Free Walking Sightseeing Tours in Chicago, United States

Legend

Self-guided Tours
Paid Tours & Activities

Are you ready for an unforgettable time in Chicago, United States? Then you've come to the right place with our sightseeing tours. Whether you prefer a guided free walking tour with insider knowledge or enjoy the freedom of a self-guided route, you'll find exactly what you're looking for. Click on a tour and find out more about the highlights that await you!

Individual Sights in Chicago

Self-guided Tour #1

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Number of sights 7 sights
Distance 1.3 km
Ascend 7 m
Descend 7 m

  • Austin Town Hall Park
  • Seth Warner House
  • Hitchcock House
  • Schlect House
  • Marie Schock House
  • F. R. Schock House
  • Beeson House
Details for Tour #1 in Chicago

Self-guided Tour #2

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Number of sights 13 sights
Distance 3.2 km
Ascend 345 m
Descend 164 m

  • Chicago Avenue Pumping Station
  • Chicago Water Tower
  • Loyola University Museum of Art
  • Holy Name Cathedral
  • Washington Square
  • Allow Me
  • Palmolive Building
  • The Drake Hotel
  • 360 Chicago
  • Broadway Playhouse at Water Tower Place
  • Chicago Sports Museum
  • Museum of Contemporary Art
  • 860 Lake Shore Drive
Details for Tour #2 in Chicago

Self-guided Tour #3

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Number of sights 29 sights
Distance 8.8 km
Ascend 759 m
Descend 749 m

  • Mark Twain Hotel
  • Church of the Ascension
  • Annunciation Greek Orthodox Cathedral
  • Washington Square
  • Palette and Chisel
  • Mariano Park
  • Fortnightly of Chicago
  • The Drake Hotel
  • Palmolive Building
  • Allow Me
  • 360 Chicago
  • Broadway Playhouse at Water Tower Place
  • 860 Lake Shore Drive
  • Chicago Sports Museum
  • Museum of Contemporary Art
  • Chicago Avenue Pumping Station
  • Chicago Water Tower
  • Loyola University Museum of Art
  • Holy Name Cathedral
  • St. James Episcopal Cathedral
  • Nickerson House
  • Richard H. Driehaus Museum
  • Ransom R. Cable House
  • Former Chicago Historical Society Building
  • Former Medinah Temple
  • Chicago Riverwalk
  • Crossing
  • Constellation
  • Chicago and North Western Railway Power House
Details for Tour #3 in Chicago

Self-guided Tour #4

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Number of sights 14 sights
Distance 4.9 km
Ascend 135 m
Descend 123 m

  • Seward Park
  • Marshall Hotel
  • Mark Twain Hotel
  • Church of the Ascension
  • Annunciation Greek Orthodox Cathedral
  • Washington Square
  • Palette and Chisel
  • Mariano Park
  • Fortnightly of Chicago
  • Charnley-Pesky House Museum
  • International Museum of Surgical Science
  • Abraham Lincoln: The Man
  • Chicago History Museum
  • The Second City
Details for Tour #4 in Chicago

Self-guided Tour #5

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Number of sights 6 sights
Distance 2.2 km
Ascend 18 m
Descend 20 m

  • Briar Street Theatre
  • Legacy Walk Rainbow Pylon
  • The Playground Theater
  • Anshe Sholom Bnai Israel Congregation
  • Temple Sholom
  • Kwa-Ma-Rolas (Totem Pole)
Details for Tour #5 in Chicago

Self-guided Tour #6

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Number of sights 5 sights
Distance 1.9 km
Ascend 12 m
Descend 16 m

  • Black Ensemble Theater
  • Buddhist Temple of Chicago
  • Riviera Theatre
  • Byline Bank Aragon Ballroom
  • Uptown Theatre
Details for Tour #6 in Chicago

Self-guided Tour #7

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Number of sights 30 sights
Distance 11.7 km
Ascend 848 m
Descend 832 m

  • Milton Lee Olive Park
  • Ogden Plaza
  • Chicago Rising from the Lake
  • Jack Brickhouse
  • McCormick Bridgehouse & Chicago River Museum
  • Chicago Riverwalk
  • Seventeenth Church of Christ Scientist
  • Heald Square Monument
  • Page Brothers Building
  • Chicago Theatre
  • James M. Nederlander Theatre
  • Albert Ivar Goodman Theatre
  • Owen Bruner Goodman Theatre
  • Monument With Standing Beast
  • Cadillac Palace Theatre
  • Loop Synagogue
  • Residence Inn Chicago Downtown/Loop
  • Civic Opera House
  • Chicago Union Station
  • National Hellenic Museum
  • Greektown
  • Haymarket Memorial
  • Chicago and North Western Railway Power House
  • Constellation
  • Crossing
  • Former Chicago Historical Society Building
  • Ransom R. Cable House
  • Richard H. Driehaus Museum
  • Nickerson House
  • Former Medinah Temple
Details for Tour #7 in Chicago

