Mdw tower and C90 TRACON controller reported that an aircraft departed mdw and was instructed to tur...

Narrative:

Aircraft X was issued takeoff clearance with a right turn to 090 degrees. The pilot read back those exact instructions. Upon seeing the aircraft still on runway heading; not commencing the right turn; I repeated the 090 heading and told the pilot to contact departure control. The pilot read back my clearance verbatim. After a few go-arounds; I received a call from departure control to transfer communications of aircraft X. I knew I did; but tried again to no avail. I called back departure control and told them that I could not raise aircraft X. Aircraft X was east bound; but far enough to the north that they may have infringed on airspace protecting the willis and hancock towers downtown chicago. I was informed later in my shift that aircraft X may have had an airspace/obstruction violation. It appeared that aircraft X had not initiated the right turn when instructed.the only recommendation that I have is that pilots comply with ATC clearances when they are issued. If they are unable to do so; advise. If aircraft X needed more altitude or time for the turn; the pilot needed to inform me. I issued the turn when I did because I knew that aircraft would be clear of that obstruction airspace. Even when I re-issued the turn I was confident the aircraft would have been clear of the airspace. Instead; the pilot turned when they desired and left the frequency; not switching to the assigned frequency causing confusion.

Original NASA ASRS Text

Title: MDW Tower and C90 TRACON Controller reported that an aircraft departed MDW and was instructed to turn and contact Departure. Aircraft did not turn and was not on either frequency.

Narrative: Aircraft X was issued takeoff clearance with a right turn to 090 degrees. The pilot read back those exact instructions. Upon seeing the aircraft still on runway heading; not commencing the right turn; I repeated the 090 heading and told the pilot to contact departure control. The pilot read back my clearance verbatim. After a few go-arounds; I received a call from departure control to transfer communications of Aircraft X. I knew I did; but tried again to no avail. I called back departure control and told them that I could not raise Aircraft X. Aircraft X was east bound; but far enough to the north that they may have infringed on airspace protecting the Willis and Hancock Towers downtown Chicago. I was informed later in my shift that Aircraft X may have had an airspace/obstruction violation. It appeared that Aircraft X had not initiated the right turn when instructed.The only recommendation that I have is that Pilots comply with ATC clearances when they are issued. If they are unable to do so; advise. If Aircraft X needed more altitude or time for the turn; the pilot needed to inform me. I issued the turn when I did because I knew that aircraft would be clear of that obstruction airspace. Even when I re-issued the turn I was confident the aircraft would have been clear of the airspace. Instead; the pilot turned when they desired and left the frequency; not switching to the assigned frequency causing confusion.

Data retrieved from NASA's ASRS site and automatically converted to unabbreviated mixed upper/lowercase text. This report is for informational purposes with no guarantee of accuracy. See NASA's ASRS site for official report.

Attributes
ACN	1435478
Time
Date	201703
Local Time Of Day	1801-2400
Place
Locale Reference	MDW.Airport
State Reference	IL
Aircraft 1
Make Model Name	Light Transport Low Wing 2 Turbojet Eng
Flight Phase	Initial Climb
Route In Use	Vectors
Flight Plan	IFR
Person 1
Function	Local
Qualification	Air Traffic Control Fully Certified
Person 2
Function	Departure
Qualification	Air Traffic Control Developmental
Events
Anomaly	Airspace Violation All Types Deviation - Procedural Clearance Deviation - Track / Heading All Types Inflight Event / Encounter CFTT / CFIT

Mdw tower and C90 TRACON controller reported that an aircraft departed mdw and was instructed to turn and contact departure. Aircraft did not turn and was not on either frequency.