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

The chicago skyline at dusk.

A road trip from St. Louis to Chicago will wind 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.

This drive from St. Louis, MO, to Chicago, IL, isn’t just a journey between two cities. It is an exploration of the cultural and historical heartbeat of the Midwest. You’ll encounter profound historical sites, meander along stretches of historic Route 66, spot quirky roadside attractions, and have the opportunity to indulge in mouthwatering local eats. So, rev up your engine, and let’s explore the unforgettable slices of Americana that bring this journey to life. 

Road trip from st chicago.


Have You Driven from St. Louis to Chicago?

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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 in st louis.
Photo Credit: Sage 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 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. 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. 

The Ariston Cafe in Litchfield, IL, is a great stop on a road trip from Chicago to St. Louis.
Photo Credit: Steve from Pixabay


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.

Related Article: Get Your Kicks with These Route 66 Quotes and Captions

A woman taking a picture of a bust of Abraham Lincoln in Springfield, Illinois.
Photo Credit: Ryan Donnell for Meredith Corporation via Enjoy Illinois.


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.

See all the Springfield sights with this self-guided audio tour that lets you explore at your pace.

“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.”

A woman walks past a building with a mural on it in Bloomington, IL.
Photo Credit: MoneyforCoffee from Pixabay


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.

“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.” 

The Lasalle Falls waterfall at Starved Rock State Park in Central 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.

Abe Lincoln sitting on the world's largest railsplitter covered wagon along Route 66 in Illinois.

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 statue of a larger than life Paul Bunyan with a hot dog along Route 66 in Illinois.
Photo Credit: Dice Sales via Enjoy Illinois.

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 is a statue along Route 66 in Illinois.
Photo Credit: Illinois Office of Tourism.

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.

Chicago skyline at dusk.
Photo Credit: YayImages.

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.

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A woman admiring a painting of Liz Taylor by Andy Warhol at the Chicago Art Institute
Photo Credit: CityPASS.

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 at the Field Museum in Chicago
Photo Credit: Sage 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. As well as dinosaurs, the museum also features exhibits on ancient civilizations, biodiversity, and the environment.

A zebra standing next to a tree at the Lincoln Park Zoo.
Photo Credit: YayImages.

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.

Cloud Gate, or The Bean, in Chicago, Illinois.
Photo Credit: Illinois Office of Tourism.

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.

People enjoying rides at Navy Pier in Chicago, Illinois.
Photo Credit: Adam Alexander via the Illinois Office of Tourism.

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.

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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.

Have You Driven from St. Louis, MO, to Chicago, IL?

What did you like most? What time of year did you make the trip? Do you have any additional tips or tricks to pass along? Share your experiences in the comments section below.

Portions of this article originally appeared on Food Drink Life.

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5 thoughts on “Arch to Skyline: An Epic Road Trip from St. Louis to Chicago”

  1. I’ve been looking for more places to visit in Chicago, I’ve already got the Art Institute and of course, The Bean, in my itinerary! I can’t wait to check out the others!

  2. OK, I was looking for exactly this itinerary for a road trip we’re taking for my grandfather’s 90th birthday, and this couldn’t have come at a better time!!! I never even thought about stopping in Bloomington but I bet my kids are going to love it. Thanks for this compilation, it made my trip!

  3. I love reading about your adventures!! There are so many great things to see and do. Thank you for step by step things to see, buy, and do on my way to Chicago!

  4. I grew up in Bloomington and loved reading all the places you recommend.
    I cannot wait to go to some of the other places you mention on the roadtrip.
    So much information, I love articles like this.

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