The Ultimate Route 66 Foodie Road Trip: Chicago to St. Louis
Darley Newman’s Must-Stop Restaurants Along the Mother Road
There’s no better way to experience Route 66 travel than through its food.
As Emmy Award-winning host of Travels with Darley, Darley Newman has traveled the world, but when it comes to classic American road trips, she knows that some of the most memorable experiences happen at roadside diners, historic cafes, and hidden local gems.
On her journey from Chicago to St. Louis along Route 66, Darley highlights the iconic restaurants, nostalgic eateries, and can’t-miss foodie stops that define this legendary highway.
If you’re planning a Route 66 road trip or searching for the best foodie destinations near Chicago, this guide maps out exactly where to eat—mile by mile.
Listen to the Route 66 Road Trip Podcasts, part 1 and 2, to plan your road trip using Darley Newman’s first-hand experiences driving from Chicago to St. Louis and stopping a lot along the way.
ILLINOIS → CHICAGO
Where Route 66 (and the Food Journey) Begins
The Palmer House Hilton
Famous for: The original brownie (invented here in the 19th century)
Why go: A historic, indulgent start to your Route 66 journey
“If you’ve worked up an appetite…dine on a delicious brownie where it was first created.”
Lou Mitchell’s
Since: 1923
Known for: Classic breakfast, coffee, eggs
Vibe: Old-school diner, Route 66 institution
A must-stop before hitting the road. This is where locals and travelers alike fuel up for the journey ahead.
ILLINOIS → BURR RIDGE / ROMEOVILLE AREA
Classic American Comfort Food Stops
Dell Rhea’s Chicken Basket (Willowbrook area)
Since: 1946
Famous for: Fried chicken
Featured on: Diners, Drive-Ins and Dives
White Fence Farm (Romeoville)
Since: 1954
Known for: Legendary fried chicken dinners
“As tender on the inside, crunchy on the outside… but also so light.”
This is more than a meal. It’s a full experience, complete with nostalgia, antiques, and family tradition.
ILLINOIS → JOLIET
Nostalgic Sweet Treat Stop
Rich & Creamy (Joliet)
Known for: Ice cream + retro Route 66 vibes
Bonus: Blues Brothers statues on the roof
A perfect quick stop for something sweet while soaking in Route 66 nostalgia.
ILLINOIS → BRAIDWOOD
Classic Drive-In Experience
Polka Dot Drive-In (Braidwood)
Since: 1950s
Must order: Burger, fries, milkshake
Surrounded by vintage cars and pop culture icons, this is peak Route 66 Americana.
Darley Newman Food Travel Pick: The Polk-a-Dot Drive In Along Route 66
ILLINOIS → SPRINGFIELD
One of Route 66’s Most Iconic Food Stops
Cozy Dog Drive In (Springfield)
Claim to fame: Birthplace of the “Cozy Dog” (not a corn dog!)
“These are not corn dogs… they’re cozy dogs.”
“Much more savory… with a little cumin, a little chili pepper.”
A must-stop for anyone doing a Route 66 food tour. This is history you can taste.
A Highlight For Foodies. Darley Newman at the Cozy Dog Drive In
Motorheads Bar, Grill & Museum (Springfield)
Known for: Beer, oversized pretzels, casual eats
Bonus: Route 66 memorabilia + community vibe
This is where food meets culture, cars, and community.
ILLINOIS → GIRARD
Hidden Gem Soda Fountain Stop
Doc’s Just Off 66 (Girard)
Origins: 1884 drugstore
Known for: Ice cream, soda fountain classics
“Still curing people after 150 years.”
From gooey butter cake ice cream to blackberry cobbler flavors, this stop blends history with indulgence.
ILLINOIS → LITCHFIELD
The Oldest Restaurant on Route 66
Ariston Café (Litchfield)
Since: 1924
Title: Oldest continuously operating restaurant on Route 66
Must try:
Prime rib (slow cooked 7–8 hours)
Pork tenderloin sandwich
Classic dessert trays
“We entertain thousands… for the Americana vibe.”
This is a cornerstone of Route 66 food culture.
ILLINOIS → LIVINGSTON AREA
Retro Diner + Sweet Treat Stop
Pink Elephant Antique Mall & Diner (Livingston)
Known for: Ice cream specialties (like “The Tornado”)
Experience: Vintage shopping + dessert
A fun, quirky stop that combines food with Route 66 nostalgia.
Why This Route 66 Food Journey Matters
Darley Newman’s Route 66 travels highlight something deeper than just great meals, they showcase the people, history, and community behind every stop.
“So many stops along Illinois Route 66 are in close proximity, making driving and stopping along the way easy and fun.”
From historic diners to family-run institutions, this stretch of Route 66 delivers one of the most authentic food travel experiences in America.
Plan Your Route 66 Foodie Road Trip
Whether you’re:
Searching for things to do near Chicago
Planning a Route 66 road trip itinerary
Looking for iconic American diners
Or simply craving a nostalgic food adventure
This Chicago-to-St. Louis route offers a perfect blend of history, flavor, and discovery, all curated by one of travel’s most trusted experts.
