INSTRUCTOR AND STUDENT PLT ON PA27 STRUGGLE TO EXIT ORD CLASS B AIRSPACE WITHOUT BREAKING ALL THE RULES. DON'T QUITE SUCCEED.

Narrative

THE R SEAT WAS OCCUPIED BY MYSELF; A CFI/MEI CONDUCTING A DUAL TRAINING FLT IN A PIPER AZTEC PA27-250 WITH A TWIN RATED COMMERCIAL PLT IN THE L SEAT. THE L SEAT PLT WAS THE SOLE MANIPULATOR OF THE CTLS. I WAS PROVIDING DUAL INSTRUCTION FOR THE PLT WHO DID NOT YET MEET SCHOOL RENTAL MINIMUMS TO SOLO THE PLANE. THE TIME WAS ABOUT XA30 UTC AND WE HAD DEPARTED ORD VFR ON RWY 14. THE VFR CLRNC STATED THAT 1800 FT WAS TO BE MAINTAINED UNTIL CLR OF CLASS B AIRSPACE. SHORTLY AFTER LEVEL ON A HEADING OF ABOUT 145 DEGS; CHICAGO DEP CTL INFORMED THE PLT TO SQUAWK VFR WITH FREQ CHANGE APPROVED. AT THE TIME THE ACFT WAS A SHORT DISTANCE FROM MIDWAY CLASS C AIRSPACE. I TUNED IN MIDWAY APCH CTL AND MADE A CALL BUT GOT NO ANSWER. (THE FREQ WAS VERY BUSY.) SINCE THE HEADING WAS ABOUT TO PUT THE ACFT INTO MIDWAY CLASS C AIRSPACE WITHOUT THE REQUIRED 2-WAY COMS; I ORDERED A TURN N TO PARALLEL THE DOWNTOWN AREA. (THE GPS MAP SHOWED THE PLT'S ACFT CLOSE TO BUT NOT TOUCHING THE CLASS C. I WAS AWARE THAT GPS MAPS ARE NOT RELIABLE IN THESE CIRCUMSTANCES; SO HE ORDERED THE TURN.) AFTER PASSING THE TALL BUILDINGS; I THEN ORDERED A TURN E TOWARD THE LAKE MICHIGAN SHORELINE. THE NEW HEADING KEPT THE ACFT W OF THE MAIN DOWNTOWN CHICAGO AREA WITH THE BIG BUILDINGS. EVEN SO; IT APPEARED TO ME THAT AS THE ACFT PROCEEDED N AND THEN E AROUND THE MAIN DOWNTOWN AREA; THE REQUIRED 1000 FT ABOVE THE HIGHEST OBSTACLE WITHIN A HORIZ RADIUS OF 2000 FT OVER A CONGESTED AREA WAS PROBABLY NOT MAINTAINED. THE ACFT NEVER WENT BELOW THE 1800 FT ALT RESTR ASSIGNED BY ATC. WE WERE AWARE THAT WE WERE NO LONGER IN CLASS B; BUT WERE NOT FAMILIAR ENOUGH WITH THE LANDMARKS TO BE SURE WHERE THE CLASS B SHELF AREA TRANSITIONED FROM 1900 FT TO 3000 FT. THEREFORE; WE WERE RELUCTANT TO CLB AND SO MAINTAINED THE 1800 FT MSL UNTIL REACHING THE SHORELINE WHERE THEY CLBED TO 2500 FT MSL. FROM THERE THE PLT TURNED THE ACFT SE AND PROCEEDED ALONG THE SHORELINE PAST GARY (CONTACT WAS MADE WITH GARY TWR) AND THEN WITHOUT INCIDENT NE TO SOUTH BEND; IN; WHERE THE AIRPLANE LANDED. THE O'HARE TURNAROUND TOOK MORE TIME THAN I HAD PLANNED AND THEREFORE THE SUBSEQUENT LNDG AT SOUTH BEND AND THEN ON TO ANDREWS UNIVERSITY AIRPARK (C20) MAY HAVE VIOLATED THE NIGHT TKOF AND LNDG RULE; SINCE THE CFI WAS NOT AT THE TIME NIGHT CURRENT IN AN AIRPLANE MULTI-ENG LAND. IN