The Highlights Of Chicago – 3 Days

Three days in Chicago, The Windy City, exploring the history and some of the seedier elements of prohibition, architecture & history


Program Summary

Spend three days in Chicago

Program Highlights & Inclusions

  • Free time at the Magnificent Mile
  • ETA Tour Manager throughout your trip
  • Transportation throughout your trip
  • Admission to the Art Institute of Chicago
  • Visit to Millennium Park
  • Experience “Chicago’s Original Gangster” Tour
  • Visit the Rock n Roll McDonald’s in Chicago
  • Admission to the Museum of Science and Industry
  • Admission to Chicago’s Skydeck
  • Free time at Navy Pier
  • Guided Architecture Cruise on the Chicago River
  • Admission to the Shedd Aquarium

Daily Itinerary

You’ll spend three days in Chicago, The Windy City, where you’ll explore the architecture, history and art.


Upon arrival in Chicago, you will meet your Tour Manager and enjoy free time exploring the Magnificent Mile.

Next, you will visit the Art Institute of Chicago. This Classical Renaissance structure, guarded by two bronze lions at its entrance, boasts one of the world’s great art collections, including the trademark “American Gothic.”

You’ll visit Millennium Park, where you’ll see the amazing art and architecture including the reflective Kapoor Sculpture at Cloud Gate, the BP Bridge, the Jay Pritzker Pavilion and more.

Tonight you’ll experience authentic Chicago-style deep-dish pizza before returning to the hotel for the evening.


This morning you’ll take a guided tour on your bus and experience Chicago as it was during the 1920s and 30s! See the old gangster hot spots and hit spots and hear historically accurate accounts of the exploits of Capone, Moran, Dillinger and the rest a da boys! Feel the excitement of jazz-age Chicago during the era of Prohibition! Enjoy a journey into the past as you cruise the city in search of the old hoodlum haunts, brothels, gambling dens and sites of gangland shootouts!

Next, you’ll visit the original McDonald’s Flagship restaurant in Chicago. The Rock ‘n’ Roll McDonald’s features a collection of memorabilia from the 1950s and ’60s, including Elvis Presley on the cover of Time magazine, a plaster cast of the Beatles and an authentic 1958 Corvette.

After lunch, you will enjoy live science experiences at the largest science museum in the Western Hemisphere at the Museum of Science and Industry.

You will then enjoy spectacular views spanning up to four states from atop the Chicago Skydeck.

This evening you will explore Navy Pier. Located on the shoreline of Lake Michigan, Navy Pier showcases a unique collection of restaurants and shops in addition to unequaled recreational and exhibition facilities – in a setting like no other!


This morning you will experience the beauty of Chicago on a sightseeing architecture river tour. This 60-minute tour takes you past dozens of world-renowned buildings, including Tribune Tower, the Wrigley Building, Marina City, and Willis (Sears) Tower. Your entertaining boat guides will enthrall you with the stories behind these, and dozens of other, Chicago landmarks.

After lunch, you will visit the Shedd Aquarium, the largest indoor aquarium in the world, with more than 8,000 aquatic animals.

Your Chicago journey comes to a close as you begin the return trip home.

Our Price Guarantee

We know how hidden costs can ruin a program. Our tours are fully inclusive; there are no hidden costs or surcharges. Once your group enrolls in a trip, the price will never change. Here is what you will get on every trip:


Every program is unique & tailored for your group.

Flexible Payments

A variety of online, scheduled & recurring payment options.

Affordability & Quality

Providing the best experience & best value for your dollar.

Chaperones Travel Free

Just tell us how many free places you need.

Insurance Plans

Medical, trip delay cancellation & optional “any reason” option.

Transportation Covered

We include all transportation to, from and during your trip.

Paid Entrance Fees

Fees and/or tickets are covered if included in your itinerary.

Paid Meals

You choose which meals are included in your program.