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Free Chicago Walking Tours will make sure that you see a new and exciting side of Chicago on our 2-hour FREE walking tour. Our interactive walking tour will surprise even the experts in Chicago trivia. Free Chicago Walking Tours guarantees you will meet people, have fun and learn. Reserve online today!

 
Free Chicago Walking Tours

Free Chicago Walking Tours offers 2 hour walking tours that cover the best Chicago neighborhoods and most popular Chicago tourist sights making sure that you can cross off plenty from your Chicago-to-do-list.

Free Chicago Walking Tours Available:

View the most up-to-date schedule and reserve your Free Chicago Walking Tour by using our Tour Calendar. We limit the size of our tours and require reservations.

If you have a large group we also offer Private Tours that can be customized to meet your groups needs.

Free Chicago Walking Tours will last for 2 hours with a distance no longer than 2 miles. We focus on three main things with our tours: Meeting People, Learning & Having Fun. Free Chicago Walking Tours is not your average walking tour. Read about The Experience and visit our FAQ page for more details.

Free Chicago Walking Tours are built by Our Local Chicago Guides who all share a passion for the city we call home. Each guide has carefully constructed their tours to ensure the perfect mix of their personalities, Chicago’s history & Chicago’s architecture. If you’re new to Chicago be sure to read our Chicago Blog for tips and tricks on how to make your stay more pleasant including Your Guide to Getting Around Chicago & Top 20 Free Things to do in Chicago.

Chicago Walking Tours: River & North Loop Walking Tour

Chicago Walking Tours Riverwalk Chicago Walking Tours Riverwalk Chicago Walking Tours Riverwalk

Guests will enjoy the perfect mix of Chicago history, architecture and beautiful views along the Chicago Riverwalk. This Chicago Walking tour has something for everyone.

This tour begins at the Du Sable Bridge – where it all began for Chicago back in the 1600s. The group will walk west along the river soaking in the beautiful architecture. Guests will hear the story about the Eastland disaster – one of America’s worse maritime tragedies ever.  Heading south into The Loop the group will stop by Daley Plaza and visit the Picasso in Chicago. Our tour ends at the Chicago Cultural Center. You will be impressed with the amount of sights and information we cover in just 2 hours!

Meeting Point: Southwest corner of the Michigan Ave. Bridge, known as the Du Sable Bridge. The exact spot could also be considered the Northwest corner of the Michigan and Wacker intersection. Google Maps

Start Time: We run this tour at 2pm on Saturdays. Check our calendar and Reserve Online today.

Distance: 1.7 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

    • Gorgeous Chicago River
    • Jewelers Building
    • Heard Square Monument
    • Trump Tower
    • Marina City Towers
    • State of Illinois Building
    • Daley Plaza
    • Picasso in Chicago
    • Chicago Cultural Center

Stories you will be told: 

      • The beginning of Chicago
      • Trump International Hotel & Tower
      • The Financiers of the American Revolutionary War
      • Why is it called the Jewelers Building
      • Eastland Disaster
      • Surprise! Guess what’s under the paint?
      • Chicago’s Most Unique Building (State of IL Building)
      • Picasso comes to Chicago

Chicago Walking Tours: Loop Architecture Tour

Chicago Walking Tours Loop Architecture Chicago Walking Tours Loop Architecture Chicago Walking Tours Loop Architecture

Chicago is very well known for it’s incredible architecture – and for good reason. Given a blank canvas after the Great Chicago Fire of 1871 and the newly discovered steel-frame building Chicago quickly became the skyscraper capital of the world.

Learn about the varied and brilliant architecture found throughout the Loop on your journey starting at the iconic Willis Tower (Sears Tower) and concluding in Millennium Park. Our guide will share the history of Chicago and explain the multiple architectural influences that helped shape Chicago’s incredible skyline.

Meeting Point: Outside the Willis Tower Skydeck Entrance (320 W. Jackson Blvd)

Start Time: We run this tour at 1pm on Wednesdays and Sundays. Check our calendar and Reserve Online today.

Distance: 1.7 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

      • Willis Tower
      • Rookery Building
      • Chicago Board of Trade
      • Federal Plaza
      • Marquette Building
      • Daley Plaza

    • Chicago Cultural Center
    • Millennium Park & Cloud Gate

Chicago Walking Tours: “Total” Loop Walking Tour

Chicago Walking Tours Total LoopChicago Walking Tours Total LoopChicago Walking Tours Total Loop

The Loop is where the American “downtown” was born. Home to international business headquarters, high finance, and arms of the federal, state, and local government, the canyons of skyscrapers within the boundary of the “El” system are the definition of “The City”.

