Road Tripping Route 66: Chicago to St. Louis

A Route 66 Chicago-to-St. Louis road trip

This guide covers the first section from east to west, going from the start of Route 66 in Chicago to St. Louis. This section covers roughly 325 miles and would take about five hours to drive from point to point — though doing it in one day would defeat the purpose of a leisurely road trip. The best places to stop along the way range from sprawling museums to quirky roadside attractions.

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Sections:

• Chicago
• Joliet, Illinois
• Pontiac, Illinois
• Springfield, Illinois
• Litchfield, Illinois
• St. Louis

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Chicago: The official start of Route 66

The intersection of Adams Street and Michigan Avenue in downtown Chicago, just south of Millennium Park, is Route 66’s historic starting point. A brown-and-white “Begin Route 66” sign marks the spot near the Art Institute of Chicago. When the highway was established in 1926, Chicago was already an industrial and manufacturing powerhouse, making it a natural starting point for a cross-country route designed to speed up commerce.

Spend your first day exploring Chicago on foot. Walk the Chicago Riverwalk to understand how trade shaped the city long before automobiles did, or check out the Chicago History Museum for exhibits on everything from the Great Chicago Fire to how railroads shaped the city (and country). Spend the night in the Loop, Chicago’s central business district, so you can park the car and explore downtown on foot and by train..

Joliet, Illinois: Architecture, theater, and canalside trails

Chicago to Joliet drive time: 46 miles/55 minutes

Though it’s only about an hour from Chicago, travelers with plenty of time to explore may want to stay for a night in Joliet. The Old Joliet Prison, built in 1858, has guided tours through cellblocks and yards that held inmates for more than a century. It’s a huge facility and offers everything from architecture and artifact tours, to after dark tours and tours told from a historical inmate perspective. Tours are bookable online and last about 90 minutes.

Downtown, Joliet’s Rialto Square Theatre opened in 1926 (the same year as Route 66) and often hosts concerts and touring Broadway shows. Thanks to the ornate restored interior, it feels a bit like stepping back in time. For daytime exploration, head to the Illinois Rock and Roll Museum on Route 66, rent bikes to pedal along the town’s miles of connected waterfront trails, or go on a guided hiking, birdwatching, or mushroom foraging session at sprawling Joliet Park.

On your way out of town, be sure to stop at the Gemini Giant for a photo op. It’s a 30-foot-tall fiberglass statue of an astronaut built in the 1960s, and it’s one of Route 66’s most photographed landmarks. It sits near the restored and renovated Launching Pad diner, making it an easy brunch or lunch stop. If you’re not hungry by the time you make it there, keep going to the vintage Polk-a-Dot Drive-In, which is decorated with statues of pop culture figures that show how early stops on Route 66 used photo ops and quirky decor to draw drivers off the road.

Pontiac, Illinois: Route 66 history, classic cars, and murals

Joliet to Pontiac drive time: 61 miles/1 hour

Before arriving in Pontiac, you’ll pass the Ambler-Becker Texaco Station in the town of Dwight. It was built in 1933 and now serves as a Route 66 visitor center. Nearby, you can still see preserved stretches of the original brick road. Past that in the town of Odell is the 1932 Standard Oil station, also offering vintage Americana vibes and is easy to find thanks to the massive “Route 66 Roadside Attraction” sign that stands out front.

In the town of Pontiac, don’t miss the packed Route 66 Association of Illinois Hall of Fame and Museum in a former fire station. It houses vintage signage, photographs, and memorabilia from the road’s long history, plus a gift shop and plenty of photo opportunities. If the history of the road is your thing (which it likely is, if you’re dedicating a road trip to it), next door is the Pontiac-Oakland Automobile Museum, filled with classic cars manufactured in Illinois.

If you want to stretch your legs before getting back in the car, follow the downtown mural walk, with more than 20 large-scale vintage-inspired pieces celebrating Route 66 and Illinois history.

Springfield, Illinois: Abe Lincoln and the Cozy Dog Drive-In

Pontiac to Springfield drive time: 105 miles/1 hour, 45 minutes

Springfield deserves a full day. The Lincoln Home National Historic Site preserves the only home Abraham Lincoln ever owned and has been restored to its 1860 appearance. It’s managed by the National Park Service and has free ranger-led tours every day that go inside the historic home. However, visitors can also walk around the four blocks surrounding his home, which have been restored to feel as if you’re back in the 1860s. The grounds, tours, and displays tell not just about the life of Lincoln, but about other noteworthy events of the time, including heroes of the Underground Railroad and the fight to end slavery in the US.

