The Best Tours in Chicago

There are over a hundred different tours in the city of Chicago. For the tourist that’s looking for the best of the best, we’ve compiled a list that we believe to be the top 5 tours in Chicago. We based this list off of personal experience, guest experience, and research from other review sites. We included schedules for the tours as well as where to buy tickets. Don’t forget about our Chicago city pass that saves you money on the top Chicago tourist activities HERE.

  1. Chicago Architecture River Boat Tour – While there are a few tours that concentrate on the architecture of Chicago, the most popular tour is called the First Lady Official Chicago Architectural Foundation River Tour (mouthful right?). This tour takes place on the Chicago river. Guests on this tour will cruise down the Chicago river admiring some of the most astounding architectural feats in the world and be told how and why it’s so awesome from someone who knows their stuff. Tour attendees will also learn the history of how Chicago developed some of the most innovative and beautiful buildings in the world. You’ll be able to hold a casual dinner conversation for so much longer after this tour.


  1. Segway tour – These types of tours have grown in popularity since segways have become more available to the general public. The most popular and best rated segway tour (according to TripAdvisor and our staff) is called Absolutely Chicago Segway Tour. Ride around like Paul Blart and see all the sites Downtown Chicago has to offer on a segway. Similar to the Architectural tour, guests will learn all about Chicago’s unique history and fun facts. This tour covers the most ground while still being able to be part of the actual city experience as opposed to being in a boat or trolley. Also, segways in general are just a lot of fun to ride around on.
  1. Untouchables Tour – During the prohibition era Chicago was a very different city from today. Mafia, corruption, and crime ruled the streets. The Untouchables tour let’s guests see all the  old Mob hangouts, hideouts, and shootings that occurred in the 1920’s gangland of Chicago. See where infamous mafia leaders like Al Capone liked to have a drink and where the St. Valentines Massacre took place. For those that love the darker side of American history, this tour is a must go.
  1. Tastebud tours – Food tours are a dime a dozen in Chicago. After all Chicago has become a top contender in the culinary world. Tastebud Tours gives the best overall taste that is Chicago food. Sample more than just Chicago style pizza and hot dogs, and really learn about how Chicago’s melting pot culture shaped Chicago cuisine. Sample foods in the Chicago Loop including Millennium Park,  the beautiful Gold Coast neighborhood and the Magnificent Mile. Not only do we think this is the best food tour in Chicago but it was voted number #1 food tour by the Chicago Traveler.
  1. Urban Kayaks – For the more active visitor, the Urban Kayak is similar to the Chicago Architecture tour, but you’re in charge of the boat, or kayak in this case. Cruise down the Chicago rive in a kayak. We really recommend not getting any of the water in your mouth, but other than that the Urban Kayak tour is an exciting way to see downtown Chicago and get a little workout at the same time.

If you are interested in learning more about all the tours that take place in Chicago, Visit Here