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28th International Eucharistic Congress- 1998 National League Wild Card tie-breaker game
- 2000 Illinois's 1st congressional district election
- MLS Cup 2000
- 2002 Delphi Indy 300
- MLS Cup 2003
- Tornado outbreak of October 17–19, 2007
- 2008 American League Central tie-breaker game
- 2015 Chicago Bears season
- 2018 Chicago Marathon
- 2021 Naperville–Woodridge tornado
- Isaac Adewole
- Harold Agnew
- Joe Aiello
- Vic Aldridge
- Cliff Alexander
- All Day (Kanye West song)
- All the Way (Eddie Vedder song)
- Samuel King Allison
- Luis Walter Alvarez
- American Airlines Flight 191
- Hannah Arendt
- Argo Tea
- Grainger Plaza
- Emilie Autumn
- Myrtle Bachelder
- Charlie Baker
- Scott Baker (right-handed pitcher)
- Paul Bako
- Ernie Banks
- Fanya Baron
- Michael Barrett (baseball)
- Baseball's Sad Lexicon
- Batman Begins
- Bayard–Condict Building
- Gene Bearden
- Benet Academy
- Sean Bennett (gridiron football)
- Doug Bentley
- Max Bentley
- Joseph Berrios
- The Blackstone Hotel
- Blackstone Library
- Timothy Blackstone
- Block 37
- The Blues Brothers (film)
- Boeing Galleries
- Zach Bogosian
- Frenchy Bordagaray
- Jim Bottomley
- Bound for Glory IV
- Rene Bourque
- Jay Bouwmeester
- Milton Bradley (baseball)
- Tim Breslin
- Roger Bresnahan
- Frank Brimsek
- Marion L. Brittain
- Broadway Limited
- Fawn M. Brodie
- Sergio Brown
- Willa Brown
- Brownie Mary
- Jalen Brunson
- Thomas Barbour Bryan
- Kris Bryant
- Bud Billiken Parade and Picnic
- Bungie
- Jon Burge
- Edward M. Burke
- Burnham Park (Chicago)
- Burnham Pavilions
- Pete Burnside
- Dick Butkus
- Paul Butterfield
- William Heath Byford
- Peter Bynoe
- Lynton K. Caldwell
- Canal station (CTA Metropolitan Main Line)
- Billy Cannon
- Al Capone
- Carol (film)
- Dan Castellaneta
- Susan Catania
- Gene Cernan
- Frank Chance
- Bob Chappuis
- Chase Promenade
- Chasing Vermeer
- Ava Cherry
- Chevelle (band)
- 2013 Chicago Bears season
- Chicago bid for the 2016 Summer Olympics
- Chicago Marathon
- Chicago Options Associates
- Chicago race riot of 1919
- Chicago Spire
- Chicago Theatre
- Chicago station (CTA Logan Square branch)
- Gery Chico
- Robert F. Christy
- Sandra Cisneros
- City of Denver (train)
- Allie Clark
- Stephen Colbert
- Ellis Coleman
- Sherron Collins
- The Color of Money
- J. T. Compher
- Roy Conacher
- The Cool Kids
- Paul Cornell (lawyer)
- Clint Courtney
- Chris Creighton
- George Cressey
- Patrick Henry Cronin
- Roger Crozier
- Cumberland station (CTA)
- Trent Daavettila
- Steve Dahl
- John P. Daley
- Richard M. Daley
- Damen station (CTA Blue Line)
- Alvin Dark
- Anthony Davis
- Davis Theater
- Billy DeBeck
- Adam DeBus
- DeKalb County Courthouse (Illinois)
- Joseph DeLee
- Eugene V. Debs
- Jim Delsing
- Mark DeRosa
- Paul Des Jardien
- DiDa Ritz
- Johnny Dickshot
- Elizabeth Dilling
- Divergent (novel)
- Division station (CTA Logan Square branch)
- Dick Donovan
- Maurice Douglass
- Douglass Park
- Robert Dover (equestrian)
- Moe Drabowsky
- DuSable Black History Museum and Education Center
- DuSable Bridge
- Irene Dunne
- Drake Dunsmore
- Jerry Dybzinski
- EMD F40PH
- Kenny Easley
- Roger Ebert
- Don Eddy (baseball)
- Mary Beth Edelson
- Joel Edmundson
- Huw Edwards (conductor)
- Ninian Edwards
- Christian Ehrhoff
- Electoral history of Ronald Reagan
- Eliel Saarinen's Tribune Tower design
- Rahm Emanuel