After exploring Lincoln’s former digs, a stop at the famous Cozy Dog Drive-In is essential. The Cozy Dog dates to 1946, and the Route 66 Drive-In followed in 1949. The interior is still filled with memorabilia from Route 66’s peak years.

Springfield has plenty of excellent hotels, but a standout option is the Inn at 835. It’s a boutique hotel decked out in a historic style similar to when it first started hosting travelers in the early 1900s. For a more modern option still rooted in history, you could also consider the luxury Bressmer Hotel, housed in a historic mansion now on the National Register of Historic Places.

Litchfield, Illinois: Dining and drive-in movies

Springfield to Litchfield drive time: 46 miles/50 minutes

As you enter Litchfield, stop for lunch at Ariston Cafe, which opened in its current site on Route 66 in 1935. It’s the oldest continually operating restaurant along the highway, and was added to the National Register of Historic Places in 2006.

In the early 1960s, there were more than 4,000 drive-ins across the US. Today, that number is down to about 300, with many operating only occasionally. But if you’re road tripping after April, you’ll have a chance to experience one of the most well-known in the country: the Sky View Drive-In, operating seasonally since 1950. It has a full concession bar and still retains the vintage feeling it did when it first began pulling in travelers heading south on Route 66.

Old Chain of Rocks Bridge

Litchfield to Old Chain of Rocks Bridge drive time: 53 miles/50 minutes

Before entering St. Louis, detour to the pedestrian- and bike-only Old Chain of Rocks Bridge. It was built in 1929 but became part of Route 66 in 1936. It’s one mile long with an unusual 30-degree bend at its midpoint. It’s one of the few original Route 66 bridges still accessible to the public and the views of the Mississippi River with the St. Louis skyline to the south are hard to beat. It’s free, photogenic, and it was used as a filming location for Escape from New York in 1980 — reason enough to stop.

If you’re a fan of crime history, stop at the nearby Luna Cafe, supposedly a favorite haunt of gangster Al Capone when he was driving down from Chicago. Today, it’s more of a dive bar, but it makes for a fun place to grab a beer.

St. Louis: Gateway to the West

Old Chain of Rocks Bridge to downtown St. Louis drive time: 15 miles/25 minutes

Like Chicago, St. Louis deserves a full day — ideally, at least two. Start with the obvious: the Gateway Arch. It’s taller and more impressive in person than any photo suggests, and the tram ride to the top (630 feet up) gives visitors sweeping views of the Mississippi River. It was designed by famous mid-century architect Eero Saarinen and is still the tallest man-made monument in the nation. The redesigned museum at its base is a fascinating place to learn about the good and bad parts of America’s westward expansion.

From there, head to the City Museum. It’s part playground, part art installation, and part architectural marvel, built almost entirely from materials reclaimed in St. Louis. It has caves, rooftop Ferris wheels, and a school bus hanging off the edge of the building. It may sound like a McDonald’s Play Place, but it’s adult friendly with 18-and-over evening events, too.

Once you work up an appetite climbing and jumping, head to Ted Drewes Frozen Custard. It’s a quintessential dessert stop opened in 1929 and known for its famous “concretes” — custards so thick you can turn it upside down. It’s always crowded but completely worth the wait.

History buffs should carve out time for the National Museum of Transportation, home to more than 190 major exhibits, including rail equipment, cars, aircraft, and Route 66 paraphrenalia. And if you’re into St. Louis brewing history (which predates Route 66 by decades), swing by the home of one of the most well-known breweries in the world: Anheuser-Busch. The sprawling brewery campus has tons of tours, ranging from production tours to beer pairing dinners and visits with the brand’s well-known Clydesdales.

You’ll find any kind of hotel you can imagine in St. Louis (as well as reasonably priced Airbnbs) but excellent options with a historic slant include the The Chase Park Plaza and the 21c Museum Hotel. The Plaza has been hosting well-to-do Route 66 travelers since the highway’s early days and still has an old-Hollywood sense of style, while the 21c Museum Hotel is housed in a former YMCA and doubles as a modern art museum.

Next up: (Part 2): Road tripping Route 66: St. Louis, Missouri, to Amarillo, Texas