Our Journeys

Long Weekend in Chicago with Chi O
October 27 - October 30, 2016

$1,995 USD

Long Weekend in Chicago with Chi O – Fall 2016

Ah Chicago . . . home of skyscrapers, deep-dish pizza, and the blues, and one of the most beautiful cosmopolitan cities in America. “Baby don’t you wanna go?”



DAY 1 - October 27 - Thursday - An introduction to Chicago

Upon arrival, guests will make their way to our hotel in Chicago’s exciting city center. Downtown Chicago has it all – amazing architecture, a beautiful waterfront, and quaint little neighborhoods lined with brownstones and flower boxes. We’ll first meet for drinks and dinner, and see if we can’t sneak in a little stroll to get a first taste of our playground for the weekend. Sleep in Chicago.

DAY 2 - October 28 - Friday - AIC and Millenium Park

Friday morning we will head toward Grant Park, “Chicago’s front yard,” to catch sight of the famous Buckingham Fountain, which is one of the biggest fountains in the world, and to visit the world-renowned Art Institute of Chicago. The Art Institute of Chicago is 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! Afterwards, relax in a nearby eatery on your own for lunch. Friday afternoon we will explore Millenium Park: A lively and spectacular gathering spot located in the heart of Chicago. Don’t miss the Crown Fountain and “The Bean”! We will enjoy some free time before heading to a very special group dinner. Sleep in Chicago.

DAY 3 - October 29 - Saturday - The Chicago River, shopping and the theatre

Saturday morning we will beat the crowd at the Willis Tower (a.k.a. Sears Tower) to see the city from above. We’ll have a chance to step out onto “the ledge,” which extends out from the Skydeck and offers the optimal experience of the second highest building in America.

Next we’ll 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.

It’s time. You knew it was coming. We must have deep-dish pizza. We will head to the well known Giordano’s Pizzeria and then “walk it off” on The Magnificent Mile, where we’ll 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. Saturday night we will venture to a nearby blues club to experience the music that made Chicago famous. Sleep in Chicago

DAY 4 - October 30 - 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 taken 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