Chicago Highlights Tour & Architectural Boat Cruise 2020 New Dates


Available Tours

  • Oct 05 - Oct 08, 2020 - chicago Highlights - (Available)

Chicago Highlights Tour 2020

Featuring Architectural Boat Cruise, Gangster Dinner Show & More! Sold out in 2019!

4 Days – 3 Nights
May 26th -29th  ——   Cancelled Covid-19
August 24th– 27 Cancelled Covid 19                                              
October 5th – 8th
 Our Chicago Highlights tour includes amazing guides, attractions and delicious breakfasts and dinners at local restaurants. Make sure when you check out other competitors you find out what’s included in the price! That has always been the difference with our Tours.  Known as “The Windy City”, Chicago is one of the largest cities in the U.S. Famed for its bold architecture and skyline punctuated by skyscrapers.  A local step on guide will show us all the highlights of Chicago and a boat cruise will give you all the history of their famous waterfront.  An evening visit to Gangster “Tommy Gun’s Garage” for dinner and show will be a highlight for everyone.  Each night you will enjoy the great lineup of restaurants we have carefully selected.  You will also enjoy a ride to the top of a monster skyscraper for the best view of Chicago (if you’re brave enough). Rounding out this great trip is a shopping excursion at the Magnificent Mile and free time to explore on your own. This tour has it all and is one of our favorites!



  • 3 nights’ accommodation at the Holiday Inn Express—Crestwood, IL
  • All breakfasts and Dinners included!
  • Deluxe Continental Breakfast at hotel each morning,
  • 2 Dinners included at local Restaurants ex. Buca di Beppo
  • Dinner Theatre show in Chicago at Tommy Gun’s Garage
  • Guided tour of famous Chicago City
  • Visits to local Chicago attractions including Navy Pier, Millennium Park and Wrigley’s Field
  • Admission to one of Chicago’s skyscraper observatories for magnificent views
  • Architectural Boat cruise
  • Shopping at Magnificent mile
  • Duty Free stop
  • All taxes and baggage handling included
  • Deluxe Motorcoach Transportation
  • Fully Escorted by Front Line Tours! Games and movies on coach!

Cost Per Person:                                                       

  Twin:         $779.00     

  Single:       $929.00    

 Triple/Quad:  $729.00    

*Deposit of $200 required upon booking

Balance of payment due

30 days prior to tour departure*


Pay a deposit of $200 per item

Traveler 1

Traveler 2

Traveler 3

SKU: N/A Category: Tag:

Additional information

Available Tours

May 26 2020 – May 29 2020, Aug 24 2020 – Aug 27 2020, Oct 5-8 2020

Insurance Quote



, ,