Right around the Ozarks Arkansas/Missouri border area.
A city halfway between Midland TX and Chicago IL would be Tulsa OK, depending on your route.
Osceola, AR
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Rochester NY
Midland is the halfway point between Lexington South Carolina and Bennettsville.
Shelton Laurel, NC.
Enid Oklahoma
The halfway driving point lies on US 285, between Roswell, New Mexico and Vaughn, New Mexico
Thornton, IN
The halfway point between Chicago Illinois and Winnsboro Texas is Portageville, Missouri.
Van Buren Point, New York is halfway between Chicago & Montpelier
lisbon
Hubbard, OH
Cave, Missouri is halfway between Fayetteville & Chicago