The Best Road Trip From Chicago to St. Louis

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This one-day road trip from Chicago, Illinois to St. Louis, Missouri will give you a chance to take in the best of the Midwest!
A stop along the way in Bloomington, IL breaks up this 300-mile trip into two even segments and offers a chance for you to peruse the land of Abe Lincoln and Beer Nuts. Whether you’re a history buff, an architecture lover, or a thrill-seeker, this entertaining road trip will have you cheering “Meet me in St. Louis!”
Before you take to the road, make sure you feel confident with your car insurance policy. Check out Jerry, a licensed insurance broker app that can find you the best coverage for your money from the top 50 auto insurance providers in under a minute. Jerry even offers an emergency roadside assistance program that ensures you have access to emergency assistance, vehicle towing, and other important services when you’re in a pinch on the road.
Get ready to discover the ultimate one-day road trip from Chicago to St. Louis!
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Chicago, IL to Bloomington, IL

Driving time: 2.25 hours
Wave goodbye to the Windy City and head southwest toward the land of Lincoln. The first leg of your day trip will take you from one Illinois city, Chicago, to another, Bloomington. With the majority of the trip spent on Interstate 55, you’ll appreciate stopping in a city so hip it’s referenced in two of Sufjan Stevens’s songs.
Must do: Add some whimsy to your trip through the Bloomington-Normal area by visiting the Children’s Discovery Museum. Children and fun-loving grown-ups will find tons of interactive exhibits that are both educational and entertaining. While there, don’t miss AgMazing, the country’s largest agricultural exhibit at a children’s museum, where visitors can harvest corn, steer a combine, and feed livestock.
Other popular exhibits include Health Me!, a kids’ medical exhibit, and Dig It!, an outdoor exhibit where visitors can dig for dinosaur fossils and scale a climbing wall. Children can also unleash their creativity in the Art Studio or Paint Wall and participate in a variety of free science activities in the FETCH! Lab.
Must see: Tour the David Davis Mansion State Historic Site, a three-story, thirty-six-room, yellow-brick Victorian home built between 1870 and 1872 by the distinguished lawyer, Supreme Court justice, and senator, David Davis. Davis is famous for his close connection with Abraham Lincoln, who practiced law in Bloomington.
Also known as Clover Lawn, this gorgeous National Historic Landmark includes indoor and outdoor sites to explore and artifacts that tell the story of one prosperous Victorian family and their influence on American politics.
Must eat: Grab lunch at Ancho & Agave, a spacious, inviting Mexican restaurant that serves plates made with fresh, high-quality ingredients and plenty of flair. Satisfy your flavor cravings with their house-made signature salsas, tortilla chips, and guacamole—but save room for their delectable street and avenue tacos!
A lawn walkway leads to the Victorian Davis Mansion in Bloomington.
Davis Mansion, Bloomington

Bloomington, IL to St. Louis, MO

Driving time: 2.5 hours
Continue on from Bloomington to St. Louis, Missouri, the birthplace of T. S. Eliot. Known as the “Gateway to the West,” St. Louis boasts more free major tourist attractions than any other US city (other than Washington, DC).
Must do: Explore City Museum, an industrial and architectural museum housed in a hundred-year-old shoe warehouse in downtown St. Louis. This one-of-a-kind specialty museum contains four floors of installations and curiosities made by industrial artists.
Bring your flashlight and wear closed-toed shoes—you’ll need them for the thirty-plus slides (including a ten-story one!), enchanted caves, miles of tunnels, outdoor climbing area, “Artquarium,” model train exhibit, and architectural museum. If you’re not afraid of heights, head up to the rooftop to check out the school bus that overhangs it and take a ride on the Big Eli Ferris Wheel.
Must see: No trip to St. Louis is complete without a visit to the Gateway Arch, which, at 630-feet tall, is the world’s tallest arch and the tallest man-made monument in the Western Hemisphere. Stretch your legs on the grounds of Gateway Arch National Park, or see the city from a whole new angle from the Tram Ride to the Top.
Must eat: St. Louis is famous for its toasted ravioli, and the restaurant often credited with inventing this decadent dish is Charlie Gitto’s On the Hill. This 40-year-old St. Louis landmark serves authentic Italian food sure to please everyone from the pizza lover to the risotto connoisseur.
The Gateway Arch reflects onto a river near St. Louis with the city behind it.
Gateway Arch, St. Louis

Why you need roadside assistance

Even a day trip can be thwarted by a roadside breakdown. Jerry is here to help you get to your destination with ease, safety, and confidence. Jerry’s roadside assistance program features:
  • Emergency roadside assistance
  • Vehicle towing up to 10 miles
  • Jumpstarts
  • Tire changes
  • Lockout assistance
  • Fuel delivery
  • Winching
  • Roadside reimbursement
  • Rental vehicle roadside reimbursement
Roadside assistance is the best and cheapest ($6.99) way to make sure that your road trip goes as smoothly as possible.

Finding affordable car insurance

Don’t leave home without ensuring you have the protection you need for your car or rental vehicle. Jerry can find you cheap car insurance with the best coverage in under a minute.
Drivers who use Jerry’s AI-based insurance broker app save an average of $879 a year! And the best part…Jerry is completely free to use. So what are you waiting for? Download the Jerry app now and get competitive quotes in under a minute.
“I went into the app thinking I wouldn’t change my insurance, but boy was I wrong! I received a quote for half of what I was paying and was able to add roadside assistance at the same time. I’m so glad I gave this a try!”—Satisfied Jerry user
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