SUMMARY; I AM CONCERNED THAT THESE THINGS MAY HAVE HAPPENED: 1) AN INADVERTENT VIOLATION OF MIDWAY'S CLASS C AIRSPACE MAY HAVE TAKEN PLACE; 2) THE REQUIRED MSA WAS NOT MAINTAINED OVER A CONGESTED AREA; AND 3) AN INADVERTENT VIOLATION OF THE NIGHT CURRENCY REQUIREMENT MAY HAVE TAKEN PLACE. CONTRIBUTING FACTORS: MY UNFAMILIARITY WITH PROCS AT CHICAGO O'HARE CAUSED ME TO OVERESTIMATE THE VFR SVC ACTUALLY RECEIVED FROM DEP CTL. I DID NOT EXPECT DEP TO RELEASE THE ACFT UNTIL IT WAS OUT OF THE CHICAGO/MIDWAY AREA. I ALSO FEEL THAT I DID NOT DO SUFFICIENT FLT PLANNING IN THIS REGARD AND CONSIDER MYSELF NAIVE IN REGARD TO BOTH THE SVC EXPECTED AND THE ABILITY TO OPERATE SAFELY IN SUCH COMPLICATED AIRSPACE WITHOUT MORE PREPARATION. WITH REGARD TO THE MINIMUM ALT CLRNC; I FELT THAT I WAS BOXED IN BY CLASS B ABOVE AND THE CONGESTED AREA BELOW. THE SAFEST THING TO DO WOULD HAVE BEEN FOR O'HARE DEP TO KEEP US AT A HIGHER ALT AND STAY WITH US UNTIL WE WERE OUT FROM UNDER ALL CLASS B AND SAFELY AWAY FROM THE MIDWAY CLASS C. HOW IT/THEY WERE DISCOVERED: I IMMEDIATELY REALIZED THE POTENTIAL AIRSPACE AND MSA COMPROMISES BASED ON MY KNOWLEDGE OF FAA REGS. WHAT I LACKED WAS TIME TO ADEQUATELY CONSIDER OPTIONS. DUE TO THE CONSIDERATIONS OF THE FLT; THE NIGHT THING SORT OF CREPT UP WITHOUT IT BEING RECOGNIZED. CORRECTIVE ACTIONS: IN THE FUTURE; I WILL DO MORE FLT PLANNING WHEN FLYING VFR IN SUCH COMPLICATED AIRSPACE. I WILL NOT TAKE ATC DEP SVC FOR GRANTED AND MAY EVEN CALL THE RADAR CTLRS BEFORE DEP TO FIND OUT WHAT SVC I CAN EXPECT. I WILL REFUSE TO DO SUCH A FLT ON SHORT NOTICE IF ADEQUATE FLT PLANNING CANNOT BE CONDUCTED. HUMAN PERFORMANCE CONSIDERATIONS. PERCEPTIONS; JUDGEMENTS; DECISIONS: I FEEL THAT I USED POOR JUDGEMENT IN MAKING THIS TRIP TO O'HARE ON SHORT NOTICE AND IN DECIDING IN FAVOR OF THE IMPULSE REQUEST OF THE STUDENT TO CHANGE THE DEST FROM MIDWAY TO O'HARE AND ON NOT INSISTING ON MORE TIME FOR FLT PLANNING. I ALSO FEEL THAT THE O'HARE CTLRS; WHO ARE DECIDEDLY BUSY; USED UNNECESSARY ABRUPTNESS IN DEALING WITH THE CREW ON THIS FLT. ACTIONS AND INACTIONS: I FEEL THE ACTIONS OF ATC IN ABBREVIATING THE DEP SVC AND THE LACK OF ADEQUATE PREPARATION ON THE PART OF MYSELF IN PREPARATION FOR THE FLT INTO THIS COMPLICATED AIRSPACE REGION LED TO THE POSSIBLE COMPROMISES. FACTORS AFFECTING THE QUALITY OF HUMAN PERFORMANCE: THE HIGH WORKLOAD OF THE DEP CTLRS AND MY SENSE OF BEING RUSHED; AND INADEQUATE FLT PLANNING ON THE PART OF THE CFI.