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- $26.95Chicago, Illinois: A Photographic PortraitAmazon
- $15.95Chicago Illinois Museum Of Science & Industry Souvenir PlateEtsy
- $38.99Chicago Illinois Central Train Vintage Advertisement Artehouse LLCWayfair
- $85.00Chicago Illinois State Souvenir Plate Museum Of Science & Industry U505 Submarine CollectibleEtsy
- $12.99Chicago Illinois Hockey Hawk Mascot Photo Patch Parody Embroidered Iron On Ab4Etsy
- $18.89Chicago Illinois State Street USA 1890 Vintage Victorian Rotogravure Photo Illustration For Framing Black & WhiteEtsy
- $129.99iCanvas "Chicago Illinois Skyline Red Beige" by Michael TompsettBed Bath & Beyond
- $129.99iCanvas "Chicago Illinois Skyline Rainbow" by Michael TompsettBed Bath & Beyond
- $22.99Delmo Chicago, Illinois Skyline by Sean PavoneWayfair
- $17.00Ditto Cleanser Can Advertising Tin Chicago IllinoisEtsy
- $8.00Fantastic Antique Early 1900 Sunset Postcard To Chicago, IllinoisEtsy
- $2.79Linen Postcard, Soldiers Field, Chicago, Illinois, Chicago Bears StadiumEtsy
- $19.99sterling Robbins Chicago Illinois Cityscape Souvenir Spoon Riverside 4 1/8"Etsy
- $3,600.001840's American Portraits, Oil Paintings, Husband & Wife, Chicago, IllinoisEtsy
- $25.99and upStallions Jazz Club Retro Abstract Horse Chicago Illinois By Daphne PolselliWayfair & 1 more
- $90.74and upStupell Stallions Jazz Club Retro Abstract Horse Chicago Illinois Canvas Wall Art - OrangeBed Bath & Beyond & 1 more
- $82.49Scarce 1909 West Chicago Illinois Opera House & State Bank Cyan Photo PostcardEtsy
- $15.00Old 1940's Shannon Lumber Co. Hardware Nail Apron & Original - Chicago IllinoisEtsy
- $124.99iCanvas "1940s Downtown Skyline Michigan Avenue Chicago Illinois USA" by Vintage ImagesBed Bath & Beyond
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- $100.00Vintage Monarch Cocoa Tin Lion Graphic Advertising Reid Murdock & Co Chicago Illinois CollectibleEtsy
- $34.00Antique Circa Late 1800S Blob Top Beer Bottle Schoenhofen Brewery Chicago Illinois Pre ProhibitionEtsy
- $45.001944 Ditto Direct Process Copy Fluid Gallon Can - Metal Old & Original Chicago, IllinoisEtsy
- $16.75Route 66 Map #1: Chicago, Illinois - St. Louis, Missouri (329 Miles) (Bicycle Route 66, 1)Amazon
- $10.00First Day Issue Stamp Boy Scouts 75Th Anniversary Oct 7Th 1985 Chicago IllinoisEtsy
- $12.00Chicago World Fair Map, World Fair Exposition Vintage Map Of Chicago, Illinois Expo, 1893Etsy
- $164.99Early 1900's Independent Brewing Association Rienzi Prima Beer Brewery Advertising Factory Postcard - Chicago, IllinoisEtsy
- $10.001953 Picture Pies Cook Booklet By Armour & Co, Chicago, Illinois 5.5x8.5 Free ShEtsy
- $32.00Vintage Matchbooks, Tower Club, Chicago, Illinois, Lot Of 2, Missing 3 Match Sticks, Free Ship in UsaEtsy
- $8.00C1930S Paulson Service Henry & Co. Chicago, Illinois, Jewelry Watch Makers, Antique Small Advertising Tin, Country Kitchen DecorEtsy
- $28.00Vintage Matchbook, Henricis Restaurant, Chicago, Illinois, Front Strike, Horse & Carriage, Missing 2 Match Sticks, Free Ship in UsaEtsy
- $8.00Cool Antique Vintage Colorized Linen Postcard Of Alexander Mckinlock Memorial Campus, Northwestern University, Chicago, Illinois 1945Etsy
- $30.00Vintage Matchbook, Pirates Landing, Restaurant, Bar, Midway Airport Chicago, Illinois, with 20 Match Sticks, Free Ship in UsaEtsy
- $30.00Vintage Matchbook, Park Avenue Cafe, Walton Place, Chicago, Illinois, Nyc, with 20 Match Sticks, Free Ship in UsaEtsy
- $10.001941 When Cars Need Room Pave With Concrete Portland Cement Association Chicago, Illinois, Vintage Highway Road Travel BrochureEtsy
- $103.99iCanvas "1950s Skyline Of Michigan Avenue Buildings And Chicago River Lift Bridge Chicago Illinois USA" by Vintage ImagesBed Bath & Beyond
- $84.00Vintage Early 20Th Century Banthrico Kalifornie Building & Loan Ass'n. Chicago Illinois "Time Flies" Antique Advertisement Coin Book BankEtsy
- $30.00Vintage Matchbook, George Diamond, Steak House, Wabash, Chicago, Illinois, Front Strike, with 30 Match Sticks, Free Ship in UsaEtsy
- $489.00Original Cities Photography by Robert Wojtowicz | Fine Art Art on Paper | EL TRAIN CHICAGO ILLINOIS - Limited Edition of 55Saatchi Art
- $65.99High Angle View of Spectators in a Stadium, Wrigley Field, Chicago Cubs, Chicago, Illinois, USA by Panoramic Images - Gallery-Wrapped Canvas Giclée PrWayfair
- $8.00Cool Old Antique Real Photo Postcard Rppc Of The Chicago Historical Society Building At Clark Street & North Avenue in Chicago, IllinoisEtsy
- $489.00Original Cities Photography by Robert Wojtowicz | Fine Art Art on Paper | CHICAGO RIVER AND EAST WACKER DRIVE CHICAGO ARCHITECTURE CHICAGO ILLINOIS -Saatchi Art
- $489.00Original Cities Photography by Robert Wojtowicz | Fine Art Art on Paper | LINCOLN PARK HOTEL LINCOLN PARK CHICAGO ILLINOIS BLACK AND WHITE - Limited ESaatchi Art
- $489.00Original Cities Photography by Robert Wojtowicz | Fine Art Art on Paper | FROZEN ICY CHICAGO RIVER WINTER DAY HEAVY SNOWFALL CHICAGO ILLINOIS BLACK ANSaatchi Art
- $489.00Original Cities Photography by Robert Wojtowicz | Fine Art Art on Paper | CHICAGO EL CHICAGO ELEVATED TRAIN CHICAGO ILLINOIS BLACK AND WHITE - LimitedSaatchi Art