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Gems of Chicago Sample Itinerary

3 DAYS
Chicago, Illinois, United States
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Chicago is well known for its art, architecture and beautiful lakeside location. During this quick trip to the windy city you will see some of its famous sites while also getting off the beaten path to discover some of its hidden gems.

  • Day 1: Arrivals

    • Breakfast

      On Own

    • AM Activity

      Art History at the Art Institute Experience all of the highlights of one of the oldest and largest art museums in the country. Built in 1893 for the World’s Columbian Exposition as the World’s Congress Auxiliary Building, the Art Institute of Chicago remains one of the best museums in Chicago.

    • Lunch

      On Own

    • PM Activity

      The Amazing Race - Teambuilding In the highly customized, Amazing Race Chicago, your teams will compete to earn the most points by solving clues and reaching specific locations within the city which can include challenge stations and clues based on your company or mission.

    • Dinner

  • Day 2: Tours & Formal Dinner Reception

    • Breakfast

      Dine at Hotel

    • AM Activity

      Pedal the Lakefront Invite guests to enjoy the fresh air off the tourist beat and onto the quiet neighborhood streets, city parks, and packed beaches of the North Side of Chicago.

    • Lunch

      Meal Included in Activity

    • PM Activity

      Architectural River Cruise This river tour is widely considered the best 75-minutes a visitor can spend anywhere in the city. Guests will see more than 40 Chicago landmarks including Tribune Tower, Wrigley Building and Marina City.

    • Dinner

      GRAFF Chicago A private and exclusive event like no other, a dazzling cocktail hour while browsing and trying on fabulous diamonds followed a seated affair in Graff’s showroom atrium for a truly high-end dinner.

  • Day 3: Underground Speakeasy Life

    • Breakfast

      Dine at Hotel

    • AM Activity

      Frank Lloyd Wright Home & Studio Tour Guests will begin with a tour of Frank Lloyd Wright’s  home studio, which is the first place he experimented with design concepts that would influence his most well-known buildings. This will be followed by a historical neighborhood tour of Oak Park.

    • Lunch

      On Own

    • PM Activity

      Scandals & Speakeasies The tour is designed to unfold like a story, providing a prohibition themed, interactive guest experience. The experience is filled with rich chronicles of some of Chicago’s most infamous figures as well as some lesser known innovators that played a part in making the city what it is today.

    • Dinner

      Untitled Supper Club Offering a uniquely Chicago experience, Untitled Supper Club combines award-winning dining, sophisticated entertainment and dancing and the largest selection of American whiskey anywhere in the world.