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Best of Chicago - The Grand Tour

This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! See all the landmarks, attractions and historical sites of Chicago’s North Side and South Side and enjoy a scenic drive along the Outer Drive.

Get ready to see a wide array of landmarks, museums and historical sites on this comprehensive tour of Chicago which visits the city's north and side sides and their various highlights.

Using a luxury motorcoach to get around, you will also have an expert local guide who will provide plenty of insight and background information along the way.

North Side highlights of the tour include:

  • Central Business District one of the worlds financial hubs and always bustling with activity
  • The Loop the historical centre of downtown Chicago
  • State Street designated the great street by none other than Frank Sinatra
  • Richard J. Daley Plaza home to an untitled 15ft steel sculpture by Pablo Picasso
  • Wacker Drive a multi-level street winding its way through the city that has appeared in Hollywood films such as The Blues Brothers, Batman Begins & Batman The Dark Knight
  • The Chicago River its direction of flow reversed by a 19th century civil engineering master feat
  • The Magnificent Mile home to fine restaurants, nightlife, excellent shopping and several of the tallest buildings in the world
  • Lincoln Park fronting onto Lake Michigan this is Chicagos largest public park
  • Wrigley Field home to the Chicago cubs baseball team (wont be visited on game days)

South Side highlights of the tour include:

  • Grant Park referred to as Chicagos front yard and scene of President elect Barrack Obamas victory speech on 4th November 2008
  • Soldier Field home to the Chicago Bears NFL team
  • Adler Planetarium & Astronomy Museum the oldest planetarium in existence today
  • Shedd Aquarium the most popular cultural attraction in Chicago and at one time was the worlds largest aquarium
  • Field Museum of Natural History famous for the scope and size of its collection, and home to the most complete and best-preserved
  • Tyrannosaurus Rex fossil discovered yet
  • Art Institute of Chicago one of the USAs premier fine art galleries, renowned for its collections of Impressionist and American art
  • Jackson Park hosted the historic World's Fair Columbian exhibition in 1893
  • Lake Point Towers architecturally stunning and also the worlds tallest apartment building
  • Orchestra Hall home to the Chicago Symphony Orchestra
  • Navy Pier 1km long pier on the shores of Lake Michigan

Please bear in mind that you will not get off the coach and enter all of the places listed below however the tour will help you decide which ones to explore more thoroughly and show you where they are located.

Experience Includes

  • Comprehensive 4-hour guided tour of Chicago
  • Discover highlights of the South Side and North Side – a perfect overview of the Windy City!
  • Enjoy a scenic drive along the Outer Drive
  • Visit Lincoln Park, the Adler Planetarium, Wrigley Field and more
  • Transport by air-conditioned coach

Experience Excludes

  • Optional gratuities
  • Entrance to any of the museums or attractions
  • Pick-up and drop-off from downtown hotels in Chicago


Daily, year round.

Departure location

Grayline Office - details on voucher

Start times

10.00am and 12.00pm October to May; 9.30am, 11.30am or 1.30pm June to September.


Around 4 hours.

Terms & Conditions

  • The precise itinerary is subject to change depending on local conditions and unforeseen events.
  • The tour starts and ends at the at the Grayline Chicago office on Michigan Avenue. Directions will be on your voucher