• Geografie: Metropolregion Chicago – Cook County (Illinois)
• Stadtteile: Loop (Chicago) – Little Italy (Chicago)
• Gewässer: Michigansee – Chicago River – Illinois Waterway

• Straßen: Magnificent Mile
• Gebäude: 311 South Wacker Drive – 333 Wacker Drive – Aon Center – Home Insurance Building – John Hancock Center – Masonic Temple – Monadnock Building – Willis Tower – Trump International Hotel and Tower – Aqua – The Legacy at Millennium Park – Skybridge – Tribune Tower – Xerox Center – AT&T Corporate Center – Two Prudential Plaza – 900 North Michigan Building – Wrigley Building
• Parks:  Millennium Park - Grant Park
• Sehenswürdigkeiten: Cloud Gate - Crown Fountain - Buckingham-Brunnen - Petrillo Music Shell - Jay Pritzker Pavilion - Navy Pier - Nichols Bridgeway - BP Pedestrian Bridge - Lurie Garden
• Festivals: Chicago Blues Festival - Chicago Jazz Festival - Lollapalooza

• Unternehmen: Wm._Wrigley_Jr._Company – Sears – Skidmore, Owings and Merrill
• Medien: Chicago Sun-Times – Chicago Tribune – Polvision
• Finanzwelt: Chicago Mercantile Exchange - Chicago Board of Trade
• Bildung: University of Chicago - Northwestern University - University of Illinois at Chicago - Loyola University Chicago

• ÖPNV: Chicago Transit Authority – Chicago Elevated – Bahnhöfe in Chicago
• Eisenbahngesellschaften: Belt Railway of Chicago
• Ehemalige Eisenbahngesellschaften: Chicago and North Western Railway – Chicago Great Western Railroad – Chicago, Rock Island and Pacific Railroad – Chicago, Burlington and Quincy Railroad – Chicago, Milwaukee, St. Paul and Pacific Railroad – Illinois Central Railroad
• Flughäfen: Flughafen Chicago O'Hare – Flughafen Chicago-Midway – Meigs Field
• Individualverkehr: Interstate 57 – Interstate 55

• Geschichte: Großer Brand von Chicago – Haymarket Riot – World_Columbian_Exposition
• Liste der Söhne und Töchter von Chicago
• Persönlichkeiten: Johnny Torrio – Al Capone – Chicago Seven – Harold Washington – Barack Obama
• Liste der Bürgermeister von Chicago: Richard M. Daley – Richard J. Daley

• Kultur: The Second City
• Religion: Erzbistum Chicago – Chicago Temple - Marienmoschee
• Museen: Art Institute of Chicago – Museum of Contemporary Art – Museum of Science and Industry – Shedd Aquarium – Brookfield Zoo – Adler-Planetarium – Field Museum of Natural History
• Musik: Chicago Symphony Orchestra - AACM

• Musikrichtungen: Chicago-Jazz – Chicago Blues – Chicago House
• Clubs: Green Mill – The Jazz Showcase - Warehouse – 708 Club

• Sportclubs: Chicago Bears – Chicago Blackhawks – Chicago Bulls – Chicago Cubs – Chicago White Sox – Chicago Fire FC – Chicago Wolves
• Sportveranstaltungen: Chicago-Marathon
• Sportstätten: Comiskey Park - United Center – Soldier Field – Wrigley Field – Guaranteed Rate Field

Vereinigte Staaten

New York City

Los Angeles

Seattle

Galena and Chicago Union Railroad – Black Metropolis Historic District – Burnham Plan of Chicago – Central Manufacturing District - Bubbly Creek - Lager Beer Riot

Bauwerke: James R. Thompson Center – National Pythian Temple – Overton Hygienic Building – Chicago Bee Building – Chicago Defender Building – Wabash Avenue YMCA – Unity Hall – Supreme Life Building – Eighth Regiment Armory – Victory Monument – Harold Washington Library Center – Calumet National Bank Building – Fine Arts Building (Chicago) – S. A. Foster House and Stable – Page Brothers Building – Tivoli Theatre – Harris Theater – Palmolive Building - Stateway Gardens - Robert Taylor Homes - Flat Iron Building (Chicago) - Aragon Ballroom - Riviera Theatre - Uptown Theatre - Edgewater Beach Hotel - Riverside Plaza

Biografien: John G. Shedd – Merrill C. Meigs – Jean-Baptiste Pointe du Sable – Louis Grell – Edward J. Burling - Philip Danforth Armour - Gustavus Franklin Swift - Potter Palmer - Frederick P. Dinkelberg - Joachim G. Giaver - Edward Millman - John W. Norton - Edward Kemeys - Mike Royko

Parks: Lincoln Park – Garfield Park Conservatory – Jackson Park – Washington Park – Garfield Park – Avalon Park (Chicago) – Fuller Park – Gage Park – Humboldt Park

Unternehmen: Spiegel, Inc. - LaSalle Bank - Armour and Company - Goldblatt's - BMO Harris Bank - Container Corporation of America

Öffentliche Einrichtungen: Chicago History Museum – Chicago Public Library – Chicago Architecture Center - DuSable Museum of African American History - John H. Stroger Jr. Hospital of Cook County - National Museum of Mexican Art - Peggy Notebaert Nature Museum

Zeitungen: Chicago Bee – The Chicago Defender – The Prairie Farmer – Chicago Democrat

Veranstaltungen: Taste of Chicago

Verkehr: Galena and Chicago Union Railroad – Grand Central Station (Chicago) – Panama Limited - Dan Ryan Expressway - Stevenson Expressway - Kennedy Expressway - Metropolitan West Side Elevated Railroad - Division Street - Wells Street Bridge – mehr