Day 1

First Steps in Chicago & Sunset Over the Skyline

Welcome to Chicago, the “Windy City”! You’ve arrived in the vibrant capital of the Midwest, where towering skyscrapers, music, and culture blend seamlessly with the excitement of travel. This first day, entirely at your leisure, is the perfect opportunity to soak up the American atmosphere.

Upon arrival, make your way to your hotel, ideally located in the heart of the city, just steps from the main shopping avenues and the shores of Lake Michigan.

As evening approaches, enjoy a spectacular 360° experience. Your ticket, booked for sunset, grants you access to the observation deck on the 94th floor of the John Hancock Center, offering breathtaking panoramic views over Lake Michigan and Chicago’s iconic skyline.

A signature cocktail awaits you at the 94th-floor bar, providing a stylish yet relaxed moment to celebrate your arrival in the United States. Plan to spend approximately 1.5 to 2 hours on-site to fully enjoy the stunning scenery.

For thrill-seekers, the optional Tilt Experience (available at an additional cost on-site) offers a heart-racing attraction that literally tilts you out over the city!

Want to extend the evening? Chicago is considered the world capital of the blues, and several legendary blues clubs are located just a short walk from your hotel. A selection of recommended blues clubs can be found in your travel guide.

Day 2

Authentic America Immersion & the Harley-Davidson Legend

This morning, board the train from Chicago to Milwaukee. As you travel through the Midwest, enjoy views of charming rural stations, golden fields, and typical small-town America unfolding outside your window. Welcome to authentic America.

Upon arrival in Milwaukee, discover the legendary Harley-Davidson Museum, a true shrine to American motorcycling. From the very first models built in 1903 to today's iconic machines, each gallery tells the story of more than a century of innovation, freedom, and adventure. The collections, fascinating anecdotes, and unique atmosphere immerse both enthusiasts and newcomers in the legendary world of Harley-Davidson.

After your visit, enjoy lunch at the museum's restaurant (not included, payable on-site) and soak up the authentic American atmosphere.

In the late afternoon, return by train to Chicago and rediscover the vibrant energy of the city. Enjoy your final evening at leisure.

Day 3

Chicago like a local

Before hitting the road, experience Chicago like a local! This morning, explore the city with a French-speaking expatriate who has been living here for several years and is passionate about its history and extraordinary architecture. Through her stories, insider tips, and local perspective, you'll discover the Windy City from a different angle.

Your walking tour takes you through the Loop District, the vibrant heart of Chicago and a true open-air architectural museum. Walk beneath the city's famous elevated train tracks, one of Chicago's most iconic symbols, before heading to State Street and the legendary Chicago Theatre, instantly recognizable by its giant red marquee.

Continue along the Chicago Riverwalk, a must-see promenade offering spectacular views of some of the city's most iconic buildings, including the Wrigley Building, Tribune Tower, and the twin towers of Marina City.

Duration: approximately 3 hours.

At 1:00 PM, enjoy lunch at a panoramic restaurant carefully selected by Planet Ride. Savor your meal (not included, payable on-site – allow approximately $30 to $40 per person) while taking in breathtaking views of Chicago.

At the end of the afternoon, return to your hotel.

At 4:00 PM, meet in the hotel lobby for the road trip briefing. This is the perfect opportunity to meet your guide, get to know your fellow riders, and prepare together for the adventure ahead!