South Side Essentials Tour

"Chicago - it's not just Navy Pier" Tour

South Side Essentials Tour begins at 1:00 pm sharp on select dates from Rock N Roll McDonald's - 600 North Clark Street - east entrance. After a brief introduction, guests embark on this one-of-a-kind exclusive bus tour in a comfortable air-controlled bus to explore the wonders of Chicago's South Side. During this excursion, guests will learn about and visit some of Chicago's most diverse and historical communities including some of the following; birthplace of Gospel Music, Sunset Café, President Obama’s home, site of 1893 World’s Fair, University of Chicago and home to the first sustained nuclear reaction, Union Stockyards, Bronzeville, Kenwood, Hyde Park, Bridgeport, Greektown, Chinatown, Little Italy, Ground Zero – Great Chicago Fire, Hull House and so much more!

Join us on this highly entertaining bus tour exploring the neighborhoods of Chicago. The South Side was and still is home to a countless number of important historical and famous residents. On this tour, we will trace the footsteps of some of these following figures; Barack Obama, Richard Wright, Ida B. Wells, The Marx Brothers, "Nat" King Cole, Louis Armstrong, Enrico Fermi, Daniel Burnham, Clarence Darrow, "Muddy" Waters, George Pullman, Julius Rosenwald, Stephen Douglas, Mahalia Jackson and so many more.

On this tour, we plan to dispel the misconceptions that Mrs. O'Leary's cow started the Great Fire and that the South Side is simply riddled with crumbling neighborhoods, crime and the disadvantaged. To the contrary, the South Side remains a flourishing collection of wonderful communities overflowing with warmth and intrigue. It is brimming with history and a wonderful collection of vibrant historical personalities!

On this exclusive tour, guests will view the city's breathtaking skyline from the best vantage point on land. They will hear stories about the 1893 World's Fair, "Black Metropolis", Chicago's Motor Row, Crime of the Century, Prairie Avenue - home of the rich and famous, Chess Records and so many more.

Tours includes snacks, beverages and fun trivia challenge with prizes. Restroom break is included halfway.

South Side Essentials Tour Highlights

  • Tour Duration: 3 hours
  • Tours begin and end at Rock N Roll McDonald’s - 600 North Clark Street - east entrance.
  • Tours are conducted in comfortable air conditioned/heated coaches - no double-deck buses.
  • Sunday afternoon tours only.
  • Tours begin at 1:00 pm sharp. Check-in begins at 12:30 pm. Restroom break half way through tour.
  • Guests will discover some of the following sites: birthplace of Gospel Music, Sunset Café, President Obama’s home, site of 1893 World’s Fair & University of Chicago,
  • Plus, the Union Stockyards, Prairie Avenue, Bronzeville, Kenwood, Hyde Park, Bridgeport, Greektown, U.S. Cellular Field, Chinatown, Little Italy, Ground Zero – Great Chicago Fire, Hull House and so much more!
  • Guests will hear some of the following stories; Burnham’s Plan - Beaches Lakefront & Marinas, World’s Fair of 1893, Union Stockyards, Blues, Jazz and Gospel Music and the Great Fire of 1871.
  • Reservations made by April 15 are only $30 and for those guests purchasing two different tours, the price drops to $25 per tour = 2 for 1 special.
  • Trivia challenge with prizes

Experience "true" Chicago on the South Side Essentials Tour!

Chicago's "South Side" has been fabled in both literature and song. It is home to some spectacular neighborhoods filled with an amazing history and numerous colorful characters. Ray Price said it best when he sang the following ditty:

"New Orleans was groovy Memphis light and gay
And who could put down New York's Broadway
But there was everything on the south side of Chicago
I still can hear those...
Yes there was everything on the south side of Chicago"



“Chicago finest tours-Southside tour”

5 of 5 stars

"Reviewed October 12, 2015

This was a great tour! Second one I have taken with them. First was the World's Fair tour. If you are lucky enough to have Dan as your tour guide you will be in for a great time his knowledge of, and passion, for Chicago is amazing! His sense of humor is great. These tours are very well organized and extremely interesting. If you are going to take a tour in Chicago you must try this company. You won't be disappointed. I am looking forward to going on another tour with this company!"

Visited October 2015


“South Side Tour - Amazing!”

Reviewed September 8, 2015 - 5 out of 5 Stars

"My boyfriend and I go on a lot of these tours - from a lot of different tour companies and we both agreed out of all of the tours we've been on (walking, riding, kayakig etc...) Dan ROCKED it! He was passionate, super informative and his love for Chicago clearly shines through in his work. He also made the tour super comfortable by providing water, pop and even beer as well as bags of popcorn for everyone and chocolates - at no charge! It was the only tour we've ever been on that gave out gift cards for correctly answering questions Dan asked throughout the tour which made it super interactive. Being born and raised in Chicago, we do know a lot of history and a lot of tours we do every year, give the same info. Not Dan's tour - SO much new information and extremely interesting! Two thumbs WAY up for Dan and Chicago's Finest Tours!!!! We will absolutely be riding/walking again with this company!"

Sharon R.

Chicago, IL


“The Essentials Tour South”

5 of 5 starsReviewed July 13, 2015 - 5 out of 5 Stars

"This tour was informative and entertaining. Our tour guide Dan was very knowledgeable and kept everyone on the tour interested. Tour had fun facts as well as historical insights into Chicago's South side. We enjoyed it and are looking forward to our next tour with Chicago Finest Tours."

John G.

Chicago, IL


“Great Tour of Southside Chicago”

Reviewed April 25, 2015 - 5 out of 5 Stars

"I am a lifetime resident of the Southside of Chicago, however when I went on a tour with Chicago Finest Tour I experienced the Southside of Chicago like I had never experience it before. The tour guide Dan was so knowledgeable and entertaining that I plan to take his other tours of the city. Just Great!!!"

Chuck R

Chicago, IL