Tours – Walking & Driving – Route 66 – Chicago Architecture & History

Limited Time Special – Route 66 Walking Tour at 66% of the Normal Price! One-third off for groups of five or more.

NEW series of Walking Tours: Stroll 66 on the 6th!
A tour each month on the 6th on and around Route 66 in Chicagoland!

Click here to view or print our Tour Brochure (.pdf format)

Chicago Walking Tours – Our Specialty

2-hour tours cover about one mile. Route 66 tours normally follow a circular loop. Standard 2-hour tours are $18 per person. All tours are by reservation. Special rates are available for large groups. Times are normally available 7 days per week, morning through evening hours. To reserve a tour or for questions, email dave@windycityroadwarrior.com or call 312-432-1284.

Limited Time Special – Route 66 Walking Tour at 66% of the Normal Price! One-third off for groups of five or more–only $12 per person! Groups of four are $15 per person!

Custom Driving Tours

Excursions around Chicago from 2 hours to a full day. Click Here for Details

Step-on Guide Service for Bus Groups

Let Windy City Road Warrior be your narrator for your bus or motor coach tours of the greater Chicagoland region. Click Here for Details

About Windy City Road Warrior

Your Windy City Road Warrior tour guide, Dave Clark, has been guiding tours in Chicago since 2005. He is a member of the Chicago Tour-Guide Professionals Association.





Chicago Route 66 Shield


Route 66 Loop Walking Tours

  • Get Your Kicks on Chicago’s Route 66 – Where the Mother Road Begins!
  • A Walk Through History on the First Mile of the Main Street of America
Begin Historic Route 66


The history of Route 66 in Chicago’s Loop is best understood when you park your car and put shoe leather on the sidewalks. The Route 66 corridor comes alive when you savor the sights and sounds, venture into the buildings that line the highway, and take a close look at the things that fly by your car window too fast.

Route 66 in Chicago’s Loop ran along Jackson Boulevard and Adams Street, parallel thoroughfares packed with historic sites and structures.

Route 66 Tour Highlight Map

Route 66 Tour Highlight Map -- Click Above for larger view


Route 66 East Loop Tour
We explore Route 66 on Jackson Boulevard and Adams Street Between Michigan Avenue and LaSalle Street.

  • See Chicago’s Historic Route Center, where Route 66 Began.
  • See buildings designed by Chicago’s famous architects.
  • See how Chicago’s railroad history shaped the Route 66 corridor.

Route 66 West Loop Tour
We explore Route 66 on Jackson Boulevard and Adams Street between LaSalle and Clinton Streets.

  • See the Chicago River Bridges that carried Route 66 traffic to and from the Loop.
  • See Union Station, Chicago’s last functioning passenger railroad station.
  • See Lou Mitchell’s Restaurant, where travelers have gathered since 1923.

Click here to view or print our Tour Brochure (.pdf format)

2-hour tours cover about one mile. Route 66 tours normally follow a circular loop. Standard 2-hour tours are $18 per person. All tours are by reservation. Special rates are available for large groups. Times are normally available 7 days per week, morning through evening hours. To reserve a tour or for questions, email dave@windycityroadwarrior.com or call 312-432-1284.

Limited Time Special – Route 66 Walking Tour at 66% of the Normal Price! One-third off for groups of five or more–only $12 per person! Groups of four are $15 per person!

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Custom Chicago Walking Tours

  • Choose your topic or theme–City Highlights – Architecture – History – Culture
  • Start where you want
  • Start when you want
  • Personal tours at public tour prices!

Lion Statue sculpted by Edward Kemys, Art Institute of Chicago

Lion Statue sculpted by Edward Kemys, Art Institute of Chicago


Windy City Road Warrior tours can arrange a tour of any area of Chicago by foot. We will take you on a walk through Chicago History, Architecture, and Culture–all at your convenience!

Here are some of our recent tours, all designed at the special request of our customers:

  • Walking Tour from the Tribune Tower to Millennium Park, highlighting the Burnham Plan of Chicago.
  • Architecture Tour of Louis Sullivan and Frank Lloyd Wright buildings in Chicago’s Loop.
  • Walking Tour of the sites of Chicago’s passenger railroad stations.

Click here to view or print our Tour Brochure (.pdf format)

2-hour tours cover about one mile. Standard 2-hour tours are $18 per person. All tours are by reservation. Times are normally available 7 days per week, morning through evening hours. Group rates are available. To reserve a tour or for questions, email dave@windycityroadwarrior.com or call 312-432-1284.

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Chicago Area Custom Driving Tours

Recent Driving Tour through Plainfield, IL, where 2 famous highways share pavement.

Recent Driving Tour through Plainfield, IL, where 2 famous highways share pavement.

If your interests include a desire to tour Chicago and the surrounding region by car, Windy City Road Warrior can provide narration and direction in your car or ours. Here are some examples of recent driving tours:

  • Driving tour of Chicago movie theaters and studios, from the location of the Essanay Studios, the the Biograph and Chicago Theaters, and more.
  • Driving tour of Route 66 from Chicago to Del Rhea’s Chicken Basket in Willowbrook
  • Personal tour by car encompassing visits to canal and history sites in Lockport, and Lemont, and Chicago sites of the city’s passenger railroad stations.

Times are normally available 7 days per week, morning through evening hours. Driving tours have a minimum fee of $50 and total cost varies by time, distance, and tour details. To reserve a tour or for questions, email dave@windycityroadwarrior.com or call 312-432-1284.

Click here to view or print our Tour Brochure (.pdf format)

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Step-On Tour Guide Service

Windy City Road Warrior Dave Clark Guiding a Bus Tour

Windy City Road Warrior Dave Clark Guiding a Bus Tour

If your organization is planning a motor-coach tour anywhere in the greater Chicago region, we can enhance your experience with knowledgeable narration of the history and lore of the area during the trip. Some recent step-on guide services have included:

  • A Route 66 tour from the Elmhurst Art Museum to the beginning of the highway in Chicago, with narration through Willowbrook, Burr Ridge, Indian Head Park, Countryside, McCook, Lyons, Berwyn, and Cicero.
  • A Frank Lloyd Wright architectural tour, encompassing a drive to the SC Johnson headquarters in Racine, Wisconsin, a drive-by of Wright-designed homes in Riverside, Illinois, and a visit to Wright’s Robie House on the University of Chicago campus.
  • A Chicago History and River tour, featuring a motor-coach ride from Rosemont, Illinois to Chicago’s Loop with narration of history related to the Chicago Fire, the Haymarket riots, and the city’s railroads; followed by narration of a tour along the Chicago River and the harbor in Lake Michigan.

Windy City Road Warrior provides step-on guide services, and we can recommend destination management companies (DMCs) that can provide a coach and driver. We can also work with any DMC you may already have retained. Times are normally available 7 days per week, morning through evening hours. The cost of guide services varies by length of the tour and requested destinations. To reserve a tour or for questions, email dave@windycityroadwarrior.com or call 312-432-1284.

Click here to view or print our Tour Brochure (.pdf format)

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