What's the best route from Chicago to San Antonio?

Call it childhood nostalgia, but I’ve always wanted to visit San Antonio because of Pee-wee’s Big Adventure. I have two weeks to make the trip, so I’m going to drive. What’s the best driving route from Chicago to San Antonio?

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Answer provided by
Eric Schad
Answered on May 17, 2022
Don’t be too shocked when you get there—there’s no basement in the Alamo! It’s going to take you about 18 hours to cover 1,200 miles, but if you’re up for the challenge, the best driving route from Chicago to San Antonio is:
  • Hop on I-57 South from Chicago.
  • Take exit 1A near Sikeston, Missouri, to get on I-55 South.
  • Stay on I-55 South until you reach West Memphis, Arkansas, then take exit 8 for I-40 West.
  • Merge onto I-30 West just north of Little Rock.
  • In Dallas, take exit 46A onto I-35E.
  • Merge onto I-35 South near Hillsboro, Texas and this will take you straight into the Alamo City.
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