Road trip on Route 66 to Chicago, Illinois

Route 66 Road Trip to Chicago

When traveling westbound to California, Historic Route 66 begins in Chicago, Illinois
Historic Route 66 begins in Chicago, Illinois

The Mother Road in Illinois

Route 66 was one of the United States' first continuous stretches of paved highway, and served as a major path for those who migrated west.

"The Mother Road" was established on November 11, 1926, and ultimately stretched 2,448 miles from Chicago to Los Angeles.

The beginning point for a Route 66 road trip could be either Chicago or Los Angeles, depending on the direction of the trip. Most travelers seem to start their journey on Route 66 in Chicago, and head westbound, the direction taken by those leaving the Dust Bowl and those seeking a new life in the West. That is the direction we take on this website.

Chicago: The Route Begins

Illinois was the first of the eight states through which Route 66 passed to have its segment of U.S. 66 paved, at a time when much of the route across the country was still a gravel or dirt road. Illinois Route 66 took over Illinois State Highway 4, a pre-existing, fully paved two-lane road between Chicago and St. Louis.

Historic Route 66 spanned 301 miles in Illinois, traversing mostly level terrain.

The beginning point of Route 66 in Chicago has changed over the years. Today, the starting point is at East Adams Street (one way heading west) at South Michigan Avenue, and the end point is at East Jackson (heading east) at South Michigan. One way streets in the area can be difficult to navigate for first-time Route 66 visitors ... see area map below!

Map of downtown Chicago, Illinois showing the beginning point and ending point of Route 66


While in Chicago, many Route 66 travelers seek out Grant Park, the Willis Tower, Chicago Architecture River Cruise, Art Institute of Chicago, Museum of Science & Industry, the Magnificent Mile, Lincoln Park Zoo and the lakeshore shopping areas.

The ultimate Route 66 Chicago itinerary - 11/01/2023


Chicago ... the beginning point of Route 66 when heading westbound
Chicago, Illinois ... the beginning point of Route 66 when heading westbound

Lodging and Dining Options in Chicago

Chicago Travel and Vacation Guide at TripAdvisor

Chicago Travel Guide at TripAdvisor

View Chicago, Illinois, hotel listings and traveler reviews at TripAdvisor

Hotel listings and traveler reviews for Chicago

Restaurant reviews for Chicago

Attractions and things to do in Chicago

Chicago Route 66 reviews, photos, walking tours, hotels


More travel and tourism information at

Popular Attractions Around Chicago

Art Institute
The Art Institute of Chicago
Chicago Riverwalk
Chicago Riverwalk
Science & Industry
Museum of Science and Industry in Chicago, Illinois
Cruises on the waterways of Chicago
Cruises on the waterways of Chicago
Cloud Gate - aka "The Bean"
Cloud Gate ... aka "The Bean" in Millennium Park in Chicago, Illinois

Navy Pier
The Navy Pier in Chicago
Shedd Aquarium
Shedd Aquarium in Chicago
Field Museum
The Field Museum in Chicago

A popular stop for Route 66 travelers, at 565 West Jackson Boulevard in Chicago ... Lou Mitchell's website
Lou Mitchell's in Chicago ... a popular stop for those heading westbound on Route 66

Interactive Map of Chicago, Illinois

Route 66 Highlights After Leaving Chicago

Illinois travel map from the Gulf Oil Company

Once outside the metropolitan Chicago area, Route 66 followed the Pontiac Trail, a former Indian trail and stagecoach road.

From its beginning in Chicago, Route 66 headed southwest to Romeoville, Joliet, Wilmington, Dwight, Odell, Pontiac, Bloomington, Atlanta, Lincoln and Springfield. The segment from Chicago to Springfield is roughly a 2.5 hour drive.

Leaving Chicago and arriving in Joliet, travelers like to visit the Joliet Museum, Rialto Square Theatre and the Jacob Henry Mansion. The City of Dwight features a restored Ambler-Becker Texas service station as well as a wealth of historic structures. Odell, just down the route, is the locale of another restored gas station.

