Windy City Road Warrior Logo
HOME
UPCOMING EVENTS
GIFT SHOP
CONTACT ME
The 1924 SW Straus Building, with the 1972 CNA Center in the background
HOME
UPCOMING EVENTS
GIFT SHOP
CONTACT ME
The 1889 Monadnock Building, designed by John Root, stands at Jackson and Dearborn.
HOME
UPCOMING EVENTS
GIFT SHOP
CONTACT ME
The former headquarters of the Chicago, Burlington & Quincy Railroad, as seen from Canal Street
HOME
UPCOMING EVENTS
GIFT SHOP
CONTACT ME
An obelisk on Wacker Drive, with the west entrance of the Sears Tower in the background
HOME
UPCOMING EVENTS
GIFT SHOP
CONTACT ME
Lyons, Illinois' Hofmann Tower, built in 1908

Windy City Road Warrior Tours

If your Roadie travel plans include a visit to Chicago, Windy City Road Warrior guided tours can help interpret the shared history of Chicago, the highways, and the other forms of transportation used as the United States grew through the 19th and 20th centuries.

Click here to view or print a Walking Tour Brochure including current Prices


A view east from the Sears Tower Skydeck. The road running vertically in the image all the way to the Lake Michigan Shore is Jackson Boulevard, US 66. Westbound 66, Adams Street, is seen running vertically at the lower left edge of the image.

East Loop Walking Tour

The East Loop Walking Tour includes a discussion of why Jackson Boulevard was chosen to be the original route of US 66, and will include information about the historic buildings to be seen on Adams, Jackson, and Michigan Avenue between LaSalle Street and Lake Shore Drive.

Edward Kemys Lions Statues have graced the entry to the Art Institute of Chicago since 1893

Highlights include:

Architectural history of the Chicago Board of Trade, LaSalle Street Bank Buildings, John Root's Monadnock and Rookery Buildings, the Marquette Building, the Railway Exchange, and more...

A look at why there would be no route 66 if not for Chicago...

A look inside the lobbies and public spaces of the buildings, including an atrium designed by Frank Lloyd Wright (depending on building hours)...

History of U.S. Transportation, from the early explorers through the Waterways, the Railroads, and of course, the Highways...

Tours usually last about 2 hours and we travel about 1 mile, no stairs. Group and Individual Rates Available. Interested? Click Here to e-mail me, or Click Here for contact info!

Click here to view or print a Walking Tour Brochure including current Prices

Jackson Blvd Bridge over Chicago River, built 1915

West Loop Walking Tour

The West Loop Walking Tour includes information about the historic buildings to be seen on Adams and Jackson between LaSalle and Clinton Streets.

Union Station, built in 1924 at Jackson, Adams and Canal

Highlights include:

Architectural history of the Insurance Exchange, the Brooks Building, the former headquarters of the Chicago, Burlington & Quincy and the Chicago Northwestern Railroads, the Sears Tower, Union Station, and more...

A look at one of the oldest bridges still in use along Route 66...

A look inside the lobbies and public spaces of the buildings, including a post-modern Palm Court (depending on building hours)...

A visit to a place where the whole history of US transportation can be visualized, from the waterways, the railways, and of course, the highways...

Tours usually last about 2 hours and we travel about 1 mile, some stair-climbing. Group and Individual Rates Available. Interested? Click Here to e-mail me, or Click Here for contact info!

Click here to view or print a Walking Tour Brochure including current Prices

Castle Car Wash, built 1926 on Ogden Avenue in Chicago's North Lawndale Community Area

Narrated Driving Tours

If you would prefer to drive portions of Chciagoland's famous US Highways, including 66, 32/34, and 41, rather than walk, Windy City Road Warrior can provide narration concerning the sites and history.

Old St. Pat's on Adams Street, oldest church in Chicago, built in 1856

Highlights could include:

The oldest church still standing in Chicago, Greektown, and Chicago's former garment and warehouse district, all in the West Loop community area of Chicago...

A look at the gothic Cook County Hospital, inspiration for the TV show E.R., and a ride through the Tri-Taylor neighborhood, featuring unique architecture and a memorial to veterans of the Viet Nam war...

A ride through the Lawndale community area, home to the classic Castle Car Wash, stately greystone apartment buildings, and the industrial site that was once the Western Electric Hawthorne Works...

Henry's Hot Dogs in Cicero dates to the 1950s

A ride through the town of Cicero, home to Henry's Drive-in, and through Berwyn, where the suburban car culture still lives on 66...

A drive along both of the alignments of 66 through the village of Lyons, home of the landmark Hofmann Tower, with side trips to see remnants of the I&M Canal and bridge sites of the state highway that preceded 66, Illinois Route 4...

Rates will vary depending on the length of tour desired. Interested? Click Here to e-mail me, or Click Here for contact info!

© 2004 by David G. Clark. All rights reserved. No part of this website may be reproduced or transmitted in any form or by any means without the express written permission of the author/webmaster. All photos and graphics by David G. Clark unless otherwise credited. The contents of this website are believed to be correct at the time of posting. Nevertheless, the Author/Webmaster cannot accept responsibility for errors or omissions, or for changes in details provided here.