The Best Road Trip From Chicago to St. Louis

This one-day road trip from Chicago, IL, to St. Louis, MO, will have you enjoying some of the best sights and eats that the Midwest has to offer.
Written by Jennifer Yirinec
Reviewed by Carrie Adkins
This one-day road trip from Chicago,
to St. Louis,
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
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Key trip details

Chicago, IL to St. Louis, MO
​​Distance: 297 miles
Driving time: 4 hours and 48 minutes
Suggested length of trip: 1 to 3 days


  • Chicago, IL—Half a day
  • Bloomington, IL—One half to 1 day
  • St. Louis, MO—1 to 2 days

Chicago, IL to Bloomington, IL

135 miles, 2 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
city, Chicago, to another, Bloomington. Though it might seem unassuming, you’ll appreciate stopping in a city so hip it’s referenced in two of Sufjan Stevens’s songs.
To get to Bloomington, follow I-55 S and take the US-51 BUS exit.

Where to eat in Bloomington

  • The Runcible Spoon
    ($$): Check out this bustling option for casual breakfast fare and delicious coffee! It’s a cozy, whimsically decorated hideaway that makes for the perfect morning pitstop.
  • Ancho & Agave
    ($$): 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!

What to do in Bloomington

Davis Mansion
  • Children’s Discovery Museum
    : Add some whimsy to your trip by visiting this exciting museum. Children and fun-loving grown-ups will find tons of interactive exhibits that are both educational and entertaining. Some of their fun exhibits include Health Me!, Art Studio, and AgMazing, where you can harvest corn, steer a combine, and even feed livestock.
  • David Davis Mansion State Historic Site
    : Tour this yellow-brick Victorian home built in the late 1800s. 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.

Bloomington, IL to St. Louis, MO

162 miles, 2.5 hours
Continue on from Bloomington to St. Louis,
, 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).

Where to eat in St. Louis

  • Charlie Gitto’s On the Hill
    ($$-$$$): St. Louis is famous for its toasted ravioli, and the restaurant often credited with inventing this decadent dish is Charlie Gitto’s. This 40-year-old St. Louis landmark serves authentic Italian food sure to please everyone from the pizza lover to the risotto connoisseur.
  • Hendel’s
    ($$): Situated in a converted general store built in the late 1800s, head here for classic and creative American fare, a full bar, and a lively, welcoming atmosphere.

What to do in St. Louis

Kiener Memorial Fountain
  • Visit the Gateway Arch
    : 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.
  • Tram Ride to the Top
    : For a view unlike any other, take this 45-60 minute ride to the top of the Gateway Arch, learning about the history of the monument along the way!
  • City Museum
    : Explore this one-of-a-kind industrial and architectural museum housed in a hundred-year-old shoe warehouse in downtown St. Louis. With four floors of installations and curiosities made by 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, and outdoor climbing areas.

Why you need roadside assistance

Even a day trip can be thwarted by a roadside breakdown.
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  • 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.

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