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Image by Sawyer Bengtson

A Weekend in Chicago

This cosmopolitan playground is bursting with things to do. Sightseeing options range from Chicago icons like Millennium Park’s sculptures, fountains, gardens and event spaces to awe-inspiring architecture by Frank Lloyd Wright, Frank Gehry, Daniel Burnham and Louis Sullivan. Take in the beautiful cityscape with a stroll along the Chicago Riverwalk, where you can enjoy a waterside meal, sip a drink or set out on an architecture cruise on the Chicago River.



Trip Infos

  • Luxury city break, ideal for Art & Architecture enthusiastic 

  • Enjoy a Private Discovery of the Art Institute & a private before hours discovery of the MCA

  • Cruise privately the Chicago river and be amazed by the architecture

  • Enjoy at Jazz immersion at an intimate Diner show

Duration:  4 Days / 3 Nights 


  • Day 1-4: Chicago - The Peninsula

Estimated Price: $4,400 per person

(Based on 2 Adults / Private Activities)



Welcome to Chicago ! Upon arrival, meet your chauffeur and ride privately to your hotel. 

There it is: the famous Chicago skyline set against the sweeping shore of Lake Michigan. You’ll quickly appreciate this urban-meets-natural beauty when your feet hit the ground in the nation’s third-largest city. In the heart of the Midwest, Chicago boasts soaring skyscrapers, 77 colorful neighborhoods, 42 kilometers of lakefront with 26 beaches and 580 parks and green spaces. Equally impressive are the dining options – 7,300 restaurants and more than 65 craft breweries – outstanding arts and culture, urban recreation along the waterfront, world-famous events and a vibrant LGBTQ+ scene. 

Night at: Peninsula Chicago - Grand Deluxe King



This morning, celebrate the Art during a private pre-0pening discovery of the MCA. Boldly interweaving exhibitions, performances, collections, and educational programs, the MCA is an innovative and compelling center of contemporary art where the public can directly experience the work and ideas of living artists, and understand the historical, social, and cultural context of the art of our time.

This Afternoon, celebrate the Architecture aboard a private boat on the Chicago river; It is the sweet, simple things of life which are the real ones after all. Chicago is legendary for its architecture. Highly trained and passionate volunteer docents provide a detailed narrative of Chicago's various architectural styles and the stories of the people who designed and built the city.

Night at: Peninsula Chicago - Grand Deluxe King

Image by Chris Bair


Today, enjoy a privately guided discovery of the world famous Art Institute of Chicago.

Experience the greatest Impressionist collection outside Paris, and view contemporary masterpieces in the spectacular Modern Wing.

Tonight, enjoy a intimate atmosphere at Le Piano for an unforgettable Jazz night. Le Piano is truly a hidden gem with Bohemian Parisian influences, tucked away in the Rogers Park neighborhood. With a listening room designed around a magnificent grand piano where intimate performances are featured every evening by Chicago’s finest jazz musicians, it is an experience quite like no other.

Night at: Peninsula Chicago - Grand Deluxe King

Image by Pedro Lastra


After a morning at leisure, enjoy a private transfer back to the airport before flying to your next destination. 

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