A LR35 PILOT REPORTS DEPARTING MDW WITH A CLRNC THAT INCLUDED LEWKE INTXN. A SIMILAR SOUNDING NEARBY INTXN LUKEY WAS ENTERED IN THE FMS; AND THE FLIGHT EXPERIENCED A TRACK DEVIATION.

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I CONTACTED MIDWAY CLEARANCE DELIVERY ON THE GROUND AND WAS GIVEN A FULL ROUTE CLEARANCE WITH ROUTING THAT WAS 'CLEARED TO CINCINATTI; LUNKEN FIELD VIA THE MIDWAY FOUR DEPARTURE; LEWKE; GIPPER; GIPPER 97 DEGREE RADIAL; 36 DME FIX; DIRECT FORT WAYNE...' I ASKED TOWER IF I COULD PULL OFF TO THE SIDE FOR A MINUTE AT THE END OF THE RUNWAY TO LOAD THE ROUTING; WHICH WAS APPROVED. THIS IS WHERE THE CONFUSION STARTED. I HAVE RECEIVED MANY CLEARANCES FROM MIDWAY AIRPORT THAT INCLUDED THE LUKEY INTERSECTION; SO I WAS FAMILIAR WITH THE SPELLING OF THAT NEARBY INTERSECTION. IN PREVIOUS FLIGHTS I HAVE ALWAYS BEEN GIVEN DIRECT DESTINATION BEFORE ACTUALLY FLYING TO LUKEY. AS I PUNCHED LUKEY INTO THE FLIGHT PLAN; IT SEEMED A LITTLE ODD TO BE HEADED SOUTH THEN EAST; BUT THE WHOLE ROUTING SEEMED STRANGE SO I DIDN'T REALLY QUESTION IT. AFTER TAKEOFF WE WERE GIVEN HEADING 090; THEN DIRECT LEWKE. I PUNCHED THE NAV MODE; WHICH WAS SET FOR LUKEY. AS WE TURNED TOWARD THE SOUTHEAST; THE OTHER PILOT QUESTIONED THE HEADING TO ME. I ASKED DEPARTURE FOR A HEADING WHILE WE STRAIGHTEN IT ALL OUT; WHICH THE CONTROLLER DID. WE FOUND LEWKE ON THE CHART; RESET THE FLIGHT PLAN; AND THE REST OF THE FLIGHT WAS UNEVENTFUL. OUR FLIGHT DIDN'T REALLY DEVIATE FROM THE ASSIGNED ROUTING; IT WAS JUST A MOMENT OF CONFUSION. THE PILOT IN THE RIGHT SEAT HAD FOUND LEWKE ON THE CHART BEFORE TAKEOFF; AND EVEN SPELLED IT TO ME. BUT AT THAT POINT I HAD ALREADY ENTERED IT INCORRECTLY; AND DIDN'T NOTICE THAT HE SPELLED IT DIFFERENTLY THAN I HAD. THIS COULD HAVE ALL BEEN AVOIDED BY MORE CAREFUL STUDY OF THE FLIGHT PLAN; BUT IT DIDN'T OCCUR TO ME THAT THERE WOULD BE TWO LUKEY'S IN CLOSE PROXIMITY TO MIDWAY. LUKEY IS 72 MILES SOUTH-WEST OF MIDWAY; AND LEWKE IS 31 MILES EAST. IN MY OPINION HAVING TWO FIXES THAT SOUND IDENTICAL IN THE SAME AREA IS SETTING THE STAGE FOR CONFUSION; WHICH COULD BE A SAFETY ISSUE IN THE BUSY AIRSPACE SURROUNDING CHICAGO.