar isn’t just about sightseeing—it’s about feeling the rush of the open road while exploring a city full of history and energy.
We’ve hand-picked a Chicago bike ride tour route that takes you to some of the city’s most breathtaking locations, allowing you to immerse yourself in its culture and beauty.
We’ve hand-picked a Chicago bike ride tour route that takes you to some of the city’s most breathtaking locations, allowing you to immerse yourself in its culture and beauty.
We believe adventure is for everyone! Our motorcycles are specially equipped to accommodate guests with mobility challenges, ensuring a comfortable and exciting experience for all.
Enjoy a personalized playlist as you cruise through the city, making every moment more thrilling!
Opt for a special food tour edition and enjoy Chicago’s best local eats along the ride!
The only sidecar motorcycle Chicago tour ride offering an exhilarating way to explore the city.
Our local riders know Chicago inside and out, bringing history and culture to life.
Small group sizes make for a more intimate and immersive adventure.
Helmets, protective gear, and top-tier safety protocols ensure a smooth ride.
With six tours daily, you can pick a time that fits your itinerary.
Just $150 per motorcycle, making it a budget-friendly way to experience an unforgettable ride.
Whether it’s a date night, family outing, or solo adventure, we’ve got you covered.
The only sidecar motorcycle Chicago tour ride offering an exhilarating way to explore the city.
Our local riders know Chicago inside and out, bringing history and culture to life.
Small group sizes make for a more intimate and immersive adventure.
Helmets, protective gear, and top-tier safety protocols ensure a smooth ride.
With six tours daily, you can pick a time that fits your itinerary.
Just $150 per motorcycle, making it a budget-friendly way to experience an unforgettable ride.
Whether it’s a date night, family outing, or solo adventure, we’ve got you covered.
Have questions you want answers to?
Our tours last 90 minutes, giving you ample time to enjoy Chicago’s top sights without feeling rushed.
Absolutely! We welcome riders of all ages, and our sidecars are built for comfort and safety.
Yes! You can book a solo ride or bring a companion. Each motorcycle can accommodate up to two riders.
Nope! Our tours are guided, and you’ll be a passenger, so no license is required.
Our motorcycles comfortably fit most passengers, but if you have specific concerns, feel free to reach out.
Dress comfortably and according to the weather. Helmets and safety gear will be provided.
We ride rain or shine! In case of severe weather, we’ll reschedule or issue a refund.
Our adventure begins at 110 Roosevelt Rd, Chicago, IL 60605.
Yes! While we provide professional 360-degree footage, you’re welcome to capture your own moments.
Yes! Contact us for customized group or private tours tailored to your preferences.
Riding through Chicago on a vintage chopper was beyond exhilarating. The sidecar was super comfy, and the personalized tour made it feel like a VIP experience. Highly recommend American Riders!
I’ve always wanted to ride a classic motorcycle, and this tour exceeded my expectations. From the breathtaking views to the edited video we got at the end, everything was perfect.
Exploring Chicago on these incredible WWII bikes was like stepping back in time. The 360° video we received was the cherry on top. A must-do for anyone visiting the Windy City!
As a Chicago native, I thought I’d seen it all, but American Riders showed me a side of my city I never knew existed. Truly unforgettable.
Stay tuned for exciting updates, travel guides, and behind-the-scenes stories from our epic rides through Chicago!
Ready to experience The American Riders? Book your ride today and discover Chicago in a way you never imagined!
