The Rangers optioned Olt to the Round Rock Express of the Class AAA Pacific Coast League (PCL) during spring training in 2013. He struggled to begin the season, batting .139 through April 25. He reported problems with depth perception, which specialists indicated could be the result of a concussion. When it was discovered that a lacrimal gland wasn't producing tears, he was given eye drops, which corrected the vision problem. He returned to Round Rock on June 3.
After batting .213 at Round Rock, the Rangers traded Olt to the Chicago Cubs on July 22, 2013, with Justin Grimm, C. J. Edwards, and a player to be named later (Neil Ramirez), in exchange for Matt Garza. Olt reported to the Iowa Cubs of the PCL. He batted .168 in 152 plate appearances with Iowa. He attempted to find a new way to treat his vision problem, as the eye drops he was given raise the chances of developing glaucoma.