Windy City Road Warrior - Books & More

Images of America: Route 66 in Chicago

Vintage photographs and postcard views, as well as contemporary images, are weaved together with narrative and captions to tell the pictorial history of the world's most famous highway and the city in which it began.

Much as Route 66 and the city of Chicago share a kindred history, so do the art and text, paired perfectly so that readers get plenty of information and are able to see what the author is talking about — Jon P. Callender, American Road Magazine.

David Clark has produced an excellent volume tracing the Route 66 corridor through the Chicago of today and back to early Native American trails and waterways…Clark is noted for his outstanding research and entertaining writing style and this book does not disappoint in either category— Bob Moore, Route 66 Magazine.

First place winner, nonfiction history book, 2008 Illinois Women's Press Association Communications Awards.

Softcover: 128 Pages, 6 1/2 inches wide x 9 3/16 inches tall, 195 photos & illustrations

Exploring Route 66 in Chicagoland

This is the only guidebook to concentrate on the place where the Mother Road begins.

  • Four chapters tell the biography of the thoroughfares that make up Route 66 in Cook County: Jackson Boulevard, Adams Street, Ogden Avenue, and Joliet Road.
  • Driving guide chapters show the Route with text keyed to strip maps that describe the current sights as well as the sites of historic structures now departed.
  • Self-guided walking tour of Route 66 through Chicago's Loop and West Loop.
  • Side trips, dining, attractions, and more!

Exploring Route 66 in Chicagoland is not just a guidebook of the Mother Road in Chicago, but a history primer of that great city…The book not only provides historical capsules of the buildings and places along Route 66, but also of the streets themselves–Ogden Avenue, Jackson Boulevard, Adams Street, and Joliet Road…Exploring Route 66 in Chicagoland made me re-appreciate the magnificence of the Windy City. — Ron Warnick, Route 66 News

Clark is a long recognized expert in the area of Route 66 in Chicago and has published articles in numerous publications, including Route 66 Magazine. But with Exploring Route 66 in Chicagoland, he has truly brought to the Roadies of the world the best researched and most detailed look at Chicago's Route 66 ever produced…Loaded with history, excellent contemporary and historic photographs, well thought out maps, and amazing detail, Exploring Route 66 in Chicagoland is a must have for anyone interested in exploring where Route 66 begins. — Bob Moore, Route 66 Magazine

Softcover: Comb Binding (lay flat), 150 Pages, 9 inches wide x 11.5 inches tall, 309 photos & illustrations, 31 driving and walking tour maps

The Roads that Lead to Lincoln: Finding Honest Abe on the Historic Highways of Illinois

From the Back Cover of The Roads that Lead to Lincoln:.

At the crossroads of the Dixie Highway and the Lincoln Highway in Chicago Heights, Illinois, there is a statue of Abraham Lincoln with the inscription, On the Road to Greatness. Lincoln's life before his move to Illinois was typical of frontier, hardscrabble existences in the early 19th century American West. His road to greatness truly began when he set out on his own at age 23, and his journey led him to champion the internal improvements of the natural landscape of Illinois. In his day, those improvements were the bridges, railroads, waterways, and connecting roads that would impose a civilization on the wild frontier. Thanks to his contributions, we can now explore the places where Lincoln practiced law, engaged in politics, and raised a family along the Historic Highways of Illinois.

This book traces the sites relating to Lincoln to be seen on three of the Illinois National Scenic Byways: Route 66, the Great River Road, and the Lincoln Highway. Along these thoroughfares, we follow in Lincoln's footsteps along his Roads to Greatness.

  • Chapter One: What have we done to Abe? A look at the cultural and commercial ways we have used Lincoln's name, his likeness, and his legend..
  • Chapter Two: Lincoln's Life in Illinois. A look at the years Lincoln lived in Illinois, from 1831 to 1861. His family, his law practice, and the politics of the day and his place within the larger story are all covered.
  • Chapter Three: Funeral Train. On the verge of a successful resolution to the tragic Civil War, Lincoln becomes one of the last martyrs to the cause of Union and human rights. A nation mourns and pays tribute.
  • Chapters Four-Six: A guide to the historic sites and monuments located on or near the Historic Highways of Illinois: Route 66, The Great River Road, and the Lincoln Highway.

