Route 66 Through Illinois: Historic Stops from Chicago to the Mississippi

Route 66 begins in Illinois. From its eastern end in downtown Chicago, the highway ran roughly 300 miles southwest across the prairie through Joliet, Pontiac, Bloomington, Springfield, and Litchfield before crossing the Mississippi River into Missouri. The federal government approved the new numbered highway on November 11, 1926, so 2026 is the road's centennial year, and Illinois towns have spent it repainting signs, opening welcome centers, and celebrating the diners and gas stations that survived the interstate. This guide covers the most significant historic stops in order from Chicago to the river, with what each one is, why it matters, and whether it is open, closed, or changed as of late 2026.

1. A Short History of Route 66 in Illinois

Before it had a federal number, most of the Chicago-to-St. Louis road was Illinois State Route 4, already a paved, heavily used corridor. When federal and state highway officials laid out the national numbered system in 1926, the Chicago–Los Angeles route was at first assigned a different number. On April 30, 1926, Oklahoma highway promoter Cyrus Avery and Missouri officials meeting in Springfield, Missouri, telegraphed Washington proposing the number 66 instead, which is why Springfield, Missouri, calls itself the birthplace of Route 66. The system, including U.S. 66, was approved on November 11, 1926.

The Illinois route moved several times. The earliest alignment south of Springfield ran through Auburn, Carlinville, and Staunton; around 1930 the highway was shifted east to a straighter line through Litchfield and Mount Olive, stranding businesses on the old road. In Chicago, the starting point moved as streets were reconfigured. After World War II the road was steadily widened into a four-lane highway and then replaced by Interstate 55, and Route 66 was officially removed from Illinois in 1977. Brown "Historic Route 66" signs now mark the old alignments, and the corridor is the Illinois Route 66 Scenic Byway, a National Scenic Byway.

2. Chicago: Where the Road Begins

"Begin Route 66" Sign

Location: Adams Street just west of Michigan Avenue
Status: Standing; free photo stop

The original 1926 terminus was at Jackson Boulevard and Michigan Avenue, at the edge of Grant Park, and westbound traffic followed Jackson. Because Jackson and Adams later became one-way streets in opposite directions, the "Begin Route 66" sign stands on Adams, and the "End" sign for eastbound travelers is on Jackson. Traffic is heavy and parking is scarce, so most travelers take the photo on foot.

Lou Mitchell's Restaurant

Location: 565 W Jackson Blvd, Chicago
Status: Operating (breakfast and lunch; check hours)

William Mitchell opened his restaurant in 1923 and named it for his son Lou; according to the National Park Service, the first location was across the street, and the current building dates to 1949. It was listed in the National Register of Historic Places in 2006. Its long-running customs, free donut holes for people waiting in line and a small box of Milk Duds for women and children, have made it the traditional first breakfast of a westbound Route 66 trip. Weekend lines are common.

3. Joliet and Wilmington

Joliet Area Historical Museum and Route 66 Welcome Center

Location: 204 N Ottawa St, Joliet
Status: Open (check hours)

Joliet's history museum doubles as a Route 66 welcome center and a good place to pick up maps and current information on events along the northern section of the road. Two blocks away, the Rialto Square Theatre (102 N Chicago St), an ornate movie palace that opened in 1926, the same year the highway was numbered, still hosts concerts and shows.

Rich & Creamy

Location: 920 N Broadway St, Joliet (in Route 66 Park)
Status: Operating seasonally, typically spring through fall

This walk-up ice cream stand is known for the Blues Brothers figures on its roof, a nod to the 1980 film whose opening scenes were shot at the old Joliet prison nearby. It closes for the winter, so check before an off-season trip.

Gemini Giant

Location: South Island Park, Wilmington; Landing Pad shop at 110 S Park St
Status: On display at its new site; the Launching Pad restaurant is closed

The roughly 28-foot fiberglass astronaut holding a rocket was installed in 1965 to draw customers to the Launching Pad Drive-In, during the excitement of NASA's Gemini program. It belongs to the family of oversized fiberglass advertising figures collectors call "Muffler Men." The Launching Pad closed in 2022, and the statue and fixtures were auctioned in 2024; the buyer kept the Giant in Wilmington, and it was restored and moved less than a mile to South Island Park. A Route 66 souvenir shop called the Landing Pad opened near the statue in May 2025. If you have an older guidebook that sends you to 810 E Baltimore St, the Giant is no longer there.

4. Braidwood and Dwight

Polk-a-Dot Drive In

Location: 222 N Front St, Braidwood
Status: Operating

The Polk-a-Dot started in 1956 as a food stand in an old school bus painted with polka dots and later moved into a permanent building. Burgers, hot dogs, and shakes are served in a 1950s setting, with fiberglass figures of Elvis, Marilyn Monroe, James Dean, and the Blues Brothers outside. It was inducted into the Route 66 Association of Illinois Hall of Fame in 2002.

