Our Journeys

Long Weekend in Chicago

$1,850 USD

Long Weekend in Chicago

Four days in Chicago, the windy city.


DAY 1 - December 3 - Thursday - An introduction to Chicago

Upon arrival, guests should make their way to the hotel in the city center. Time permitting, we may fit in a short city center walking tour. If not, we will instead meet for drinks, welcome conversation and dinner. Night in Chicago

DAY 2 - December 4 - Friday - AIC and Millenium Park

Friday morning we will visit the world-renowned Art Institute of Chicago, the second largest museum in the nation. Among all it has to offer, the museum features a collection of Impressionist and Post-Impressionist art in its permanent collection. There is truly something for all artistic tastes! After the visit, group members will have lunch independently. Friday afternoon we will explore Millenium Park: A lively and spectacular gathering spot located in the heart of Chicago that attracts locals and visitors alike. We will enjoy some free time before heading to a very special group dinner. Night in Chicago

DAY 3 - December 5 - Saturday - The Chicago River, shopping and the theatre

Saturday morning we will board Chicago’s First Lady for a 90-minute river tour presented by the Chicago Architecture Foundation (weather permitting). A knowledgeable guide will bring the cityscape to life and reveal how Chicago grew from a small back-country outpost into one of the world’s most important crossroads in less than 100 years. We will then stop for lunch and head towards The Magnificent Mile District to enjoy Chicago’s greatest shopping experience. This area is world famous not only for its abundance of luxury boutiques and unique stores but also for cultural events, live music, museums, sports and theatrical performances. Whether you enjoy simply strolling and sightseeing or are a shopping lover, you will find this street of great interest. Saturday night we will venture to the theatre for a wonderful performance. Night in Chicago

DAY 4 - December 6 - Sunday - Museum Campus

Sunday morning we will head to Museum Campus, a 57-acre park that surrounds three of the city’s most renowned museums, all dedicated to natural sciences. The park also hosts Soldier Field, the oldest NFL stadium and home of the Chicago Bears. We will have some time to visit a museum or to stroll around this green space and enjoy the city views, watch the sailboats on Lake Michigan and admire the outdoor sculptures that dot the area. We will stop for lunch before guests are transported to the airport for departing flights home.


What is included in the trip

  • Lodging in double room
  • On-trip transportation

What is not included

  • International airfare to and from Chicago
  • Personal expenses
  • Travel Insurance
  • Tips for drivers and guides


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    The Customized Journeys Team