Embarking on a road trip down Illinois’s iconic Route 66 promises an adventure infused with nostalgia, breathtaking landscapes, and a taste of American history. The Mother Road, as Route 66 is affectionately known, weaves through the heart of Illinois, offering a one-of-a-kind journey filled with quirky roadside attractions, charming towns, and a rich cultural tapestry. There’s so much to explore here that it would be easy to get lost among the attractions and fill a two-day, three-day, four-day, or even seven-day agenda with the plethora of things to see. But, if you have limited time, this Illinois Route 66 1-Day road trip itinerary is for you.
If you only have 24-hours in your travel itinerary to drive all the way through Illinois, from Chicago to St. Louis, you might have to spend more time on the highway than the byway. At about 300 miles, it will take you around 4 hours, 45 minutes of pure driving time, and that is with taking the higher-speed highway! So plan to leave early, arrive late, and prioritize the stops and experiences that are most meaningful to you. Keep in mind that when you are traveling in the bigger cities on the route, like Chicago, Springfield, and St. Louis, that rush hour traffic can add to your time on the road!
Buckle up and explore our Illinois Route 66 1-Day road trip itinerary to make the most of your exploration along this historic highway.
Illinois Route 66: 1-Day Road Trip Itinerary
There are plenty of Illinois Route 66 attractions to see as you traverse the state from Chicago to St. Louis, Missouri. So much so that you’ll wish you had more than 24 hours to make the journey. But if you only do have one day, you’ll want to make the most of it!
Below is an Illinois Route 66 1-Day road trip itinerary that calls out some of the highlights worth pulling over for. Depending on when you leave in the morning, how bad traffic is, and how long you spend at each location, you might not have time to explore them all. But whether you love roadside attractions, history, museums, or food, there’s something here for everyone to love.
The Road Begins Here Sign at Navy Pier
On March 25, 2026, the city of Chicago moved the “official” starting point to Navy Pier. This move marked the tourist attraction as the symbolic Beginning of the Trail, creating a pier-to-pier journey from Navy Pier in Chicago to the Santa Monica Pier in Santa Monica. A new sign marks the spot in front of Harry Caray’s Tavern and, inside you’ll find a new Route 66-themed mural.
Historic Route 66 Begin Sign
Start your morning by checking out of your downtown Chicago hotel and grabbing a quick selfie at the Historic Route 66 Begin Sign before heading to see the rest of Route 66 in Chicago.
Route 66 Interpretive Signs
At the start of Route 66 in Chicago you can now also find several new interpretive signs starting on Michigan Avenue, across the street from the Art Institute of Chicago, and continuing in three Chicago neighborhoods along Route 66.
Lou Mitchell’s Restaurant
Before starting your long drive, stop for a delicious diner breakfast at Lou Mitchell’s Restaurant down the road. On the days they are open (Wednesday-Sunday) they start serving breakfast at 6am or 7am, get there early to avoid a crowd and to get a head start on your drive! With only one day in Illinois, you have a lot of ground to cover!
Joliet Area Historical Museum and Route 66 Welcome Center
There are several fun sites to see in Joliet, Illinois, like Dick’s Towing Service, the Illinois Rock & Roll Museum on Route 66, Old Joliet Prison, and Rich & Creamy. With only one day to traverse Illinois on Route 66, you probably won’t have time to explore them all. If you do have time, stop by the Joliet Area Historical Museum and Route 66 Welcome Center with exhibits on The Mother Road, the Blues Brothers, and more.
Gemini Giant Muffler Man
The Gemini Giant Muffler Man in Wilmington, Illinois is a 28-foot tall muffler man who once stood outside the Launching Pad restaurant. The Route 66 roadside attraction weighs 438 pounds: not counting his base or the giant 8-foot rocket he holds in his hands! Stop here for some quick photos with this famous Route 66 roadside attraction.
Odell Historic Standard Oil Filling Station
You’ll probably have to stop for gas at least once on your 1-day Illinois Route 66 itinerary. Unfortunately, you won’t find any fuel pumping at this vintage service station. You will, however, see a piece of history at the Standard Oil Filling Station in Odell, Illinois. The structure was built in 1932 and now operates as a welcome center and visitor center for the town.
Illinois Route 66 Hall of Fame and Museum
The Illinois Route 66 Hall of Fame & Museum in Pontiac, Illinois tells the story of the Mother Road from its inception to the present day with thousands of artifacts, memorabilia, articles, and more. Stop in to learn about all of the famed stops, places, and people who have been inducted into the Illinois Route 66 Hall of Fame. Highlights include booths from the world’s first Steak and Shake, artist and traveler Bob Waldmire’s VW Van, displays on all the classic must-see Route 66 stops, vintage gas pumps, maps, and more.