- Encyclopedia of Chicago
- Whitney Engen
- Johnny Evers
- Extreme Rules (2012)
- Fabyan Windmill
- David Falk
- Fall Out Boy
- Scott Feldman
- Bob Ferguson (infielder)
- Ferris Bueller's Day Off
- Tina Fey
- Lupe Fiasco
- Bobby Fischer
- Val Logsdon Fitch
- Mike Fontenot
- Fountain of the Great Lakes
- Jimmie Foxx
- James Franck
- Ted Frank
- Franklin Center (Chicago)
- Milton Friedman
- Fun Lounge police raid
- John Wayne Gacy
- Lloyd L. Gaines
- Lu Gambino
- Game of Change
- Mike Garcia (baseball, born 1923)
- Charlie Gardiner (ice hockey)
- Pau Gasol
- John Warne Gates
- Gerald Ratner Athletics Center
- Pretzels Getzien
- Barbara Gittings
- Go, Cubs, Go
- Erving Goffman
- Jackie Goldberg
- Irving Gottesman
- Kevin Grady
- Grand Central Station (Chicago)
- Grand station (CTA Logan Square branch)
- Curtis Granderson
- Grant Park Music Festival
- Alvin C. Graves
- The Great Ziegfeld
- Rex Grossman
- Ernest Groth
- Gary Gygax
- William P. Halliday
- Remy Hamilton
- Richard Hamming
- John Marshall Harlan II
- Harold Washington Cultural Center
- Laura Harrier
- Abram Lincoln Harris
- Gabby Hartnett
- Perry Hartnett
- David Hattner
- LaTroy Hawkins
- Kevin Hayes
- Haymarket affair
- Haystacks (Monet series)
- Bill Haywood
- Spencer Heath (baseball)
- Bobby Heenan
- Heller House
- Mitch Henderson
- Rickey Henderson
- Buck Herzog
- Devin Hester
- Jason Heyward
- Matt Hicks (basketball)
- Historic Michigan Boulevard District
- Charlie Hodes
- Holden Block
- Home Alone
- Homecoming (Kanye West song)
- Hoop Dreams
- Jett Howard
- Brett Hull
- Hull House
- Philip Humber
- Philip Humber's perfect game
- John Hummer
- Otto Frederick Hunziker
- Hyde Park Township, Illinois
- Illinois Route 22
- Inland Steel Company
- The J's with Jamie
- Jesse Jackson Jr.
- Sandi Jackson
- Jane Collective
- Wadsworth Jarrell
- Mae Jemison
- Joffrey Tower
- Tommy John
- Rashid Johnson
- Quintin Johnstone
- Jason Jones (programmer)
- Cato June
- Mike Kafka
- Elena Kagan
- Maria Kanellis
- Chief Keef
- Carson Kelly
- George Kelly (baseball)
- Pat Kelly (outfielder)
- Frances Oldham Kelsey
- Michael Kenna (politician)
- Jerry Kindall
- Don Kindt
- Kinzie Street railroad bridge
- Jason Kipnis
- Judith Krug
- Rusty Kuntz
- Lakeshore East
- Geoffrey A. Landis
- Bill Lange
- Jimmy Lavender
- Ernest Lawrence
- AJ Lee
- Hughie Lehman
- Bob Lemon
- Benjamin F. Lewis
- Willard Libby
- Jon Lieber
- Joe Lillard
- The Litigators
- Carli Lloyd
- Kenny Lofton
- Loose Fur
- Bobby Lowe
- Sid Luckman
- Lurie Children's Hospital
- Lurie Garden
- Evan Lysacek
- MLS Cup 1998
- Madison station (CTA)
- Victor Maghakian
- Magnificent Mile
- Majestic Radios
- Gerri Major
- Pat Malone
- Man Enters the Cosmos
- Man of Steel (film)
- Gus Mancuso
- John Marburger
- Marching Men
- Johnny Marcum
- Venric Mark
- Marquette Building (Chicago)
- Marshall Field and Company Building
- Pepper Martin
- Dave Martinez
- Charles Matthews (basketball)
- Marilyn Maye
- William McAndrew
- Demetri McCamey
- Joanne McCarthy (basketball)
- Josh McCown
- Keith McCready
- McDonald's Chicago Flagship
- George McGovern
- Erin McLeod
- Winsor McCay
- James McDivitt
- Meet the Parents
- Megitza
- Merle Reskin Theatre
- Midwestern University
- George Mikan
- Quincy Miller
- Patsy Mink
- Brandon Minor
- Mirth & Girth
- Milan C. Miskovsky
- Joan Mitchell
- David Molk
- Ryan Mollett
- Charlie Moore (basketball)
