Tour Calendar | Chicago Walking Tours

We offer a lot of tours – not sure which one is best for you? Check out the quick summary of our tours below the calendar.

  • If you have a group or want a tour at a time to suit you, we offer private tour as well.
  • Check out our self guided tours of Chicago so you can explore the city on your own.

Due to city regulations and the overall enjoyment of guests, we limit our tour size. Our tours are very popular and we often are forced to turn away many interested guests. We have found that groups have a higher than average no show rate. In order to be fair to everyone, we generally do not allow groups of 6 or more on our public tours without prepayment, which can be done on our Booking Page.

Tour Summaries

Loop & Millennium Park Tour: Join Free Tours by Foot on this fun and engaging walk through the Chicago’s North Loop.  Come and learn about how the Great Fire of 1871 started and marvel at the modern city that rose upon the ashes of the old city.  See North Loop gems like the iconic Chicago Theatre marquee or the Louis C. Tiffany mosaic that is hidden in plain sight!  Take a selfie at the start of the legendary Route 66 and discover the extravagant interior of the Palmer House.  This tour ends in Millennium Park, Chicago’s still new and much loved public park.

Chicago Architecture Tour: Join your guide for a fun and interesting walk filled with stories about Chicago.  Discover the oldest operating el train station in Chicago and gaze upon the building that held the record for the World’s tallest from 1973-1993.  Take in the scenery of our man-made “canyon” of La Salle Street and get a taste for Frank Lloyd Wright’s artistry. The tour ends in Grant Park a few steps from Lake Michigan at the magnificent rococo-style Buckingham Fountain.

Magnificent Mile Tour: Join our guide for a stroll down the Mag Mile discovering many things you might not have noticed while grabbing your latte or browsing in Forever 21.  For example, did you know that along Michigan Ave you will find the very first health club for women?  Or that the historic Palmolive building was once called the Playboy building while it housed Playboy, inc? You will see architectural masterpieces from the Tribune Tower to the John Hancock Building.  This stretch of street even boasts the oldest building in Chicago!  Your guide will talk about Chicago favorites including the original deep dish pizza and some of our famous residents!

Chicago Ghost Tour: The Windy City is known for her food, architecture, and haunting history! Walk with us as the sun sets through downtown Chicago hearing some of the most gruesome and creepy Chicago stories. First stop is the Congress Hotel, known as the most haunted hotel in Chicago. Walk along the streets that H. H. Holmes, Chicago’s first serial killer wandered as he stalked his prey, get a glimpse of Chicago’s sordid past through stories of the Everleigh Club and the 1900’s Red Light district, and learn about downtown prison breaks.

Lincoln Park & Gangster Tour: Join Free Tours by Foot as we venture through one of Chicago’s well known neighborhoods, Lincoln Park.  Famous for hidden gems, hired guns, and hot guitars, our guide will lead you through the neighborhood to view the unique and residential streets.  You’ll walk the footsteps of Chicago’s notorious gangsters and learn about how prohibition effected Chicago.  We’ll walk through Lincoln Avenue Bar District and hope to hear the strains of blues guitars from the pubs and music venues. The tour ends at Lincoln Park, the park which the neighborhood is named after.  You will be steps away from visiting the Lincoln Park Conservatory or the Lincoln Park Zoo.

Giants in the Park: Statues, Stories & History of Lincoln Park: Lincoln Park, historically Chicago’s great place of leisure, is also an outdoor art and history museum.  Take a sculpture tour of this north-side playground and encounter GIANTS of history and literature, celebrated in enduring bronze. While learning the histories behind local monumental art, we will glimpse moments and ideals from this great city’s youth. The tour concludes in the gardens outside the Lincoln Park Zoo, the Lincoln Park Conservatory and nearby popular Lincoln Park restaurants.

Riverwalk & History Tour: Join Free Tours by Foot as we take a leisurely stroll along the northern reaches of the Chicago River and take in the beautiful architecture, such as the Tribune Building, and learn the stories behind the men and woman who built them. The tour ending point is near Municipal Pier #2 (better known as Navy Pier), where you can easily stroll over to see the sites- including the Ferris wheel and the Stained Glass Museum. The Pier is filled with delicious Chicago favorites like Garrett’s Popcorn, Chicago style hotdogs (NO ketchup allowed), and of course, a Billy Goat Tavern.

Chicago Pedway Tour: On the Chicago Pedway tour, we will be indoors for most of the tour navigating and exploring the Chicago Pedway System. The Pedway is a series of mostly indoor tunnels, bridges, and paths throughout downtown Chicago. While on this tour, we will see Chicago’s famous architecture while peering out of the windows of intricate lobbies, amazing examples of art, and we’ll discover some of the best “secret-eats” in the city- all while enjoying the comfort of the temperature regulated pathways! This tour is offered in Winter Only.

Chicago Holiday Tour: Welcome to Chicago: a city that loves to deck the halls while watching “Home Alone” in our Rudolph p.j.s. Join our guides for a stroll in downtown Chicago visiting some of our favorite holiday spots! You will visit the traditional Chicago Christmas tree, scope out good places for ice skating, and discover a few places to grab an indulgent dessert. The guide will show you one of the oldest continuously operating hotels in the city which will certainly be festive! The tour will end of the German Christkindlmarket in Daley Plaza where guests can enjoy the festival that will have food, spiced wine, cocoa, and plenty of cheer. This tour is offered in Winter Only.