Arch to skyline: An epic road trip from St. Louis to Chicago

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Use this guide to embark on a scenic road trip from St. Louis to Chicago. Your journey will wind through the Midwest’s cultural landmarks, historical attractions and scenic landscapes.

Traffic flowing to and from downtown Chicago at dusk.
Photo credit: YayImages.

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 surrounded by trees.
The Gateway Arch in St. Louis, Missouri. Photo credit: Sage Scott.
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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 gamespack 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. Outdoors 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.

A historic automobile on display at the Litchfield Museum.
Exhibit at the Litchfield Museum. Photo credit: Olio in Iowa.

Litchfield Museum & Route 66 Welcome Center

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.


Famous for being the birthplace of Abraham Lincoln, 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.

“When you’re passing through Springfield, the Old State Capitol, Lincoln’s Grave and Lincoln’s Home are obligatory stops for history buffs. The Capitol and Home offer tours, while the monument is something you can easily explore on your own.”

— Michelle Price, Honest and Truly


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.

“Bloomington’s walkable downtown is picturesque and full of character and murals. Be sure to grab a coffee and a pastry at the local Coffee Hound while you’re there.”

— Susannah Brinkley Henry, Feast + West
Steep stone cliff in a canyon of Starved Rock State Park in Illinois.
Steep stone cliff at Starved Rock State Park in Illinois. Photo credit: YayImages.

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.

A statue of Abraham Lincoln riding a large covered wagon at a roadside attraction in Illinois.
World’s Largest Railsplitter Covered Wagon. Photo credit: Olio in Iowa.

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. 

Paul Bunyan Hotdog Statue

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

The Gemini Giant

This 30-foot tall statue in Wilmington, Illinois, is named after the Gemini space program and is one of the most photographed landmarks on Route 66.

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 T-Rex on display at The Field Museum in Chicago.
Sue the T-Rex at the Field Museum in Chicago. Photo credit: Sage Scott.

Field Museum

The Field Museum is a natural history museum boasts over 40 million artifacts, including Sue, the largest and most complete Tyrannosaurus Rex skeleton ever discovered. As well as 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

Originally built as a shipping and recreation facility in 1916, Navy Pier is now a bustling entertainment destination. Visitors can enjoy a wide range of activities, from carnival rides and games to shopping, dining and live performances.

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.

Sage Scott was bitten by the travel bug as a preschooler when her family moved abroad for the first time. Now settled in America’s Heartland, Sage is a travel writer, world wanderer and photographer whose favorite color is golden hour. Follow her adventures at Everyday Wanderer.

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