Ambler's Texaco Gas Station

Location: 417 W Waupansie St, Dwight (Old Route 66 at Illinois Route 17)
Status: Restored; visitor center owned by the Village of Dwight

Built in 1933 by Jack Schore, this small "house-style" station was run from 1938 to 1966 by Basil "Tubby" Ambler and sold gasoline under several brands until 1999, one of the longest runs of any station on Route 66. After it closed it was donated to the village, restored, and reopened in 2007 as a visitor center. Dwight's compact downtown, a short drive away, is worth a walk.

5. Pontiac

Illinois Route 66 Hall of Fame & Museum

Location: 110 W Howard St, Pontiac
Status: Open; free admission (hours vary by season)

Run by the Route 66 Association of Illinois, the museum occupies Pontiac's 1900 former firehouse; the collection had earlier been displayed in a hallway at the Dixie Truck Stop in McLean. Exhibits cover the road's businesses and people, including a tribute to Route 66 artist Bob Waldmire (1945–2009), son of the Cozy Dog's founder, whose painted vehicles became road icons. The association's Hall of Fame honors people and businesses, among them several stops in this guide.

Downtown Murals and the Pontiac-Oakland Museum

Location: Downtown Pontiac; museum at 205 N Mill St
Status: Murals visible year-round; museum hours vary, call ahead

Pontiac's downtown is covered with large outdoor murals, many painted by the Walldogs, a group of sign painters who work in the old hand-lettered advertising style, and the town's walkable square makes it one of the best overnight stops on the Illinois route. The Pontiac-Oakland Automobile Museum, which opened in 2011, displays cars and memorabilia from the Pontiac and Oakland brands.

6. Bloomington-Normal and Funks Grove

Steak 'n Shake's Birthplace

Gus Belt opened the first Steak 'n Shake in Normal in 1934, in a converted gas station on the highway. The original building is gone, but the chain's roots are part of the Bloomington-Normal Route 66 story, and the McLean County Museum of History in downtown Bloomington covers local history.

Funks Grove Pure Maple Sirup

Location: 5257 Old Route 66, Shirley
Status: Operating; shop open seasonally until the year's sirup sells out (usually by late summer)

The Funk family has been making maple sirup in this grove since Isaac and Cassandra Funk settled here in 1824, and Arthur Funk began selling it commercially in 1891. The family keeps the old spelling "sirup." Sap season usually ends by mid- to late March, and the shop stays open until the sirup runs out, which in most years is around the end of summer. Call ahead if you are making a special trip.

7. Springfield

Cozy Dog Drive In

Location: 2935 S 6th St, Springfield
Status: Operating, run by the third generation of the Waldmire family

Ed Waldmire's "Cozy Dog," a batter-dipped hot dog on a stick, became a Springfield institution after he opened the Cozy Dog Drive In in 1949. His son Buz ran the restaurant for decades, and the walls hold Route 66 memorabilia and tributes to the Waldmire family, including Buz's brother, the artist Bob Waldmire. In 2026 a 25-foot Cozy Dog sculpture was added to the Illinois Route 66 Experience at the state fairgrounds.

Shea's Gas Station Museum

Location: 2075 N Peoria Rd, Springfield
Status: Reopened in 2024

Bill Shea ran a gas station on Peoria Road for decades and filled it with oil-company signs, pumps, and memorabilia, turning it into one of the best-loved stops on the road. The museum closed after his death in 2013, and the collection was sold in 2015, but the city of Springfield revived the site, which held a grand reopening on May 20, 2024. Check current hours before visiting.

Maldaner's Restaurant and the Route 66 Twin Drive-In

Location: Maldaner's, 222 S 6th St; drive-in, 1700 Recreation Dr
Status: Both operating (drive-in is seasonal)

Maldaner's traces its start to 1884 and is regarded as Springfield's oldest restaurant; it sits downtown on the city's Sixth Street Route 66 corridor, a few blocks from the Lincoln Home National Historic Site and the Old State Capitol. The Route 66 Twin Drive-In, at Knight's Action Park, is a reopened older drive-in (the former Green Meadows) that takes its name from the highway, although it is not on a historic alignment.

8. Auburn, Litchfield, and Staunton

Auburn Brick Road

Location: Snell Road and Curran Road, north of Auburn
Status: Drivable public road

On the 1926–1930 alignment between Springfield and Auburn, about a mile and a half of road is still surfaced with red brick, laid in the early 1930s when this stretch was Illinois Route 4. It was listed in the National Register of Historic Places in 1998, chiefly for its engineering history. Drive slowly; it is a narrow rural road, and residents live along it.

Ariston Cafe

Location: 413 Old Route 66, Litchfield
Status: Operating

Greek immigrant Pete Adam started the Ariston in Carlinville in 1924. When the highway moved east, the business followed it to Litchfield, and the present building opened on July 5, 1935. The Adam family ran it until 2018, when new owners bought it and kept its name and traditions. It was listed in the National Register in 2006 and promotes itself as the oldest continuously operating restaurant on Route 66.