Self-guided Tour #8

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Number of sights 5 sights
Distance 2 km
Ascend 19 m
Descend 19 m

  • U-505 Submarine
  • Pioneer Zephyr
  • Griffin Museum of Science and Industry
  • Jackson Park
  • Midway Plaisance
Details for Tour #8 in Chicago

Self-guided Tour #9

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Number of sights 18 sights
Distance 7.4 km
Ascend 795 m
Descend 812 m

  • Grant Park
  • Seventeenth Church of Christ Scientist
  • Chicago Riverwalk
  • Heald Square Monument
  • Vietnam Veterans Memorial
  • Irv Kupcinet
  • Chicago Architecture Center
  • McCormick Bridgehouse & Chicago River Museum
  • Jack Brickhouse
  • Chicago Rising from the Lake
  • Ogden Plaza
  • Nicholas J. Melas Centennial Fountain
  • Polk Bros Park
  • Captain on the Helm
  • Chicago Children's Museum
  • Chicago Shakespeare Theater
  • Navy Pier
  • Milton Lee Olive Park
Details for Tour #9 in Chicago

Self-guided Tour #10

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Number of sights 20 sights
Distance 8.6 km
Ascend 440 m
Descend 422 m

  • Jane Addams Park
  • Maxwell Street
  • UIC Skyspace
  • Pillar of Fire
  • Hotel Roosevelt
  • Ludington Building
  • Fairbanks Morse Building
  • 8th Street Fountain
  • Spirit of Music (Theodore Thomas Memorial)
  • Merle Reskin Theatre
  • Magdalene
  • Equestrian Indians (The Bowman)
  • Grant Park
  • Clarence Buckingham Memorial Fountain
  • Hector Guimard Metro entrance
  • Fine Arts Building
  • Auditorium Theatre
  • Manhattan Building
  • Old Colony Building
  • San Marco II
Details for Tour #10 in Chicago

Self-guided Tour #11

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Number of sights 20 sights
Distance 8.9 km
Ascend 185 m
Descend 173 m

  • Leonard M. Louie
  • Soka Gakkai International Buddhist Center
  • Coca-Cola Building
  • Rosenberg Fountain (Hebe)
  • Crane Company Building
  • John Alexander Logan Monument
  • Brachiosaurus Replica
  • Big Beaver Totem Pole
  • Sue the Dinosaur
  • Field Museum
  • Italo Balbo Monument
  • Huntington Bank Pavilion at Northerly Island
  • Man Enters The Cosmos
  • Adler Planetarium
  • Nicolaus Copernicus Monument
  • Karel Havlíček Monument
  • Tadeusz Kościuszko Monument
  • Man with Fish
  • Olmec Head
  • Grant Park
Details for Tour #11 in Chicago

Self-guided Tour #12

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Number of sights 30 sights
Distance 13.6 km
Ascend 1009 m
Descend 1006 m

  • Columbia Yacht Club (Q.S.M.V. Abegweit)
  • Maggie Daley Park
  • Joan W. and Irving B. Harris Theater for Music and Dance
  • Jay Pritzker Pavilion
  • Millennium Park
  • Cloud Gate
  • Cow
  • Lion on the prowl
  • Cubi VII
  • Lurie Garden
  • Chicago Stock Exchange Arch
  • Grant Park
  • Fine Arts Building
  • Chicago L
  • Manhattan Building
  • Money Museum
  • Calder's Flamingo
  • CIBC Theatre
  • Four Seasons
  • Loop Synagogue
  • Miro's Chicago
  • Chicago Picasso
  • Albert Ivar Goodman Theatre
  • Owen Bruner Goodman Theatre
  • Chicago Theatre
  • Cadillac Palace Theatre
  • Civic Opera House
  • Chicago Union Station
  • Greektown
  • Pillar of Fire
Details for Tour #12 in Chicago

Self-guided Tour #13

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Number of sights 30 sights
Distance 13.7 km
Ascend 1564 m
Descend 1566 m

