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

Windy City Road Warrior Tours

If your Roadie travel plans include a visit to Chicago, take advantage of my knowledge gained through years of research! Our 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 Motor Coach Tour Flier including current 2008 Schedule and Prices

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


Begin Route 66 sign in Chicago's Loop, near the historic Route Center.

"Get Your Kicks on Route 66" Motor Coach Tours

New for 2008! Windy City Road Warrior has partnered with Windy City Connection to bring you Route 66 from Chicago to Wilmington in the luxury of a modern Motor Coach!

After boarding the motor coach, we travel to Chicago’s “route center,” a crossroads that was the starting point of 66, as well as 9 Illinois state highways and 3 other US highways. The “route center” also served traffic for the Pontiac Trail, the Dixie Highway, and the Yellowstone Trail. We will enjoy a 1-hour walking tour in Chicago as we discuss the connection between the commerce of Chicago and the success of Route 66, which became the most traveled cross-state highway in Illinois.

The tour will follow Route 66 out of Chicago and through Cicero, Berwyn, Riverside, Lyons, McCook, Hodgkins, Countryside, Indian Head Park, and Burr Ridge. Along the way, Dave will discuss such historic sites as Douglas Park, the Castle Car Wash, Hawthorne Works, Henry’s Drive-In, Hofmann Tower, Stinson Airport, and the Wishing Well Motel. We will then enjoy lunch at historic Dell Rhea’s Chicken Basket in Willowbrook, Illinois.

Our lunch stop is at Dell Rhea's Chicken Basket on old 66 in Willowbrook

Following lunch, the tour will continue on Route 66 southwest through DuPage County and then south into Will County. We will get off the bus for a short walking tour of Downtown Joliet, including a view of the Rialto theater on the original alignment of Route 66 through town. We will walk past vintage buildings built of Joliet limestone and visit the Welcome Center and Gift Shop at the Joliet Historical Museum.

Guests re-board the coach and continue to Wilmington where there is time to enjoy shopping or perhaps take in a cool one at the local pub (previously a bank) before heading home on the most direct route.


Tour Inclusions:

In Joliet we visit the Joliet Historical Museum

  • Deluxe 55 Passenger Motor Coach
  • 10 Page Handout of Tour
  • 1 Hour Guided Walking Tour of Historic Buildings in Downtown Chicago
  • Lunch at historic Dell Rhea’s Chicken Basket including your choice of 3 entrees
  • Walking tour of Downtown Joliet
  • Visit to the Route 66 Welcome Center in Joliet
  • Free Time Shopping at Ben Franklin Store in Wilmington
  • Free Time Shopping in Downtown Wilmington


2008 Tour Dates:

The Gemini Giant at the Launching Pad Restaurant has greeted Route 66 travelers in Wilimington for 50 years.

The motor coach will depart from Woodfield Mall (except where noted) in Schaumburg unless the tour is exclusive for your group. In order to book this tour as an exclusive, you must have a minimum of 35 guests. The motor coach will pick you up at a pre-determined location convenient for your group. All tours operate on Saturday.

July 12, 2008July 26, 2008August 2, 2008
August 23, 2008 (Chicago Departure)September 6, 2008September 20, 2008
October 18, 2008October 25, 2008

Tour Times: 8:30 a.m. -- 5:30 p.m. (Chicago Departure 9:30 a.m. -- 5:00 p.m.)

Cost: $89.00 per person

Note: A minimum of 35 people is required to operate this tour. If the minimum is not met, a full refund will be issued.

Checks, Master Card and VISA accepted.

This tour is operated by:
Windy City Connection, Inc.
869 E. Schaumburg Road, Suite 163
Schaumburg, Illinois 60194

Please call Windy City Connection at 847-534-6550 to reserve your space.

Click here to view or print a Motor Coach Tour Flier including current 2008 Schedule and 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, arrangements can be made for me to accompany you in your vehicle to 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. Please note that I cannot provide a vehicle or a driver. 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.