This exclusive Chicago experience offers private transfers, guided tours, and luxury dining. From panoramic city views at 360 Chicago Observatory to a private architecture river cruise and visits to top landmarks like Millennium Park, Willis Tower Skydeck, and Lincoln Park Zoo, each day combines cultural exploration with unforgettable sights.
Daily
Trip Includes
This itinerary includes daily breakfasts and three expertly selected dinners, giving you the perfect balance of guided experiences and free time for lunch to discover the city's vibrant food scene on your own.
Trip Excludes
Prices are from per person based on twin/double share accommodation, subject to availability and current exchange rates, based on a minimum of 20 passengers, pricing reflects departure date of October 2025
Arrive in Chicago and enjoy a seamless journey with our exclusive private transfer service from the airport to your chosen hotel. Relax and unwind as you settle in. In the evening, your private transfer will take you to 360 Chicago Observatory, where you’ll be treated to stunning panoramic views of the Windy City. Witness Chicago's glittering skyline from the iconic John Hancock Building. End the day with a welcome dinner at one of Chicago’s finest restaurants, savoring local specialties in a vibrant atmosphere.
Just steps away from renowned Rush Street, this luxurious hotel offers stylish accommodations with luxury amenities, modern event facilities, irresistible dining options and gracious service. This is the best destination in downtown Chicago for shopping, dining and business, being just a short journey away from Chicago's finest attractions, including Water Tower Place, Michigan Avenue, John Hancock Tower and Navy Pier. The hotel is also ideally situated for museum visits, as the Museum of Contemporary Art and the Art Institute of Chicago are just a short walk away. This property accommodates a range of meetings, events and social gatherings every year, boasting a staggering 5,480 square metres of flexible function space. The famed Crystal Ballroom features a built-in illuminated dance floor, and from its graceful balcony to its crystal chandeliers, many a prominent wedding reception has been held here. Additional $20 extra person fee for guests older than 13 years old.
Begin your day with a delicious breakfast at your hotel, preparing you for a full day of exploration. Meet your expert local guide for a Panoramic Private Tour of Chicago, visiting Millennium Park and Navy Pier, with special stops at Cloud Gate and Crown Fountain. Hop aboard the Loop train for a unique ride through the heart of the city, followed by a visit to the University of Chicago campus and a scenic drive along the Lakefront Trail. Lunch will be on your own at one of the city's many fantastic options. In the afternoon, enjoy a Private Architecture River Tour, discovering over 40 iconic landmarks. Cap off the day with a lovely dinner at another of Chicago’s acclaimed eateries.
Meal
After a hearty breakfast, embark on a Private Architecture Tour, where you’ll explore Chicago’s diverse architectural styles, from Neo-Classical to Art Deco. Visit the Art Institute of Chicago with your guide, home to a world-class collection of Impressionist, Asian, and modern art. Lunch is on your own, allowing you to choose from a variety of excellent restaurants near the museum. In the afternoon, visit the Willis Tower Skydeck for an exhilarating view of the city from 103 floors up. Dinner will be at your leisure, giving you the freedom to explore Chicago’s rich culinary scene.
Meal
Start your day with a satisfying breakfast before heading to the Lincoln Park Zoo, one of the nation’s best free zoos. Your guide will share insights about the animals and the zoo’s conservation efforts. Afterward, visit the beautiful Lincoln Park Conservatory, where you’ll enjoy the serene atmosphere and exotic plant displays. Lunch is on your own, perhaps at a charming spot within Lincoln Park. Enjoy your final dinner at a top Chicago restaurant, indulging in a memorable meal that captures the essence of the city’s diverse cuisine.
Meal
Enjoy a relaxed morning breakfast at the hotel and take some time for last-minute shopping or sightseeing. Your private transfer will then take you to the airport for your departure, ensuring a smooth and stress-free end to your exclusive Chicago experience.
Meal
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