The Greatest Books of All Time Set in Chicago

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This list represents a comprehensive and trusted collection of the greatest books. Developed through a specialized algorithm, it brings together 759 'best of' book lists to form a definitive guide to the world's most acclaimed books. For those interested in how these books are chosen, additional details can be found on the rankings page.

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Rank Book Authors Year Country Language Actions
41 On the Road Jack Kerouac 1957 American English
107 Native Son Richard Wright 1940 American English
183 The Jungle Upton Sinclair 1906 American English
185 U.S.A. Trilogy John Dos Passos 1930 American English
280 The Adventures of Augie March Saul Bellow 1953 American English
298 Herzog Saul Bellow 1964 American English
336 Sister Carrie Theodore Dreiser 1900 American English
437 Passing Nella Larsen 1929 American English
587 The Man with the Golden Arm Nelson Algren 1949 American English
640 Black Boy Richard Wright 1945 American English
666 Humboldt's Gift Saul Bellow 1975 American English
874 The Last Samurai Helen DeWitt 2000 American English
909 The Warmth Of Other Suns Isabel Wilkerson 2010 American English
1222 Studs Lonigan James T. Farrell 1932 American English
1262 Maud Martha Gwendolyn Brooks 1953 American English
1491 Presumed Innocent Scott Turow 1987 American English
1542 The Devil In The White City Erik Larson 2003 American English
1582 Quicksand Nella Larsen 1928 American English
1634 The House on Mango Street Sandra Cisneros 1984 American English
1640 The Asphalt Jungle W. R. Burnett 1949 American English
1675 The Time Traveler's Wife Audrey Niffenegger 2003 American English
1783 A Heartbreaking Work of Staggering Genius Dave Eggers 2000 American English
1983 The Great Believers Rebecca Makkai 2018 American English
2142 Home Sweet Homicide Craig Rice 1944 American English
2192 American Gods Neil Gaiman 2001 British English
2206 Dreams from My Father Barack Obama 1995 American English
2249 Twenty Years at Hull-House Jane Addams 1910 American English
2340 Jimmy Corrigan, the Smartest Kid on Earth Chris Ware 2000 American English
2554 Dangling Man Saul Bellow 1944 American English
2630 The Resistible Rise of Arturo Ui Bertolt Brecht 1941 German German
2708 The Help Kathryn Stockett 2009 American English
2834 The Unpleasant Profession Of Jonathan Hoag Robert A. Heinlein 1942 American English
2881 Physics And Beyond Werner Heisenberg 1971 German German
2965 Kane and Abel Jeffrey Archer 1979 British English
3067 Caramelo Sandra Cisneros 2002 American English
3232 Freakonomics Steven D. Levitt, Stephen J. Dubner 2005 American English
3250 Endless Love Scott Spencer 1979 American English
3258 The 42nd Parallel John Dos Passos 1930 American English
3299 The Red Record Ida B. Wells 1895 American English
3315 City Of Night John Rechy 1963 American English
3470 Little Caesar W. R. Burnett 1929 American English
3493 Laura Vera Caspary 1943 American English
3573 Notes from No Man's Land Eula Biss 2009 American English
3630 Really The Blues Bernard Wolfe, Milton Mezz Mezzrow 1946 American English
3637 The Jazz Book Joachim-Ernst Berendt 1953 German German
3637 New Testament And Mythology Rudolf Bultmann 1941 German German
4309 Brewster's Millions Richard Greaves 1902 British English
4369 More Die Of Heartbreak Saul Bellow 1987 American English
4458 The Truly Disadvantaged William Julius Wilson 1987 American English
4664 Building Stories Chris Ware 2012 American English
4720 A History Of Religious Ideas, Volume 3 Mircea Eliade 1985 French French
5004 Against the Day Thomas Pynchon 2006 American English
5036 Eight Men Richard Wright 1961 American English
5037 Storm Front Jim Butcher 2000 American English
5187 The Professor Challenger Stories Arthur Conan Doyle 1912 British English