Sky View Drive-In

Location: 1500 N Historic Old Route 66, Litchfield
Status: Operating seasonally

Opened in 1950 or 1951 (sources differ), the Sky View is described as the last original drive-in theater still operating on Route 66 in Illinois. Check the season schedule; showings start at dusk.

Henry's Rabbit Ranch

Location: Staunton
Status: Closed to visitors after the founder's death; reopening uncertain

Rich Henry's roadside stop, with its vintage Volkswagen Rabbits, live rabbits, and Route 66 memorabilia, was one of the friendliest stops on the road. After Henry's death the ranch closed to visitors and the property was put up for sale; new local owners have announced plans to reopen it, but confirm before you go.

9. Collinsville and the Mississippi River

Brooks Catsup Bottle Water Tower

Location: 800 S Morrison Ave, Collinsville
Status: Standing; viewable from the street

Completed in 1949 by the W.E. Caldwell Company as a 100,000-gallon water tower for the G.S. Suppiger Company's Brooks catsup plant, the bottle-shaped tank sits on a tall steel base for a total height of about 170 feet. When the property was put up for sale in the early 1990s, local volunteers formed the Catsup Bottle Preservation Group and raised money to restore it, and the tower was listed in the National Register in 2002. It is on a side road from the main later alignment, so plan a short detour.

Old Chain of Rocks Bridge

Location: Illinois end reached from Illinois Route 3 via Chain of Rocks Road, near Madison/Granite City
Status: Open to pedestrians and cyclists

Opened in 1929 as a toll bridge, the mile-long Chain of Rocks Bridge carried Route 66 traffic across the Mississippi for decades. It is famous for a bend of about 22 degrees near the middle, built so river traffic could pass the city of St. Louis's water intake towers safely. Vehicle traffic moved to the new Interstate 270 bridge in 1967, the old bridge closed to cars in 1970, and after years of abandonment it reopened on June 19, 1999, as a walking and biking path, an effort led by the nonprofit Trailnet. Walk out to the bend for views of the intake towers and the river.

10. Planning the Drive

• Time: The drive itself takes most of a day, but two to three days lets you stop properly. A common split is Chicago to Pontiac, Pontiac to Springfield, and Springfield to the Chain of Rocks Bridge.
• Navigation: Follow the brown "Historic Route 66" signs, but expect to lose them at times. Jerry McClanahan's EZ66 Guide for Travelers gives turn-by-turn directions, and the Illinois Route 66 Scenic Byway publishes maps and event listings.
• Seasons: Ice cream stands and drive-in theaters are seasonal, and many small museums cut their hours in winter. Late spring and early fall are the best balance of open businesses and smaller crowds.
• Lodging: Very few original Route 66 motels survive in Illinois. Pontiac, Springfield, and Litchfield are convenient overnight bases with chain hotels and some independent inns.

Tips for Driving Illinois Route 66

• Call ahead. Family businesses change hours, close for vacations, or change hands. Every status in this guide was checked in late 2026, but confirm before a long detour.
• Pick an alignment. South of Springfield, the 1926–1930 route (Auburn, Carlinville) and the later route (Litchfield, Mount Olive) are different roads; decide which stops you want first.
• Stop at welcome centers. Joliet, Pontiac, Dwight, and Springfield all have Route 66 visitor information with current event calendars.
• Look up the markers. Many stops have historical markers; the free Historical Marker Database (hmdb.org) has their texts if you want the history before you arrive.
• Visit the local historical society. County societies along the route often hold photos of vanished motels and gas stations; find them in our Illinois historical societies directory.

Frequently Asked Questions

Where does Route 66 start in Illinois?

Route 66 starts in downtown Chicago near Grant Park. The original 1926 terminus was at Jackson Boulevard and Michigan Avenue, and the "Begin Route 66" sign stands on Adams Street just west of Michigan Avenue.

How long is Route 66 in Illinois?

About 300 miles, from Chicago to the Mississippi River at St. Louis, depending on which alignment you follow. Plan two to three days to see the major stops.

Is the Gemini Giant still in Wilmington?

Yes. After the Launching Pad restaurant closed and the statue was auctioned in 2024, the Gemini Giant stayed in Wilmington and was moved to South Island Park, where the Landing Pad souvenir shop opened nearby in May 2025.

Can you still cross the Chain of Rocks Bridge?

Yes, on foot or by bicycle. The Old Chain of Rocks Bridge closed to cars in 1970 and reopened in 1999 as a walking and biking path across the Mississippi, with access from the Illinois side via Chain of Rocks Road.

Why is 2026 a big year for Route 66?

The U.S. numbered highway system, including Route 66, was approved on November 11, 1926, so 2026 marks the road's 100th anniversary. Towns along the Illinois route have held centennial events throughout the year.