Route 66 Shield Mural
After exploring the Route 66 Hall of Fame Museum, step outside to take pictures with the giant Route 66 Shield Mural. You can even drive your car up in front of it! More than 20 more Murals on Main Street are painted around the historic Pontiac downtown, giving the town the moniker, Route 66 Mural City. Look for a few more murals surrounding the museum.
Paul Bunyon Hot Dog Muffler Man
The Paul Bunyon Hot Dog Muffler Man in Atlanta, Illinois is one of the most recognizable roadside attractions on Route 66. Visit this Tall Paul then head across the street to check out the new American Giants Museum.
American Giant Museum
The American Giants Museum in Atlanta, Illinois pays tribute to Muffler Men and other oversized fiberglass creations that once were a mainstay of American advertising. Stop inside to learn more about muffler men and check out the giant examples outside: the Snerd Giant, Texaco Big Friend, Phillips 66 Cowboy, Space Man, Indian Brave,, and Carpet Viking.
World’s Largest Railsplitter Covered Wagon
The World’s Largest Railsplitter Covered Wagon in Lincoln, Illinois is a giant wagon topped with an equally giant Lincoln on Route 66. If you have the time and want to learn more about Abraham Lincoln on your Illinois Route 66 road trip, there are plenty more attractions in Lincoln and Springfield that you can potentially add to your itinerary, including Lincoln’s Tomb, Lincoln Home National Historic Site, The Old State Capitol, Lincoln County Courthouse, Abraham Lincoln Presidential Library and Museum, Lincoln Watermelon Monument, and the Abe Lincoln Rail Splitter Statue at the Illinois State Fairgrounds.
Route 66 Donut
While in Lincoln, make a stop at Mel-O-Cream Donuts for a long john or fritter, and don’t miss the giant chocolate donut in the parking lot! This upright, oversized treat is big enough to sit inside, complete with the town name and a Route 66 shield for the perfect photo op.
Lauterbach Giant
Not sick of muffler men yet? Good. Visit the Lauterbach Giant in Springfield, Illinois. This Route 66 Muffler Man has stood in the parking lot outside Lauterbach Tire & Auto Service since 1978.
Cozy Dog Drive In
By the time you get to Springfield, you’ll surely be hungry for lunch. Stop for a meal at Cozy Dog Drive In. Their signature item is a battered and fried hot dog on a stick, but they make it clear that Cozy Dogs preceded the modern corn dog and are superior in quality and taste to your normal cornmeal-dipped fair dog.
Original Route 66 Brick Road
Even if you’re mostly sticking to the highway on your Illinois Route 66 1-day road trip itinerary, be sure to pull off in Auburn to drive on the Original Route 66 Brick Road (also known as Brick 66), 1.4 miles of hand-laid brick road from 1931. Enjoy the drive then find some more attractions in the afternoon.
Litchfield Museum & Route 66 Welcome Center
Stroll through Litchfield, Illinois and take photos with the Greetings From mural. Then pop into the Litchfield Museum & Route 66 Welcome Center to learn more about Litchfield and its part of Route 66 history. Find exhibits on how Route 66, railroads, businesses, agriculture, and the military have shaped the area.
Soulsby Service Station
Soulsby Service Station in Mount Olive, Illinois is a historic gas station that served Route 66 travelers for decades. This site is one of the oldest and longest-running service stations on all of Route 66 and the oldest usable service station on the highway in Illinois. Be sure to step inside to view a museum of artifacts, including vintage gas canisters, a soda machine, and old signs.
Pink Elephant Antique Mall
At the Pink Elephant Antique Mall in Livingston, Illinois you can find their famous big pink elephant roadside attraction and also so much more. Housed in a former high school, this location now serves as a flea market with more than 50 antique dealers. Scour the tables inside for treasures, grab some ice cream at the diner, and take photos of the big attractions outside.
Old Chain of Rocks Bridge
Your final destination on this Illinois Route 66 1-day road trip itinerary takes you to the border of Missouri. Old Chain of Rocks Bridge was once an essential part of the cross-country journey, taking travelers from Illinois, across the Mississippi River, and into Missouri. While you can no longer drive across this famous bridge, if you arrive before sunset, it’s still worth a trip to walk across and admire.