- E'Twaun Moore
- Bill Mosienko
- Kit Mueller
- Pete Muldoon
- John Benjamin Murphy
- Mark Murphy (American football executive)
- Museum of Contemporary Art Chicago
- My Kind of Town
- Nation of Islam
- Native American mascot controversy
- Near South Side, Chicago
- Reid Nichols
- George Nicol (baseball)
- No Mercy (2007)
- North Bank Depot Buildings
- North Coast Hiawatha
- 2008 Northern Illinois University shooting
- Northwestern Memorial Hospital
- Michelle Obama
- Phil Ochs
- Jahlil Okafor
- Bert Olmstead
- Patrick Omameh
- Victor Oreskovich
- Bobby Orr
- Dan Osinski
- J. T. O'Sullivan
- Geraldine Page
- Jim Pappin
- Colton Parayko
- Park Grill
- Anthony Parker
- Jabari Parker
- George N. Parks
- Jiggs Parrott
- Ara Parseghian
- Walter Payton
- Rob Pelinka
- People v. Aguilar
- Neifi Pérez
- Perfect Dark (2010 video game)
- Petrillo Music Shell
- David Petway
- Jeannette Piccard
- Billy Pierce
- Pill Hill (play)
- Pilot (The Playboy Club)
- Ping Tom Memorial Park
- Wally Pipp
- Amy Poehler
- Irving Kane Pond
- Willis J. Potts
- Toni Preckwinkle
- LeRoy Prinz
- Prison Break
- Penny Pritzker
- Pui Tak Center
- Pulaski station (CTA Orange Line)
- Radioland Murders
- Rainbow/PUSH
- Megan Rapinoe
- Jerry Reinsdorf
- Robert V. Remini
- The Reputation
- Rise Against
- Garland Rivers
- Road to Perdition
- Roanoke Building
- Dennis Rodman
- Jimmy Rollins
- Rookery Building
- Ned Rorem
- Arnold Ross
- Gunther E. Rothenberg
- Aaron Rowand
- Rush Street (Chicago)
- Lou Saban
- Lawrence Sabatini
- Sauganash Hotel
- Gale Sayers
- Scarface (1932 film)
- Jon Scheyer
- Nate Schierholtz
- O'Brien Schofield
- Jordan Schroeder
- Arthur Schultz
- Schulze Baking Company Plant
- Schwa (restaurant)
- Stuart Scott
- Louis J. Sebille
- Second Generation (advertisement)
- Pat Seerey
- Sense8
- Alex Seropian
- Orator Shafer
- Clark Shaughnessy
- James Shields (politician, born 1806)
- Helen Shiller
- John Shurna
- Silver Springs State Fish and Wildlife Area
- Josh Sims (lacrosse)
- Sixteen (restaurant)
- Cyril Stanley Smith
- Patti Smith
- Society for Human Rights
- Spider-Man 2
- William A. Spinks
- Spirit Fruit Society
- Joseph Staten
- Statue of Michael Jordan
- Statue of Nathan Hale (Chicago)
- Bill Stein
- Jack Stewart (ice hockey)
- Bernard Stone
- John Stossel
- Streeterville
- Tai Streets
- Elmer Stricklett
- Matt Striebel
- SummerSlam (1994)
- Billy Sunday
- Eric Surkamp
- Gary Suter
- Frederick Swann
- Gloria Swanson
- Lee Sweatt
- Lalita Tademy
- Christopher Tanev
- Charles Thom
- Emmett Till
- Joe Tinker
- Tintin in America
- Joe Tipton
- Tonight, Tonight (The Smashing Pumpkins song)
- Torpedo...Los!
- Transformers: Dark of the Moon
- Lennie Tristano
- Tucker: The Man and His Dream
- Evan Turner
- Tyler Ulis
- Jim Umbricht
- Union Stock Yards
- United States Zouave Cadets
- 2020 University of Illinois Hospital strikes
- Up! Live in Chicago
- Harold Urey
- Juan Uribe
- Brian Urlacher
- Kirk Urso
- Jack Vainisi
- Virgin Hotels Chicago
- Dwyane Wade
- Wanted (2008 film)
- Genoa Washington
- Washington Heights, Chicago
- Washington Park (community area), Chicago
- Washington Park (Chicago park)
- Washington Park Court District
- Washington Park Race Track
- Washington Park Subdivision
- Washington Square Park (Chicago)
- Watch Dogs (video game)
- Alvin M. Weinberg
- Agnes Weinrich
- Tom Weisner
- Matthew West
- WGBO-DT
- When Harry Met Sally...