5348 A Street In Bronzeville Gwendolyn Brooks 1945 American English
5357 Team of Rivals Doris Kearns Goodwin 2005 American English
5360 The Hite Report Shere Hite 1976 American English
5472 Working Studs Terkel 1974 American English
5595 The Lazarus Project Aleksandar Hemon 2008 Bosnian English
5631 Sabrina Nick Drnaso 2018 American English
5935 The Spiral Of Silence Elisabeth Noelle-Neumann 1982 German German
5997 King Jonathan Eig 2023 American English
6002 Testimony Charles Reznikoff 1965 American English
6127 Negroland Margo Jefferson 2015 American English
6512 The Control Revolution James R. Beniger 1986 American English
6528 The Hating Game Sally Thorne 2016 Australian English
6567 Toxic Shock Sara Paretsky 1988 American English
6581 Hardball Sara Paretsky 2009 American English
6686 Ravelstein Saul Bellow 2000 American English
6835 There Are No Children Here Alex Kotlowitz 1991 American English
6872 Eustace Chisholm And The Works James Purdy 1967 American English
6937 Century Of Struggle Eleanor Flexner 1959 American English
7062 Then We Came To The End Joshua Ferris 2007 American English
7078 Aquamarine Carol Anshaw 1992 American English
7122 Why We Love Helen Fisher 2004 American English
7142 Hello Beautiful Ann Napolitano 2023 American English
7163 A Million Little Pieces James Frey 2003 American English
7681 Left Behind Tim LaHaye, Jerry B. Jenkins 1995 American English
7784 The Wig Charles Wright 1966 American English
7857 Jennie Gerhardt Theodore Dreiser 1911 American English
8181 Dead Time Eleanor Taylor Bland 1992 American English
8232 The Promised Land Nicholas Lemann 1991 American English
8283 Nowhere Man Aleksandar Hemon 2002 Bosnian English
8307 How The Light Gets In M. J. Hyland 2003 Australian English
8322 American Buffalo David Mamet 1975 American English
8461 Griftopia Matt Taibbi 2010 American English
8461 Being Wrong Kathryn Schulz 2010 American English
8486 The Book Of My Lives Aleksandar Hemon 2013 American English
8570 Let The Trumpet Sound Stephen B. Oates 1982 American English
8591 The Adventures Of Tintin Hergé 1929 Belgian French
8697 Blacklist Sara Paretsky 2003 American English
8794 It Happened One Wedding Julie James 2014 American English
8849 I Am Homeless If This Is Not My Home Lorrie Moore 2023 American English
8865 Crisis Of The House Divided Harry V. Jaffa 1959 American English
8923 How Children Succeed Paul Tough 2012 Canadian English
8970 The Dean's December Saul Bellow 1982 American English
8993 A Stir Of Echoes Richard Matheson 1958 American English
9139 Talk Before Sleep Elizabeth Berg 1994 American English
9176 Beautiful Bastard Christina Lauren 2013 American English
9176 Off To Be The Wizard Scott Meyer 2013 English
9188 How We Got To Now Steven Johnson 2014 American English
9188 But What If We're Wrong? Chuck Klosterman 2016 American English
9233 Primal Fear William Diehl 1993 American English
9284 Brutal Prince Sophie Lark 2020 Unknown English
9318 The Beautiful Room Is Empty Edmund White 1988 American English
9321 The Hacker Crackdown Bruce Sterling 1992 American English
9325 In Search Of Excellence Tom Peters, Robert H. Waterman, Jr. 1982 American English
9337 Rails Under My Back Jeffery Renard Allen 2000 American English
9566 Pucked Helena Hunting 2015 Canadian English
9609 The Three Paradoxes Paul Hornschemeier 2007 American English
9617 We Are Never Meeting In Real Life. Samantha Irby 2017 American English
9708 The Dispatcher John Scalzi 2016 American English
9769 The Night Bookmobile Audrey Niffenegger 2010 American English
9938 Crusade For Justice Ida B. Wells 1970 American English
10057 Wellness Nathan Hill 2024 American English
10073 The Body Project Joan Jacobs Brumberg 1997 American English
10153 So Big Edna Ferber 1924 American English
10234 Race For Profit Keeanga-Yamahtta Taylor 2019 American English
10303 Street Games Rosellen Brown 1974 American English