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Chicago Walking Tours


See our Calendar Below for All Tours, as well as Things to Do & Travel Tips

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Architecture Tour

Our Chicago Architecture Tour will lead you along the Riverwalk through the history of the industrial landscape that is home to the world’s first skyscraper
Schedule: 1-2 A Week
Start Time: 10am
Tour Language: English
Duration: 2 Hours
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Architecture Tour Highlights

  • Willis/Sears Tower
  • CME Center (the exchange)
  • Civic Opera Building
  • N. Riverside Plaza
  • 33 West Wacker
  • Merchandise Mart
  • Trump Tower
  • Leo Burnett Building
  • NBC Tower
  • Marina City
  • 35 East Wacker Drive
  • Tribune Tower
  • Crain Communications Center
  • Cloudgate (actual title of “the bean”)
  • Crown Fountain
  • 1 W Washington (Atwood Café/Hotel Burnham)

Haunted History

Walk with us as the sun sets through downtown Chicago hearing some of the most gruesome and creepy Chicago stories. Expect more history and humor than hauntings. Our guides aim to tell you the history of the darker side of Chicago with stories of eerie coincidences and stories from the past. We don't promise any hauntings as we haven't seen any ghosts ... yet
Schedule: 3-4 Times a Week
Start Time: 6pm
Tour Language: English
Duration: 2 Hours
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Haunted History Highlights

  • The Congress Hotel
  • Chicago’s old Red Light District
  • Murderous Tales of H. H. Holmes and John Wayne Gacy
  • Chicago Fire Hangman
  • Death Alley and the Iroquois Theatre Fire
  • S.S. Eastland Disaster Hauntings

Loop and Millennium Park

Join us on the Free Chicago Loop Tour of Downtown Chicago. Learn about history, architecture and other hidden treasures. Tours run on a pay-what-you-want basis.
Schedule: 1-2 a Week
Start Time: 10am
Tour Language: English
Duration: 2 Hours
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Loop and Millennium Park Highlights

Chicago Pedway Tour

On the Chicago Pedway tour, we will navigate and explore the Chicago's series of mostly indoor tunnels, bridges, and paths throughout the downtown Loop.

Riverwalk and History Tour

You will learn about Chicago's greatest triumphs as well as her most devastating tragedies.  You will see the birthplace of the city where the original army settlements were.  Since this tour is on foot, you will get to pause and really appreciate each architectural gem.
Schedule: 2-3 A Week
Start Time: 2pm & 6pm
Tour Language: English
Duration: 2 Hours
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Riverwalk and History Tour Highlights

  • The Chicago River
  • Original settlement of Fort Dearborn
  • The Jeweler’s Building
  • The Aqua Building
  • The Wrigley Building
  • The Marina City Towers
  • History of the Chicago Flag
  • and much more!

Lincoln Park & Blues

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. 
Schedule: 3-4 Week
Start Time: 2pm
Tour Language: English
Duration: 2 Hours
View Highlights

Lincoln Park & Blues Highlights

  • History of Blues and Chicago Gangsters
  • DePaul University
  • Biograph Theatre where Dillinger was killed
  • Red Lion Pub
  • Oz Park
  • Architectural gems by Bruce Graham and Louis Sullivan
  • Site of St. Valentine's Day Massacre

Free Tours by Foot is pleased to present the best pay-what-you-like guided Chicago walking tours. 

These interesting and informative sightseeing city tours will take you through many of the Windy City's most famous neighborhoods.

Everyone should be permitted to take a guided tour for a price they feel it was worth or what they could afford – even free!  

Pay-what-you-like tours are tours for every budget.  


We provide a platform for local, freelance tour guides to lead walking tours as well as ghost and architecture tours at no upfront cost, so that you may enjoy a worry-free quality sightseeing experience.

Walking tours are our forte, and we offer a number of daily and weekly pay-what-you-like walking tours of Chicago as well as completely free self-guided options.

You could browse the tours that we have by clicking the links below, by scrolling our public calendar (also below) or it just might be best to go directly to our booking page

There’s no cost to book our walking tours. 

We have roughly 1000 reviews with a rating of 5 out of 5 stars and with 97% of reviewers rating us as very good or excellent.

We are so well-reviewed, yet TripAdvisor seems to hide us from you (probably because they can’t sell our tours for commission).  Read the reviews for yourself.  

Our premiere Chicago walking tours are great day or night and serve as introductions to the city, Chicago history and cover the many of the main tourist attractions. 

Our Regularly Scheduled Tours

  • The Birth of the Skyscraper: Architecture Tour is a great way to discover and appreciate the incredible landscape of buildings in Chicago and it ends in Grant Park near the famed Buckingham Fountain.
  • The Riverwalk and Chicago History Tour follows the path of the Chicago River and focuses on the history of Chicago, the Chicago Flag, and the beautiful buildings that line the river.
  • North Loop and Millennium Park Tour, which covers a great portion of Chicago’s downtown Loop neighborhood, public art, and ends in Millennium Park.
  • Our Chicago Ghost Tour -Haunting History is for folks who love haunting history and creepy tales of the dark side of the White City.
  • On The Magnificent Mile Tour, you will discover fun Chicago facts like the history of deep dish pizza while exploring our most popular downtown area.

Weekly Tours

  • Our Gold Coast Tour meanders through the history of high society where you will be introduced to the glamorous residential neighborhood built around Lakeshore Drive.
  • Explore Lincoln Park on our Lincoln Park and Gangster Tour to appreciate a unique neighborhood scattered with hidden history including tales of Chicago Gangsters.
  • We also offer a West Loop tour which combines great storytelling for history buffs with great photo ops for those more in the “sightseeing” mood! 
  • Get out of downtown and check out the Chicago Street Art on our Wicker Park Culture & Street Art tour.

Winter Tours

We offer tours year-round, even in Chicago's winter, but we take into account the need to be seasonably appropriate for walking tours. Check out our special Winter offers:

  • In the winter, we offer a Pedway Tour that explores the indoor tunnels and paths to discover Chicago architecture and arts in a warmer way.
  • There is also a Winter Loop option where we will spend about half of the time outdoors looking up at the skyscrapers and the other half will be spent inside exquisite public buildings and lobbies.
  • Our Winter Architecture Tour explores the unique landscape of buildings in the downtown area while also popping into many lovely lobbies for warmth!  This tour is abbreviated and adjusted for our Chicago winters.

En Español:


Many of our pay-what-you-like walking tours are architecture tours or architectural points are a large part of them.

These tours include:

In addition to our walking tours, there are other walking tour companies that offer excellent architecture tours.

Another popular option is to take an architectural boat cruise. There are even architectural tours by bus as well as Segway.

If you are on a budget or would just like to take things at your own pace, then consider one of our self-guided walks.


In addition to walking tours, Chicago has bus, bike & boat tours. Read all about them...


We also offer our guiding services for private groups, families, or school groups where we can guide you in the Loop, the South Side and anywhere else in Chicago.

Find out more about private tours...

And much, much more

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