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Things To Do in Chicago

Chicago Trolley Tours

1709 South Prairie Ave (office), Chicago, Illinois 60658

Featured Review : I usually make it a practice to take some sort of a trolley tour when I visit a city for the first time. After dropping our bags at Flemish House, we walked up to North Michigan Avenue and headed south. I had no specific...See Full Review

  • #5 most popular
    thing to do in Chicago
  • Avg. User Rating:
    4 out of 5 stars

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Chicago Trolley Tours Reviews

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LOVED IT!

  • 5 out of 5 stars by villageofwolf from Fulton County, Ohio
  • May 20, 2025
Quote: It was our first time Chicago and I can't even think of a better way to see the city and stop at all the great sites. Not only did the bus tour hit all the great spots so we could hop off and check them out BUT the tour guides where awesome. Every... Read the full Chicago Trolley Tours review

Best of Chi!

  • 5 out of 5 stars by 1035 Kiss Fm from Chicago, Illinois
  • April 26, 2025
Quote: Hop-on Hop-off Trolley tours just won for best city tour in Chicago! Check out what else won for best of Chi-Town with 1035 Kiss Fm!http://www.kiss1035.com/pages/bestchiresults2010.html

A Tourist in My City! Fantastic!!!

  • 5 out of 5 stars by mmurphy55 from chicago, Illinois
  • February 18, 2025
Quote: I am a born and raised South-Chicagoian, and when my relatives from San Francisco CA, came to visit last week I wanted to make their first trip to the Windy City as fun and eventful as possible! We went to see Jersey Boys, had plenty of pizza, and... Read the full Chicago Trolley Tours review

Chicago Trolley Tours

  • 5 out of 5 stars by bingesf from chicago, Illinois
  • June 7, 2025
Quote: I had the best time on the Chicago Trolley and Double Decker tour! On top of a Double Decker is the only way to see the city. My elderly father had come to visit, and we were looking for convenient ways to sightsee around the city that would... Read the full Chicago Trolley Tours review

From journal Family Visit

Chicago Trolley Tour

  • 5 out of 5 stars by momo123 from Chicago, Illinois
  • June 4, 2025
Quote: I live here in Chicago and, this past weekend, my parents came to visit. Usually when they visit, I try to show them around myself and I spout off what facts I know or can make up about various landmarks around town. This time, we decided to... Read the full Chicago Trolley Tours review

From journal Chicago city tour

Chicago Trolley Tours

  • 5 out of 5 stars by favreforprez from Sturgeon Bay, Wisconsin
  • June 3, 2025
Quote: My friends and I decided to drive down to Chicago from our homes in Wisconsin for the Memorial Day Weekend. We got into town early Friday morning and decided that the best way to start out our weekend would be to take a tour of the city. We were... Read the full Chicago Trolley Tours review

From journal Touring Chicago

Best of IgoUgo

Chicago Trolley Company

  • 5 out of 5 stars by boilergumby from Elmhurst, Illinois
  • June 2, 2025
Quote: My wife and I have lived in Chicago’s western suburbs most of our lives. We thought we had seen the city from all of its most fantastic perspectives. We were wrong!One recent hot May morning, my wife and I decided to hop on the Metra train and... Read the full Chicago Trolley Tours review

From journal Fabulous Tour of Chicago

Chicago Trolley Company

  • 5 out of 5 stars by hckygrl12 from Chicago, Illinois
  • April 23, 2025
Quote: I have lived in Chicago my entire life and thought I knew all there was to know about the city. I was wrong! After graduating from college, my friends and I went to Chicago for a day of fun. We wanted to get around the city without having to walk... Read the full Chicago Trolley Tours review

From journal Chicago Trolley Fun

Chicago Trolley Tours

  • 5 out of 5 stars by NoFunNDaSun from melbourne, Florida
  • April 20, 2025
Quote: My wife and I are big travelers and have visited most medium and big cities in the U.S. Whenever we travel we always try and utilize a tour similar to this to learn about the city and to use as a way of hopping around the city. Of all... Read the full Chicago Trolley Tours review

From journal Chicago Weekend

Best of IgoUgo

Chicago Trolley Tours

  • 4 out of 5 stars by zabelle from Portland, Connecticut
  • October 31, 2025
Quote: I usually make it a practice to take some sort of a trolley tour when I visit a city for the first time. After dropping our bags at Flemish House, we walked up to North Michigan Avenue and headed south. I had no specific agenda in mind just trying... Read the full Chicago Trolley Tours review

From journal Getting Together in Chicago