Chicago Essentials

Day 1

First Glimpses of Chicago’s 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.

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Day 2

Local Immersion in the Heart of the Windy City

Before hitting the road, experience Chicago like a local! This morning, discover the city alongside a French-speaking expatriate who has been living here for several years and is passionate about its history and remarkable architecture. Through her stories, insights, and local recommendations, you’ll see the “Windy City” from a unique perspective.

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

You’ll then continue along the Chicago Riverwalk, a must-see promenade offering spectacular views of the city’s most famous landmarks, including the Wrigley Building, Tribune Tower, and the twin towers of Marina City.

Duration: approximately 3 hours.

At 1:00 PM, enjoy a well-deserved lunch break 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 over Chicago.

In the late 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!

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