- Eli Whiteside
- Hoyt Wilhelm
- William W. Powers State Recreation Area
- Kenny Williams (basketball, born 1972)
- Ned Williamson
- Hack Wilson
- Chet Winters
- Al Wistert
- Whitey Wistert
- Greg Wohlwend
- Wolf Point, Chicago
- Wilbur Wood
- Leona Woods
- Al Worthington
- WrestleMania 2
- Wrigley Square
- Early Wynn
- Hoylande Young
- Voltairine de Cleyre
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File:20070616 Chris Young visits Wrigley (4)-edit3.jpg- File:20090524 Buildings along Chicago River line the south border of the Near North Side and Streeterville and the north border of Chicago Loop, Lakeshore East and Illinois Center.jpg
- File:Abbey Lincoln in 1966.jpg
- File:Amanda Berry Smith by T. B. Latchmore.jpg
- File:Apollo 17 Cernan on moon.jpg
- File:Barack Obama family portrait 2011.jpg
- File:Barack Obama with artistic gymnastic McKayla Maroney 2.jpg
- File:Bessie Coleman in 1923.jpg
- File:Big White Fog.jpg
- File:CTA Night.jpg
- File:CTA loop junction.jpg
- File:CTA red line rerouted.jpg
- File:Calle E Monroe St, Chicago, Illinois, Estados Unidos, 2012-10-20, DD 04.jpg
- File:Cardiss Collins - Restoration.jpg
- File:Charles Henry Turner at Sumner High School, St. Louis, Mo. Aug. 9, 1921.jpg
- File:CharltonHestonCivilRightsMarch1963Retouched.jpg
- File:Chicago Grant Park night pano.jpg
- File:Chicago Skyline Hi-Res.jpg
- File:Chicago Theatre blend.jpg
- File:Chicago and Northwestern railroad locomotive shop fsac.1a34676u.jpg
- File:Chicago sunrise 1.jpg
- File:Chicago top down view.png
- File:Chicago world's fair, a century of progress, expo poster, 1933, 2.jpg
- File:Composer Florence Price (cropped).jpg
- File:Democratic presidential ticket 1864b.jpg
- File:Dewey Defeats Truman.jpg
- File:Ed Walsh portrait 1911.jpg
- File:EdwardTeller1958 fewer smudges.jpg
- File:Enrico Fermi 1943-49.jpg
- File:Ernest Hemingway in Milan 1918 retouched 3.jpg
- File:GAGE, Lyman J-Treasury (BEP engraved portrait).jpg
- File:Grant Park, Chicago, Illinois, Estados Unidos, 2012-10-20, DD 03.jpg
- File:Grant Wood - American Gothic - Google Art Project.jpg
- File:Great presidential puzzle2.jpg
- File:IIT Machinery Hall.jpg
- File:James D Watson.jpg
- File:Jane Addams - Bain News Service.jpg
- File:Jane M. Byrne Interchange Traffic.webm
- File:Jesse Jackson, half-length portrait of Jackson seated at a table, July 1, 1983 edit.jpg
- File:Johnny Evers 1910 FINAL2sh.jpg
- File:Kurt Vonnegut by Bernard Gotfryd (1965).jpg
- File:Livestock chicago 1947.jpg
- File:Locomotives-Roundhouse2.jpg
- File:Luis Alvarez with a magnetic monopole detector - Restoration.jpg
- File:Mae Carol Jemison.jpg
- File:Margaret D. Foster, in Lab, 4 October 1919.jpg
- File:Marina City, Chicago, Illinois, Estados Unidos, 2012-10-20, DD 01.jpg
- File:Mary Garrity - Ida B. Wells-Barnett - Google Art Project - restoration crop.jpg
- File:Mest performing at Saint Andrew's Hall, Detroit, 2023-09-14 03.jpg
- File:Michelle Obama 2013 official portrait.jpg
- File:Muhammad Ali NYWTS.jpg
- File:Nighthawks by Edward Hopper 1942.jpg
- File:Official Portrait of President Reagan 1981.jpg
- File:Robinhunicke at thatgamecompany photoshoot, August 2009.jpg
- File:Ronald Reagan with cowboy hat 12-0071M edit.jpg
- File:Rosa Raisa (1917) - Archivio Storico Ricordi FOTO002701 - Restoration.jpg
- File:Samuel Reshevsky versus the World.JPG
- File:Shoeless Joe Jackson by Conlon, 1913.jpeg
- File:Stefan Heym (1982).jpg
- File:Tuskegee airman2.jpg
- File:Voltairine de Cleyre (Age 35).jpg
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1880 Greenback National Convention