We start at The Sears Tower and learn about “the architectural equivalent of the moon landing”, the innovative design and construction of what would be the tallest building in the world for 25 years. The saga of The Sears Tower’s naming rights and a strange instance of the heated sidewalks electrocuting two pedestrians will also be told.

Strolling down Adams and past Federal Plaza, we turn on State Street, Chicago’s original downtown strip of retail, hotels and businesses. Here we tour the Palmer House and Marshall Field building. Taking a left on Randolph, we approach City Hall, Daley Plaza and The United Methodist Church. Heading down Washington, toward the river, we have a view of the River Center, Daniel Burnham’s last project and home to Twitter and Uber’s Chicago headquarters. As we make our way back toward the Willis Tower, we will get a view of the Civic Opera House and conclude right where we started.

Meeting Point: Will be meet at the Willis Tower at the corner of Jackson Boulevard and Wacker Drive.  Here is a Google maps link.

Start Time: We run this tour at 10am on Monday, Tuesdays & Fridays. Check our calendar and Reserve Online today.

Distance: 1.7 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

  • Willis Tower
  • Rookery Building
  • Chicago Board of Trade
  • Federal Plaza
  • Marquette Building
  • Citadel Center
  • Palmer House Hotel
  • Marshall Field’s Building(s)
  • Daley Center
  • Lyric Opera House
  • CME Center

Stories you will be told: 

    • Electrocuting sidewalks of the Willis Tower
    • Sears Tower or Willis Tower?
    • America’s first futures exchange
    • Mies van der Rohe’s architectural philosophy
    • Palmer House Brownie
    • The birth of Modern Retail ..in Chicago
    • Picasso comes to Chicago

  • The legend of the Lyric Opera House
  • The future of The Loop

Chicago Walking Tours: Michigan Avenue & Millennium Park Walking Tour

Chicago Walking Tours Mich Ave Chicago Walking Tours Mich Ave Chicago Walking Tours Mich Ave

Two of Chicago’s most popular tourists destinations in one tour. Follow Michigan Avenue south from where it all started for Chicago checking out the incredible views of the Chicago River, the incredible Carbide & Carbon building and experience Millennium Park

Starting at one of Chicago’s most beautiful buildings – the Wrigley Building and heading south along Michigan Avenue through Millennium Park and ending at the picturesque Buckingham Fountain there is something for everyone on this tour. Definitely bring your camera on this tour!

Meeting Point:  Outside the The Wrigley Building (400-410 N Michigan Ave, Chicago, IL 60611Google Maps

Start Time: We run this tour at 2pm. Check our calendar and Reserve Online today.

Distance: 1.5 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

    • The Wrigley Building
    • Tribune Tower
    • Chicago River
    • Trump Tower
    • Carbide & Carbon Building
    • Chicago Cultural Center
    • Cloud Gate
    • Wrigley Monument
    • Crown Fountain
    • Buckingham Fountain

Stories you will be told: 

  • Wrigley Building and Tribune Tower
  • Chicago becomes a city
  • Reversal of the River
  • Fort Dearborn
  • Founding and Construction of Millennium Park
  • Chicago’s Lakefront rises out of the ashes
  • Buckingham Fountain and Queen’s Landing

Chicago Walking Tours: Lincoln Park Neighborhood Walking Tour

Chicago Walking Tours Lincoln Park Chicago Walking Tours Lincoln Park Chicago Walking Tours Lincoln Park

Lincoln Park has come a long way from it’s humble beginnings as a working-class neighborhood in the 1870s. Today the neighborhood is home to the best restaurants, incredible shopping, beautiful and historic residential neighborhoods and of course Lincoln Park – with FREE activities including the Lincoln Park Zoo, Lincoln Park Conservatory and Alfred Caldwell Lily Ponds. Let our guides show you the best of the best in Lincoln Park.

Meeting Point: Northeast corner of Armitage & Halsted in front of Citi Bank. Google Maps

Start Time: We run this tour sparingly. Check our calendar and Reserve Online today.

