Essential Chicago: A Self-Guided Walking Tour of the Loop, River & Skyline Essential Chicago is a first-timer's flagship walk through downtown Chicago. This tour covers twenty-five stops and a dozen longer chapters, running from the Wrigley Building and DuSable Bridge at the river, south through the Loop to Millennium Park and the Art Institute, and west to Willis Tower. It is a self-guided audio tour, so you set the order and the pace. About This Self-Guided Walking Tour of Chicago Chicago engineers reversed the direction of the Chicago River to protect the city's water supply. The early sewers emptied into the river, the river ran toward Lake Michigan, and Lake Michigan was where Chicago drew most of its drinking water. That reversal is one of twenty-five stops on this tour. Long before an American city stood here, travelers used a short portage beside the river to move between the Great Lakes and the Mississippi watershed, because the Chicago River sits beside a low continental divide. Canal companies and then railroad companies made that crossing permanent, and by the late nineteenth century traders were pricing the grain of half a continent within a few blocks of the river mouth. Land inside that small commercial district grew expensive enough that Chicago architects had to work out how to build tall, and the Reliance Building, the Monadnock Block and the Rookery are three of their answers. The Great Chicago Fire began on the evening of October 8, 1871 near the O'Leary property on DeKoven Street, and twenty-two years after it burned through the center of the city, Chicagoans staged the World's Columbian Exposition to claim a place among the world's great metropolitan centers. The people who did the building pressed their own claim on the same ground. In the spring of 1886, tens of thousands of Chicagoans joined a national movement for the eight-hour workday and walked off jobs that ran to punishing lengths in dangerous conditions. Over the following half century, hundreds of thousands of Black southerners left Jim Crow segregation and racial terror for Chicago, and they changed who the downtown belonged to. The Route: River, Loop and Skyline in Downtown Chicago Wrigley Building : William Wrigley Jr. put his chewing-gum headquarters on this riverfront corner just as developers were remaking North Michigan Avenue around the new bridge.Tribune Tower : the Chicago Tribune ran a 1922 competition for what the paper called the world's most beautiful office building, and more than 260 entries arrived from twenty-three countries.DuSable Bridge : a crossing on land the Chicago History Museum identifies as ancestral Potawatomi homeland, where Indigenous people lived and traded long before an American city stood here.Chicago Riverwalk : the downtown waterfront that carried ships and factories before planners rebuilt it as a landscaped promenade.Marina City : Bertrand Goldberg's answer to postwar suburban growth, a dense downtown development where people could live close to work.Chicago Theatre : Rapp & Rapp's 1921 movie palace, from the years when going to the pictures meant a grand lobby and live musical accompaniment.Loop Elevated at State and Lake : where companies connected their elevated tracks in 1897 and gave the Loop its name.Daley Center and the Picasso : a 1960s civic center of weathering steel and dark glass, with Picasso's untitled sculpture standing on its open plaza.Reliance Building and Sullivan Center : an 1890s building whose metal frame carries the weight, so the outer walls open into broad bays of glass, and Louis Sullivan's elaborate street-level work at State and Madison.Monadnock Block and the Rookery : Burnham & Root settling, in two very different buildings, what a tall commercial building should be.Chicago Cultural Center : the city's central public library when it opened in 1897, with marble and mosaic lavished on public space.Millennium Park, Cloud Gate and Crown Fountain : parkland decked over the railroad tracks that ran along this edge of downtown for generations.Art Institute of Chicago : opened on Michigan Avenue in the year of the 1893 world's fair, when Chicago's business leaders wanted an industrial city taken seriously.Auditorium Building and Fine Arts Building : a grand opera house that had to earn its keep, and a Studebaker carriage works converted in 1898 for a very different clientele.Willis Tower : Sears, Roebuck and Company built it to gather its Chicago offices under one roof. You'll Learn About… Who Robert Morris and Haym Salomon were, and why Chicago civic leaders raised the money to stand them in bronze beside George Washington at Heald Square.Why the northern half of the Monadnock Block could only rise so far: Burnham & Root carried it on load-bearing brick walls, and there is a hard ceiling on how tall load-bearing brick can go.What Ida B. Wells was doing as an editor and newspaper owner in Memphis, and how she built a national anti-lynching campaign after three Black businessmen were murdered there.How Jane Addams and Ellen Gates Starr opened Hull-House on the Near West Side in 1889, on her idea that reform required proximity.How Edward Bennett and the Commercial Club shaped the 1909 Plan of Chicago that everyone now calls the Burnham Plan.Why U.S. Route 66 has its eastern end downtown, and where the original alignment of a two-thousand-mile highway to Los Angeles began in 1926.What Louis Sullivan was arguing about the tall office building in the years when elevators had just made upper floors worth renting. Who It's For This is the flagship tour for a first-time visitor to Chicago who wants the downtown to make sense. If you have a day in the Loop and want to know why the skyline is here and who argued over the city while it was going up, start here. Travelers who read history for the people in it will find plenty at every stop. Practical Details The route runs roughly three to four miles through downtown Chicago and takes about three hours at an unhurried pace, longer with lunch or an hour inside the Art Institute. The Wrigley Building at the river makes a natural starting point, though the stops have no fixed order and you can join anywhere along the way. Everything is self-guided, so you move at your own speed. Alongside the stops there are twelve longer chapters, four of them built around the words of Chicagoans including Jane Addams and Ida B. Wells. Download the App and Take the Tour Download the app and take Essential Chicago with you, and hear each story where it happened.