Pontiac is a great stopover traveling down Illinois, with the always popular Route 66 Hall of Fame a "must see" attraction. Other attractions include the Pontiac-Oakland Auto Museum and the Livingston County War Museum. Lincoln is home to the Postville Courthouse that Abraham Lincoln practiced law in, the world's largest covered wagon, The Mill Museum on Route 66, a telephone booth on top of the town hall, Lincoln College, and the Lincoln Heritage Museum.

Springfield was the hometown of U.S. President Abraham Lincoln. Visitors can tour the house where he lived, Lincoln Tomb State Historical Site, the Lincoln Presidential Library & Museum, and the Illinois State Capitol Building.

Leaving Springfield, Route 66 traversed Litchfield, Staunton and Hamel, and then continued on to the Chain of Rocks Bridge at St. Louis, where it turned west through Rolla, Springfield, Joplin and into Kansas and Oklahoma.

We've driven much of Route 66 in all eight states, including segments in Illinois. On this website we present road trips including original photographs, travel experiences and personal commentary.

Now let's head west on The Mother Road, where we will make stops at these 28 locations on Route 66 in Illinois starting in Chicago and ending at Granite City near St. Louis:

Chicago Atlanta
Romeoville Lincoln
Joliet Williamsville
Wilmington Springfield
Braidwood Auburn
Gardner Virden
Dwight Nilwood
Odell Litchfield
Pontiac Mt. Olive
Chenoa Staunton
Lexington Livingston
Towanda Hamel
Normal Edwardsville
Bloomington Collinsville
McLean Granite City


Illinois, Land of Lincoln ... Where the Road Begins
Illinois, the Land of Lincoln ...Where the Road Begins

Read more about the Route 66 license program at


Map showing the approximate route of U.S. Highway 66 from Chicago to St. Louis, Missouri
Alignments varied over time
Click the map for current routing information
Map showing approximate Route 66 location from Chicago to St. Louis, Missouri

Guides & Displays Along Route 66 in Illinois

The Route 66 interpretive display at Ambler's in Dwight
Dwight, Illinois Route 66 Kiosk

Visitors can explore unique people, places, and stories through a series of interpretive displays placed along Illinois' Route 66.

The Illinois Route 66 Scenic Byway in partnership with the Federal Highway Administration, the Schmeeckle Reserve at the University of Wisconsin at Stevens Point, and Illinois Route 66 communities have developed and installed three types of interpretive displays:

  • Wayside Exhibits
  • Experience Hubs
  • Interpretive Statues

Each display is placed in a location that has Route 66 significance and explains that importance through various media forms. Read more about the displays at

The Illinois Route 66 Wayside exhibits can be found in 17 communities along the Mother Road. Each wayside is placed at a site with historic significance and tells the story of the site’s relationship to Route 66.

The interpretive stations use illustrations, pictures, and audio to explore each site.

Illinois Route 66 Passport Stations

Don’t forget to bring a notebook and a pencil to collect all of the Illinois Route 66 Passport Stamps!

When you discover a stamp on a Wayside Exhibit simply place a piece of paper over the rubbing station and use your pencil to collect a unique engraving. See sample location in the photos below ...

Illinois Route 66 Wayside Exhibit with Passport Station Passport Station on an Illinois Route 66 Wayside Exhibit

More Information about Illinois Route 66

Enjoy Illinois - Office of Tourism: Route 66

Route 66 Association of Illinois

Illinois Route 66 Scenic Byway

Illinois Route 66 Segments at NPS


Route 66 Road Trips in Illinois

Route 66 road trip to Chicago, Illinois Route 66 Road Trip to Joliet, Illinois Route 66 Road Trip to Pontiac, Illinois Route 66 Road Trip to Bloomington and Normal in Illinois
Dwight, Illinois along Route 66 Route 66 road trip to Springfield, Illinois Route 66 road trip to Litchfield, Illinois

Road Trip Travel Guides for Various States Along Route 66

Need help and ideas when planning your road trip on Route 66? Here are travel guides and reviews by state ...

Route 66 Road Trips in Illinois Route 66 in Missouri Route 66 in Kansas Route 66 Road Trips Across Oklahoma
Route 66 in Texas Route 66 Across New Mexico Route 66 Across Arizona Route 66 Across California