Stories of Chicago

  • 4 Days
  • 5 meals
  • City Discoveries
  • Culture
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Program Overview

Experience the glitter and grit of the Windy City of Chicago, discovering gangster stories, historic architecture and tasting the authentic deep-dish pizza. Explore the sights and sounds of the city from Michigan Avenue to the Navy Pier. Stroll through Millenium Park to see the curated architecture, landscaping and local art, including the famous Cloud Gate sculpture, aka The Bean. Go on a narrative cruise on the Chicago River to discover the bold architecture that is a defining characteristic of the city. Uncover the secrets of Chicago’s streets on a tour with a guide dressed in a 1920s gangster costume, listening to the exploits of Capone, Morgan and Dillinger. Stop by significant sites of crime stories, including the St. Valentine’s Day Massacre, the Biograph Theatre and Holy Name Cathedral.

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Daily Itinerary

Day 1

Travel to Chicago

Welcome to the Windy City

Travel to the Windy City of Chicago in Illinois and meet the Tour Director who provides ongoing guidance for the duration of the trip. Take an introductory sightseeing tour covering Michigan Avenue, the Magnificent Mile, the Loop, Lakeshore Drive and Navy Pier. Go on a walking tour of Millenium Park and stop by The Bean sculpture for a photo opportunity. Settle in to nearby accommodations in time for a welcome dinner.

  • Introductory TD tour of Chicago
  • Walking tour of Millenium Park and The Bean photo op
  • Welcome dinner
  • Dinner

Day 2


Journey of Discovery

Hear the fascinating stories of local architecture and history on a relaxing Chicago River cruise. During this comprehensive tour, see more than 40 landmark buildings that make the city such an incredible destination. Discover more during free time this afternoon, circling back to locations from the cruise or finding a new place to visit, such as the Art Institute, Field Museum and Shedd Aquarium.

  • Architectural river cruise
  • Free time to explore
  • Breakfast

Day 3


Secrets of History

Step back in time to the Prohibition era, listening to a costumed guide on a tour through the streets of Chicago to uncover the exploits of famous gangsters. Find hidden gems that only locals know about on the Wicker Park Culture & Chicago Street Art Tour, exploring the art galleries, architecture and history in this popular neighborhood. Experience the deep-dish pizza Chicago is known for during the farewell dinner. Afterwards, attend an improv show.

  • Gangster tour
  • Wicker Park Culture & Chicago Street Art Tour
  • Deep-dish pizza farewell dinner and improv show
  • Breakfast
  • Dinner

Day 4

Chicago to Home

Travel Day

Enjoy free time to explore before departing Chicago and beginning the journey home.

  • Breakfast

Services Included


Quality, safe hotels with twin occupancy corresponding to the destination.


Daily breakfast with a mix of lunches and dinners, as stated in the itinerary.

Ground Transportation

All transportation is provided for activities included in the trip itinerary.

Curated Experiences

Curated experiences developed by travel experts.

Tours and Activities

Scheduled activities, experiences and guided tours are all included as listed in the itinerary.

Audio Headsets

Audio headsets for flexible sightseeing.

Full-Time Tour Directors

Full-time Tour Directors are on site for the duration of the trip.


Tips for bus drivers, guides, Tour Directors and meals.

24/7 Support

Dedicated 24/7 staff availability, supporting travelers every step of the way.

Interactive Technology

Advanced travel software that integrates geofencing, logistics, communication and more optimized safety features.

Not Included

Porterage services, housekeeping, airport transfers on the first and last day of the trip if not traveling with a group (unless previously arranged).

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Advanced Student Security Software

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