Distance: 1.8 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

    • Historic Armitage-Halsted District
    • Oz Park
    • Historic Mid-North Residential District
    • Wood-frame homes that survived the Chicago Fire
    • Alfred Caldwell Lily Pond
    • Lincoln Park
    • Lincoln Park Conservatory
    • Lincoln Park Zoo

Stories you will be told: 

      • History of Lincoln Park neighborhood
      • German immigrants influence on the look and feel
      • Creating Oz Park
      • The Great Chicago Fire of 1871
      • Introduction to famed architect Louis B. Sullivan

    • The Bellinger House
    • Creating the Lily Ponds

Chicago Walking Tours: Magnificent Mile Walking Tour

Chicago Walking Tours Mag MileChicago Walking Tours Mag MileChicago Walking Tours Mag Mile

The Magnificent Mile is the Shopping Center of the city – the 2nd largest shopping district in the United States behind only New York City’s 5th Avenue. And while it’s hard to escape a visit to the Mag Mile without spending a dime, there is much more than shopping here.

Chicago’s Magnificent Mile is home to an amazing history – from Chicago’s humble beginnings as a swamp, to buildings still standing after surviving the Great Chicago Fire of 1871 & some of Chicago’s most significant architectural feats.

See a side of the Mag Mile you have never before on our Magnificent Mile tour today!

Meeting Point:  Hard Rock Hotel (Carbon & Carbide Building). (230 N Michigan Ave, Chicago, IL 60601) Google Maps

Start Time: We start this tour at 4pm on Wednesdays & Sundays. Check our calendar and Reserve Online today.

Distance: 1.7 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

  • Carbon & Carbide Building
  • Dusable Bridge
  • Wrigley Building
  • Tribune Tower
  • The Magnificent Mile Shopping District
  • Intercontinental Hotel
  • 4th Presbyterian Church of Chicago
  • John Hancock Center
  • Lake Michigan and Oak St. Beach
  • Oak St. boutiques
  • Rush St. Restaurants

Stories you will be told: 

  • The origin of Chicago
  • The Chicago Fire
  • Reversing the flow of the river
  • Jean Baptiste Point Dusable
  • The story behind the name of the city
  • The explanation behind the Chicago flag
  • The epic of the deep dish pizza
  • The history of the playboy mansion in Chicago

Chicago Walking Tours: Chicago Crime & Gangster Tour

Chicago Crime & Gangster Tour

“Freeze!”

You have heard all of the household names before – Al Capone, Dean O’Banion, George “Bugs” Moran, “Machine Gun” Jack McGurn and Sam Giancana. But do you know what the Beer Wars were? Or where Schofield’s Flower Shop was located? Let our resident Crime and Gangster expert tour guide take you on walk through Chicago’s storied criminal past on this fun and educational walking tour through River North and Chicago’s Loop.

Starting at the picturesque and historic Old Water Tower at the corner of Chicago & Michigan Avenue, our Chicago Crime & Gangster tour will clear the air on what really went down in Chicago during the roaring 20s and after.

Wind your way through the River North area learning about the multiple gangs and their leaders that were vying for a piece of the Prohibition pie.

Stops at LaSalle Street Bridge and the Chase Tower will help explain how all of these characters crossed paths and shaped the future of Chicago.

You can’t get a more fitting end to the tour than Chicago’s Federal Plaza, a place that represents law and order, and which was the site of Al Capone’s trial and conviction and is now home to one of Chicago’s most iconic pieces of public art – Calder’s Flamingo.

 

Meeting Point: Old Water Tower – Corner of Chicago & Michigan Avenue. Google Maps

Start Time: We start this tour at 2pm on Saturdays. Check our calendar and Reserve Online today.

Distance: 2.1 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

  • Old Chicago Water Tower
  • Holy Name Cathedral
  • Former location of the Celano Tailor Shop
  • The James Hotel
  • LaSalle Street Bridge
  • Chicago River
  • Chase Tower
  • Federal Plaza

Stories you will be told: 

  • How the gangsters of Chicago became millionaires from the Volstead Act
  • Why you shouldn’t double cross Johnny the Fox
  • What a “Chicago Handshake” is
  • Where the Perfume Bandit got his name
  • The Story of “Machine Gun” Jack McGurn
  • The Office gets bugged
  • How “Trunk Music” is better left unheard
  • Al Capone’s Trial & Conviction
  • Why Family Secrets are better kept quietly

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