Softcover: Comb Binding (lay flat), 80 Pages, 9 inches wide x 11.5 inches tall, 104 photos & illustrations, 3 maps

Chicago Route 66 Set of 7 Color Postcards

This set of seven full–color postcards of scenes from Route 66 show contemporary views along the Mother Road corridor in Chicago, where the road begins. The Begin Route 66 sign, Jackson Boulevard, Buckingham Fountain, Lou Mitchell's Restaurant, Route 66 in Berwyn IL, the Adams Street Bridge, and the Castle Gas Station (2 views) are featured.

  • Begin Route 66 Postcard — The Begin Historic Route 66 sign is located on Adams Street west of Michigan Avenue in Chicago's Loop.
  • Jackson Drive Skyline Postcard — This view looking west from the 1937–1977 starting point of Route 66 shows the two buildings that framed the original 1926–1937 starting point of the highway.
  • Buckingham Fountain Skyline Postcard — Buckingham Fountain has graced Chicago's Grant Park since 1927, and it was waiting there for Route 66 when the highway was extended east to Lake Shore Drive in 1937.
  • Lou Mitchell's Restaurant Postcard — Chicago's Jackson Boulevard has carried Route 66 traffic since 1926, but Lou Mitchell's Restaurant has been on the Boulevard since 1923.
  • Berwyn Postcard — Both photos on the front of the card show Ogden Avenue in Berwyn looking east at Home Avenue. Left: Circa 1900. Right: 2011 view.
  • Adams Street Bridge Postcard — The Adams Street Bridge has carried westbound Route 66 traffic over the Chicago River since 1953.
  • Castle Station Postcard — Both photos on the front of the card show the Castle Standard Oil Gas Station built in 1925 at 3801 W. Ogden Ave. in Chicago.

7 Color Postcards 5.5 inches by 4.25 inches packed in an archival acid-free polypropylene sleeve.

Postcards of America: Route 66 in Chicago

This set of fifteen black & white postcards are images culled from the book Images of America: Route 66 in Chicago

  • Michigan Boulevard — Circa 1921 image looking north toward the Route Center of Michigan and Jackson.
  • Ogden Boulevard — In 1907, Ogden Boulevard through Douglas Park was paved with grass parkways separating a center two-way driveway from one-way side drives.
  • Grant Park — 1930s aerial view of Grant Park, built on landfill on Chicago's lakefront.
  • Jackson and Michigan — 1916 view looking north from Chicago's Route Center intersection of Jackson and Michigan, which became the start of Route 66 in 1926.
  • Adams Street Bridge — Swing Bridge built in 1889 and replaced by current lift bridge in 1927. Adams was westbound Route 66 from 1953 to 1977.
  • Art Institute — 1917 view of the Art Institute, at Michigan and Adams. Northbound Michigan Avenue and westbound Adams Street became westbound Route 66 in 1953.
  • Illinois Central Depot — IC station is shown here post-1893 as it looked at the south end of Grant Park, looking south from Congress.
  • Douglas Park — Boaters on holiday in Douglas Park around 1915.
  • Cable Car — On State Street north of Adams Street, a cable car in the foreground pulls a horsecar and trolley car. Prior to 1905, overhead electric lines were banned from Chicago's Loop, so trolleys that ran on their own power in the neighborhoods had to hitch a ride with a cable car downtown.
  • Union Station — Union Station circa 1930. Jackson Boulevard is in the foreground and was Route 66 in 1926.
  • Ogden Avenue — 1933 photograph looking west on Ogden Avenue west of Pulaski Road. Buresch Motors, with cars lined up for service in front, was a Hudson Dealership at 4038 W. Ogden
  • Raklios — In the early decades of the 1900s, John Raklios was the Cafe King of Chicago, with two dozen restaurants in the downtown area. Four were on the original alignment of Route 66 and all were within two miles of the route.
  • Stratford Hotel — The Stratford was located at the southwest corner of Jackson and Michigan, the eventual Route Center start of Route 66.
  • Chicago Board of Trade Building — Chicago's tallest building when built at Jackson and LaSalle.
  • View from the Straus Building — 1929 view north from the Straus Building, located at the southwest corner of Jackson and Michigan.

15 Black & White Postcards 6 inches by 4.25 inches packed in an archival acid-free clear vinyl sleeve.

Route 66 Chicago - Walking Tours

Gift Certificate for Two People — Your choice of Route 66 Chicago Walking Tours — Take a Walk on the 66 Side:

Gift Certificate is transferable and does not expire. Delivered via email. To Redeem, contact InSites To Go at

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