ZAU CTLR MISINTERPS B757 ROUTING; EXPECTING A DIFFERENT DIRECTION TURN; RECOGNIZING ERROR WHEN CONFLICT DEVELOPS WITH HS25 IN DSCNT.

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I HAD ASSUMED THE 'PMM-R' CTLR POS ONLY 3 OR 4 MINS PRIOR TO THE ERROR. DURING THE RELIEF BRIEFING; I HAD BEEN TOLD THAT ACR X (ACFT #1) HAD BEEN HANDED OFF AND SWITCHED TO THE SUPER HIGH SECTOR ABOVE ME; (REQUESTING FL350) - MY OWN SECTOR ONLY GOES TO FL310. BEFORE I COULD EVEN SIT DOWN; THE SUPER HIGH CTLR CALLED ME TO SAY THAT ACR X HAD REQUESTED TO LEVEL AT FL310; AND I APPROVED THIS. BECAUSE ACR X HAD BEEN SWITCHED TO THE OTHER CTLR; THE FLT PROGRESS STRIP HAD BEEN TORN DOWN. I THOUGHT THAT ACR X WAS ROUTED PMM.J94..OBK. ACR Y WAS HANDED TO ME AT FL330; DIRECT LAN; A COURSE THAT TOOK HIM W TO E; ABOUT 10 NM N OF PMM. I DSNDED ACFT Y TO FL280 AND WENT TO SEQUENCE NEW FLT STRIPS. WHEN I NEXT LOOKED AT MY RADAR; ACR X HAD TURNED FROM PMM TOWARD BAE (BADGER; WI). AT THIS POINT I STILL THOUGHT ACR X WAS SUPPOSED TO TURN L; SW; AT PMM; NOT NW. I TURNED ACR X TO A 260 DEG HDG AND ACFT Y TO TURN L 20 DEGS AND TO EXPEDITE HIS DSCNT. AFTER SEPARATION HAD BEEN RESTORED; BOTH ACFT WERE PUT BACK ON COURSE. ACR X RTE; DTW.DUNKS.J70.BAE.EAU4.MSP. ACFT Y RTE; LAS.DSM.LAN.SPRTN3.DET.