After walking across Old Chain of Rocks Bridge, turn around and prepare to cross a newer bridge into Missouri. After a long day on the road it’s time to find dinner and check into your hotel for the night. Even though this is an Illinois Route 66 itinerary, if you’re driving westbound, you’ll probably want to spend the night in St. Louis, Missouri. If you’re looking for dinner consider ordering a local St. Louis–style pizza! The unique pie has a thin, cracker-like crust and is topped with Provel cheese! You can find it at several local establishments, including a favorite chain, Imo’s Pizza. Don’t forget dessert! Stop at Ted Drewes Frozen Custard for their famous frozen custard!
Where to Stay in St. Louis, Missouri
If you’re driving the full length of Illinois Route 66 in one day, your best bet for a place to spend the night is just over the border in St. Louis, Missouri.
While there aren’t any specific Route 66 hotels in St. Louis, there are a lot of hotels with a history as long as the road. For a special stay, book a room at a historic downtown hotel with a past, like the St. Louis Union Station Hotel, Drury Plaza Hotel St. Louis at The Arch, or Magnolia Hotel St. Louis.
St. Louis Union Station Hotel
An icon since 1894, the St. Louis Union Station is a vintage gem wrapped in elegant archways and décor. Admire the famous Grand Hall, experience all the on-site attractions, enjoy 3D light shows and a 100-foot waterfall, and access the fitness center and seasonal outdoor pool. All just a mile from downtown St. Louis.
Drury Plaza Hotel St. Louis at The Arch
If you want to find a hotel close to the Gateway Arch, you can’t do any better than the Drury Plaza Hotel St. Louis at The Arch. This St. Louis hotel is located less than a five-minute walk to the Gateway Arch and Busch Stadium, at the heart of downtown. Enjoy 37-inch flat-screen TVs, free Wi-Fi, an indoor pool and hot tub, and a free hot breakfast.
Magnolia Hotel St. Louis
Listed on the National Historic Register, Magnolia St. Louis was originally built in 1924 as the Mayfair Hotel by Charles Heiss, with hospitality and sophistication in mind. This hotel is known as the birthplace of “chocolates on a pillow,” a tradition influenced by actor Cary Grant’s tryst within his suite.
Want more St. Louis Route 66 hotels? Explore more here and peruse reviews.
Where to Stay in Chicago, Illinois
Chicago will be the start (or end) of your Route 66 road trip across Illinois. And, if you’re beginning your Route 66 road trip in Chicago, you’ll probably need a place to spend a night or two. For a special start to your Illinois Route 66 road trip, book a room at one of these downtown Chicago hotels.
Downtown Chicago hotels can be pricy, and they do not include parking (which is also pretty pricy). So if you’re roadtripping on a budget you might want to forgo spending the first night in Chicago and wait until you’re out of the city to find more budget-friendly accommodations with free parking lots.
But if you want to kick off your road trip with a night exploring Chicago, add one of these Chicago Route 66 hotels to your travel itinerary.
The Blackstone
Opened in 1910, The Blackstone was once known as “The Hotel of Presidents,” having hosted several heads of state (including Teddy Roosevelt and Jimmy Carter), along with a slew of celebrities, like the Rockefellers, the Vanderbilts, Lena Horne, Nat King Cole, Rudolph Valentino, and Al Capone. The historic landmark and architectural wonder has been renovated to appease the contemporary traveler and offers 335 accommodations
Congress Plaza Hotel
Located near the start of Route 66, the Congress Plaza Hotel has been in operation since 1893 and is a welcoming stay for the beginning of your journey on the Mother Road.
Palmer House Hilton
Located just steps from Route 66, Palmer House Hilton is a luxurious historic hotel with all the modern conveniences you could desire alongside award-winning services. Palmer House was built in 1925 and was the city’s first hotel with elevators, electric light bulbs, and telephones in the guest rooms. The French neo-classical influences of the design give this landmark its distinctive charm.
The Gwen
The Gwen is a luxury hotel in the heart of downtown Chicago with a historic facade crafted by sculptress Gwen Lux in 1928. The property offers two on-site restaurants, a rooftop terrace, a state-of-the-art fitness center, and modern rooms with large flat-screen TVs, free WiFi, and custom décor inspired by signature sculptures.
Freehand Chicago
Located in the River North neighborhood, just one mile from the beginning of Route 66, Freehand Chicago is a hip hotel featuring unique designs, a fun atmosphere, and happy hour specials at the on-site bar, Broken Shaker. Freehand is housed in a 1927 building that originally operated as the Devonshire Hotel.
Want more Chicago Route 66 hotels? Explore more here and peruse reviews.
Map of Illinois Route 66
Explore our full map of Route 66 in Illinois below. For easy browsing, it is categorized and color-coded by category: roadside attraction, dining, landmark, museum, outdoors, mural/sign, accommodation, shopping, and tour/excursion.