  • Columbia Yacht Club (Q.S.M.V. Abegweit)
  • Maggie Daley Park
  • Joan W. and Irving B. Harris Theater for Music and Dance
  • Jay Pritzker Pavilion
  • Millennium Park
  • Cloud Gate
  • Cow
  • Fountain of the Great Lakes
  • Lion on the prowl
  • Cubi VII
  • Lurie Garden
  • Chicago Stock Exchange Arch
  • James C. Petrillo Music Shell
  • Grant Park
  • Sir Georg Solti Bust
  • Chicago L
  • Money Museum
  • Calder's Flamingo
  • CIBC Theatre
  • Four Seasons
  • Miro's Chicago
  • Chicago Picasso
  • Chicago Riverwalk
  • Chicago Architecture Center
  • Nicholas J. Melas Centennial Fountain
  • Captain on the Helm
  • Chicago Children's Museum
  • Chicago Shakespeare Theater
  • Navy Pier
  • Milton Lee Olive Park
Details for Tour #13 in Chicago

Self-guided Tour #14

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Number of sights 11 sights
Distance 5 km
Ascend 82 m
Descend 87 m

  • Café Brauer (South Pond Refectory)
  • Ulysses S. Grant Monument
  • Benjamin Franklin
  • Robert Cavalier de LaSalle
  • Chicago History Museum
  • Abraham Lincoln: The Man
  • International Museum of Surgical Science
  • The Second City
  • Hery Gerber House
  • Saint Michael Roman Catholic Church
  • iO Theater
Details for Tour #14 in Chicago

Self-guided Tour #15

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Number of sights 5 sights
Distance 2.3 km
Ascend 22 m
Descend 22 m

  • Saint John Cantius Roman Catholic Church
  • Intuit: The Center for Intuitive and Outsider Art
  • Polish Museum of America
  • Former Elizabeth Peabody School
  • Holy Innocents Catholic Church
Details for Tour #15 in Chicago

Self-guided Tour #16

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Number of sights 11 sights
Distance 5.3 km
Ascend 71 m
Descend 78 m

  • St. Vincent de Paul Catholic Church
  • Biograph Theatre
  • Saint Clement Roman Catholic Church
  • Reebie Storage & Moving Co
  • The Peggy Notebaert Nature Museum
  • Richard Oglesby Monument
  • Alexander Hamilton Monument
  • John Peter Altgeld Momument
  • Lincoln Park
  • A Signal of Peace
  • The Alarm
Details for Tour #16 in Chicago

Self-guided Tour #17

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Number of sights 6 sights
Distance 3 km
Ascend 27 m
Descend 26 m

  • Holy Trinity Catholic Church
  • Chopin Theatre
  • Holy Trinity Russian Orthodox Cathedral
  • Ukrainian Institute of Modern Art
  • Saints Volodymyr and Olha Catholic Church
  • Ukrainian National Museum
Details for Tour #17 in Chicago

Self-guided Tour #18

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Number of sights 12 sights
Distance 6.3 km
Ascend 64 m
Descend 63 m

  • U-505 Submarine
  • Pioneer Zephyr
  • Griffin Museum of Science and Industry
  • Jackson Park
  • Frederick C. Robie House
  • First Unitarian Church of Chicago
  • Saint Thomas the Apostle Catholic Church
  • David and Alfred Smart Museum of Art
  • Nuclear Energy
  • Midway Plaisance
  • Fountain of Time
  • Washington Park
Details for Tour #18 in Chicago

Self-guided Tour #19

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Number of sights 9 sights
Distance 4.8 km
Ascend 93 m
Descend 81 m

  • Leonard M. Louie
  • Soka Gakkai International Buddhist Center
  • Coca-Cola Building
  • Hotel Roosevelt
  • Big Beaver Totem Pole
  • Olmec Head
  • Field Museum
  • Man with Fish
  • Grant Park
Details for Tour #19 in Chicago

Self-guided Tour #20

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Number of sights 8 sights
Distance 4.3 km
Ascend 40 m
Descend 37 m

  • Stephen A. Douglas Tomb
  • Bronzeville
  • Victory Monument
  • Haymarket Police Memorial
  • Overton Hygienic Building
  • Carr Memorial Chapel
  • Dunbar Park
  • Olivet Baptist Church
Details for Tour #20 in Chicago

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Why Visit Sights? Self-guided sightseeing tours are a free and safe alternative to bus tours. You can explore Chicago at your own pace, any time! Do something good for your health by walking.