| Known For | Answer | % Correct |
|---|---|---|
| Notorious Gangster | Al Capone | 92%
|
| Chicago Bulls / Sneakers | Michael Jordan | 83%
|
| Former U.S. President | Barack Obama | 79%
|
| Mickey Mouse | Walt Disney | 77%
|
| Secretary of State / First Lady | Hillary Clinton | 69%
|
| Media Executive and Talk-show Host | Oprah Winfrey | 69%
|
| Chicago Mayor / Democratic National Convention | Richard J. Daley | 69%
|
| Longest Serving Chicago Mayor | Richard M. Daley | 69%
|
| Chewing Gum | William Wrigley Jr. | 69%
|
| World Renowned Architect / Prairie School | Frank Lloyd Wright | 63%
|
| A Farewell to Arms | Ernest Hemingway | 62%
|
| Movie Critic | Roger Ebert | 54%
|
| Fahrenheit 451 | Ray Bradbury | 50%
|
| "Mr. Cub" | Ernie Banks | 48%
|
| Illinois Senator / Lincoln Rival | Stephen A. Douglas | 46%
|
| Physicist / Creator of First Nuclear Reactor | Enrico Fermi | 44%
|
| Hull House | Jane Addams | 40%
|
| Nation of Islam Leader | Louis Farrakhan | 40%
|
| First African-American Mayor | Harold Washington | 38%
|
| Civil Rights Activist / Minister / Politician | Jesse Jackson Sr. | 38%
|
| "Papa Bear" | George Halas | 37%
|
| Prominent Lawyer / Scopes Trial | Clarence Darrow | 29%
|
| Department Stores / Philanthropy | Marshall Field | 29%
|
| Chicago Blues | Muddy Waters | 27%
|
| Poet and Lincoln Biographer / "City of Big Shoulders" | Carl Sandburg | 25%
|
| Inventor / Mechanical Reaper | Cyrus McCormick | 25%
|
| Newspaper Magnate | Robert R. McCormick | 25%
|
| Socialist Party of America | Eugene V. Debs | 23%
|
| "Founder of Chicago" | Jean Baptiste Point DuSable | 23%
|
| Conservative Economist | Milton Friedman | 23%
|
| Magazine Publisher | Hugh Hefner | 21%
|
| Nation of Islam / Mentor to Malcolm X and Muhammad Ali | Elijah Muhammad | 17%
|
| Mid-20th Century Progressive Politician | Adlai Stevenson II | 15%
|
| First Female African-American Senator | Carol Moseley Braun | 15%
|
| Posthumous Icon of the Civil Rights Movement | Emmett Till | 15%
|
| World's Columbian Exposition Architect | Daniel Burnham | 13%
|
| Doomed Industrialist / Worker Strikes | George Pullman | 13%
|
| "Father of Skyscrapers" | Louis Sullivan | 13%
|
| Two-time Secretary of Defense / Conservative Politician | Donald Rumsfeld | 12%
|
| Black Panther Party | Fred Hampton | 12%
|
| Modernist Architecture | Ludwig Mies van der Rohe | 12%
|
| Journalist / NAACP Co-founder | Ida B. Wells | 10%
|
| Pragmatism | John Dewey | 8%
|
| The Man With the Golden Arm | Nelson Algren | 8%
|
| Fiction Writer / Three National Book Awards | Saul Bellow | 8%
|
| Meat Industry Magnate | Gustavus Swift | 6%
|
| King of Soul | Sam Cooke | 6%
|
| Blues and Rock and Roll Pioneer | Bo Diddley | 2%
|
| Sears Department Stores / Philanthropy | Julius Rosenwald | 2%
|
| Electrical Infrastructure | Samuel Insull | 0%
|