South Side Tour by Gray Line

5/5 (1 Reviews)
Take in highlights of the South Shore — from Grant Park ("the front lawn of the city") to the eclectic neighborhoods, the University of Chicago and more. Bonus: After the two hour tour, you'll have plenty of time to take a closer look at your favorite sights.
  • Adult gate price $28.00
  • Child gate price $14.00
  • Add to pass

Historic, cultural Chicago is on full display during this fantastic two-hour Gray Line South Shore Tour. Travel through Grant Park, the front lawn of the city and site of Soldier Field, where you might hear music from the Joseph Petrillo outdoor band-shell on a warm summer night!

Why would you rent a car and struggle with parking in a city? Sure you can take public transportation, and zoom by (or under) the beautiful attractions and buildings. But will you really have any idea what they are and how they came to be? Not unless you spend hours researching before your trip, plan a strict itinerary, and carefully plot each stop using a map that quite frankly, is so difficult to re-fold that it makes you want to hide under the bed in your hotel room and cry. Skip the nightmares of self-planned vacations, and let Gray Line do the legwork for you. Just sit back and enjoy Chicago! What will you see on your trip?

Gray Line Chicago brings you a very comprehensive tour of Chicago’s South Shore that lets you in on the history and secrets of “The City by the Lake”, visiting parks, university campuses, music halls, museums, the lake (naturally), and of course—more of those stunning and super-unique buildings that make Chicago the architectural heart of the Western world!

This South Shore Tour will take you past:

  • The Art Institute of Chicago, renowned for its vast collection of impressionist art
  • Orchestra Hall, home of the famous Chicago Symphony Orchestra
  • The Field Museum of Natural History
  • The totally unique 80-floor Amoco Oil Building, which is completely faced in white granite.
  • “South Commons”, a one-of-a-kind closed-in residential community.
  • The green oasis of Jackson Park, where the Colombian Exposition of 1893 was held in celebration of the founding of America 400 years earlier!
  • The University of Chicago, a campus renowned for its elegant English-style architecture.
  • Lake Point Towers—once the world’s tallest apartment building—a stunning design feat of glass and curves.
  • This trip brings you the highlights of the South Shore in just two hours, leaving you with plenty of free time to explore the individual sights on foot…now that you have a good overview on what you want see!

    Gray Line Chicago’s South Shore Tour will stop for a photography break, letting you capture the beauty of the Museum Campus (or will substitute a stop elsewhere depending on time constraints). One really cool perk of this trip is that Gray Line Chicago, as a way of thanking customers for their patronage, operates a free shuttle service from 69 Chicago-area hotels to the South Shore Tour’s departure point. Enjoy the ride!

Reviews for South Side Tour by Gray Line

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[3 of 5 customers found this review helpful]

Great few hours - very worth while
By Lawrence Verified Reviewer from Manchester England on
Bottom Line:
Yes, I would recommend this to a friend

Comments about Smart Destinations South Side Tour by Gray Line:

Although we had visited a lot on the South side of Chicago ( Alder building etc) it was good that the tour took us into the suburbs to see sites that you would not see without having the tour.

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Phone: 312-251-3100


17 E. Monroe Street
Palmer House Hilton arcade office
Chicago, IL 60603


June-September: Tour departs at 11:30 am and 3:30 pm
October–May: Tour departs at 12:00 pm.


Look for Gray Line tour guides who are easily identified by their blue shirts. Tours are occasionally not operational due to special events, outside of the control of Smart Destinations.


New Year’s Day
Thanksgiving Day
Christmas Day
All holiday hours are subject to change without notice.
  • Open year-round
  • Good for families
  • No parking available
  • No restaurant or snack bar
  • No restrooms
  • No disabled access
  • Reservations not required


17 E. Monroe Street
Palmer House Hilton arcade office
Chicago, IL 60603

Public Transportation

Take CTA: Blue Line to Monroe and Dearborn Street

Please present your Go Select Pass at the Grayline ticket office window in the Palmer House Hilton (17 E. Monroe). It will be validated, and returned with a ticket for the South Side Tour.

This tour departs from the Gray Line office located at the Palmer House Hilton Hotel. Please arrive a minimum of 1/2 hour prior to the scheduled departure time. Tour is based on availability on the day of service. Tours are occasionally not operational due to special events, outside of our control.

Note: Look for Gray Line tour guides who are easily identified by their blue shirts.

Save even more with these pre-built discount packages that include South Side Tour by Gray Line bundled with other great Chicago attractions.

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