Arch to Skyline: An Epic Road Trip from St. Louis to Chicago

A road trip from St. Louis to Chicago winds past several of the Midwest’s cultural landmarks, historical attractions, and scenic landscapes. As you pull away from the shadow of the iconic Gateway Arch and set your sights toward the bustling streets of the Windy City, check out these must-see experiences along the way.

Driving into Chicago at dusk.Photo byDepositphotos.

How Long is the Drive from St. Louis to Chicago?

The 300-mile drive from St. Louis to Chicago takes about 4.5 hours. However, the drive time may vary based on traffic conditions and route. And you’ll want to allow time to stop and explore the attractions that pique your interest from the list below.

The Gateway Arch and Old Court House in St. Louis.Photo bySage Scott.

Things to Do in St. Louis

St. Louis is a budget-friendly city full of free attractions. So before you load up these road trip games, pack up the car, and depart the Gateway City for the Windy City, take advantage of all St. Louis has to offer.

The Gateway Arch provides panoramic city views and is one of the nation’s newest national parks. For those looking for a unique experience, the City Museum is weirdly wonderful. It features an eclectic collection of local artwork and recycled materials, making it a playground for all ages. Outdoor enthusiasts will appreciate the Missouri Botanical Garden, and Citygarden, offering beautiful landscapes and art installations.

To experience the local food scene, get a taste of St. Louis at the City Foundry Food Hall. Under the roof of a renovated historical building, it brings a variety of eateries together in one unique spot. And don’t leave town without trying famous St. Louis foods like gooey butter cake, toasted ravioli, and St. Louis-style pizza.

Best Stops Between St. Louis and Chicago

Once you’ve explored the Gateway City, it’s time to hit the road for the Windy City. From exploring history and culture to experiencing scenic views and tasting delicious local cuisine, there are many things to discover along the way.

Litchfield

The Litchfield Museum & Route 66 Welcome Center is a must-visit for anyone traveling along iconic Route 66. This museum provides a comprehensive history of Litchfield, Illinois, highlighting the town’s contributions to the famous long road trip. Visitors can explore the town’s rich history through a variety of fun artifacts and displays, including vintage cars, old gas pumps, and neon signs. When you’re done exploring grab a bite at the Ariston Cafe. Serving locals and travelers since 1924, it’s one of the oldest continually-operational restaurants along Route 66.

A boy rubs Abraham Lincoln's nose for good luck.Photo byEnjoy Illinois.

Springfield

Famous for being Abraham Lincoln's birthplace, Springfield is home to attractions like the Illinois State Capitol and the Abraham Lincoln Presidential Library and Museum. Visitors can also visit Lincoln’s restored home and pay their respects at his tomb in the Oak Ridge Cemetery.

Bloomington

Bloomington, Illinois, is a popular stop for road trippers and history enthusiasts. Stop to visit the David Davis Mansion, a beautifully restored 19th-century estate, or stretch your legs at Miller Park Zoo. Shopping enthusiasts can head to Eastland Mall, featuring over 70 stores, and art lovers should keep an eye out for a wide range of delightful murals around town.

Starved Rock State Park

Nestled along the Illinois River, Starved Rock State Park is a 4,000-acre natural paradise with breathtaking canyons, stunning waterfalls, miles of hiking trails, and rich Native American history.

Roadside Attractions Between St. Louis and Chicago

The journey between St. Louis and Chicago is filled with unique roadside attractions. Pull over and snap a road trip selfie at these quick but quirky stops.

World's Largest Railsplitter Covered Wagon

This 24-foot-tall roadside attraction honors Abraham Lincoln’s legacy as a “railsplitter” and his influence on American railways. Visitors can marvel at the wagon’s intricate wood carvings, Lincoln’s statue, and immerse themselves in its rich historical context.

A larger-than-life roadside attraction in Atlanta, Illinois.Photo byDice Sales via Enjoy Illinois.

Paul Bunyan Hotdog Statue

This towering statue, located in Atlanta, Illinois, pays homage to the legendary American folklore character Paul Bunyan.

Gemini Giant

This 30-foot-tall statue in Wilmington is one of the most photographed landmarks along Route 66. The statue is currently being restored and will eventually be moved to a new location at South Island Park.

Things to Do in Chicago

Known for its iconic skyline, deep-dish pizza, and vibrant music scene, Chicago is full of exciting things to see and do. Consider purchasing a Chicago CityPASS to explore the Windy City for less, including these attractions.

Art Institute of Chicago

One of the world’s most renowned museums, the Art Institute of Chicago houses an impressive collection of over 300,000 works of art. Visitors can see works by masters such as Monet, Picasso, and van Gogh, as well as contemporary pieces and special exhibitions.

Sue, the world's largest and most complete Tyrannosaurus Rex skeleton on display at the Field Museum.Photo bySage Scott.

Field Museum

The Field Museum is a natural history museum that boasts over 40 million artifacts, including Sue, the largest and most complete Tyrannosaurus Rex skeleton ever discovered. In addition to dinosaurs, the museum also features exhibits on ancient civilizations, biodiversity, and the environment.

Lincoln Park Zoo

A family favorite, Lincoln Park Zoo offers free admission. It has over 1,100 animals on display, including big cats, primates, and penguins. Visitors can also enjoy a variety of interactive exhibits and experiences.

Millennium Park

This 25-acre park is a popular destination for locals and tourists alike. It features several notable art installations, including the iconic Cloud Gate sculpture, commonly known as “the Bean,” a reflecting pool and outdoor concert venues.

Navy Pier

Navy Pier was originally built as a shipping and recreation facility in 1916, but it is now a bustling entertainment destination that’s one of the best things to do in Chicago with kids. Visitors can enjoy a wide range of activities, from carnival rides and games to shopping, dining, and live performances.

From the Gateway Arch to Windy City Wonders

A road trip from St. Louis to Chicago is a journey brimming with fascinating cultural landmarks, historical sites, and natural beauty. Whether you’re drawn to quirky roadside attractions, the rich tapestry of American history, or the vibrant culinary scenes of two iconic cities, this route promises a unique adventure at every turn.