Prosecutors say a hotel meetup ended with a dispute, a chase from a parking garage and a fatal shot fired into another car.
OAKBROOK TERRACE, Ill. — A 19-year-old Milwaukee woman is being held in DuPage County on first-degree murder charges after prosecutors said she shot 28-year-old Obaidulla F. Shareef in the head after the two met through Tinder and spent time at an Oakbrook Terrace hotel.
The case drew quick attention in the Chicago suburbs and Milwaukee because investigators said it moved across city and state lines within hours. Police say surveillance video, hotel accounts, license plate reader data and follow-up warrants helped identify Akrystal C-Woods after Shareef was found wounded in his car on Feb. 4 near 2 Trans Am Plaza. Since then, Woods has been extradited from Wisconsin, denied pretrial release and ordered to remain in custody while the homicide case moves ahead in DuPage County court.
Police were first called at about 6:06 p.m. Feb. 4 to a report of a vehicle crash in the parking area near 2 Trans Am Plaza, a commercial property near Interstate 88. Officers arrived to find Shareef in the driver’s seat of a car with what authorities described as an apparent gunshot wound to the head. Prosecutors later said the car had exited a parking garage at a high rate of speed, crossed a grassy area and hit a parked vehicle across from the garage. Paramedics tried life-saving measures, but Shareef was pronounced dead at 6:22 p.m. The fatal scene ended a chain of events that, investigators say, began at a nearby Comfort Suites on Roosevelt Road, where Shareef had checked into a room with two women earlier that day.
According to investigators, Shareef had met the women through the dating app Tinder. A witness at the hotel told police that Shareef appeared uneasy before the meetup and said he was nervous about seeing the women in person. Hotel accounts cited by investigators said one of the women, later identified as Woods, accused Shareef during a dispute of taking $200 from her. The argument grew heated enough that Shareef, Woods and the second woman were asked to leave the property, according to the account relayed in court records. Prosecutors later outlined a more detailed sequence, alleging that Shareef had left the hotel at one point, returned the next morning and left again before the women checked out around midday. What happened in the hours between the hotel dispute and the shooting remains only partly public, and authorities have not laid out every step of the group’s movements.
Investigators say the next key stop was the parking garage at 2 Trans Am Plaza, about a mile and a half from the hotel. Prosecutors allege that after the women checked out, they met Shareef there to smoke marijuana. At some point, according to the charging account, Shareef entered Woods’ vehicle. Prosecutors say Woods grabbed Shareef’s cellphone and tried to move money from his Cash App account to herself. They allege Shareef pulled the phone back, got out and returned to his own car. Both vehicles then moved toward the garage exit. Prosecutors say Shareef’s car stopped alongside the passenger side of Woods’ vehicle, and Woods then pulled out a gun, rolled down the front passenger-side window and fired across the face of the person in that front seat, striking Shareef in the head. Authorities have not publicly identified the second woman or the front-seat passenger, and no public filing available in the case has explained whether that person faces any allegation.
Law enforcement officials have pointed to technology and witness work as central pieces of the investigation. Police said they used surveillance footage, social media records and license plate reader information to connect Shareef’s car and a second vehicle carrying Woods and the other woman to the garage and then to Milwaukee. Fox6 reported that investigators linked the second vehicle and the women to an apartment complex near 73rd Street and Dean Road on Milwaukee’s northwest side. Officers executed several warrants there on Feb. 5, one day after the shooting. Woods and a man who was with her were taken into custody after a traffic stop in the suspect vehicle, according to that report. Authorities have not publicly detailed the man’s role, if any, and prosecutors have said only Woods has been charged so far. That leaves open a set of still-unanswered questions about who else may have been present during the final moments and whether additional counts could be sought later.
The formal criminal case began to move quickly. DuPage County authorities said Judge Robert Walsh issued an arrest warrant for Woods on Feb. 7. Prosecutors announced on Feb. 9 that Woods, identified by the county as Akrystal C-Woods of Milwaukee, had been charged with three counts of first-degree murder in Shareef’s death. She was in Wisconsin custody at the time. In Milwaukee court on Feb. 10, Woods waived extradition, clearing the way for Illinois authorities to bring her to DuPage County. She was returned on Feb. 19 and appeared in first appearance court on Feb. 21. That same day, Judge David Schwartz granted the state’s request to deny pretrial release, keeping Woods in jail while the case proceeds. DuPage County State’s Attorney Robert Berlin said the allegations would be met with what he called the full force of the law. Oakbrook Terrace Police Chief Casey Calvello said Woods’ first appearance marked the start of the judicial process and said investigators would continue supporting the prosecution.
The public record so far gives only a partial look at Shareef’s final day, but several details have sharpened the outline. He was 28. He was found alone in the front seat of his car after what police first approached as a crash call. A hotel receipt inside the vehicle helped connect investigators to the earlier meeting. Witnesses at the hotel provided the first account of his unease. Then cameras and license plate readers filled in the movement from the hotel to the garage and from Illinois back to Milwaukee. The setting itself adds to the story’s starkness: a suburban office plaza, a hotel off a busy road, a garage where prosecutors say a dispute over a phone and money turned fatal in daylight. Officials have expressed sympathy for Shareef’s family and friends, but little has been publicly released about his life beyond the facts of the case. No defense narrative had been aired in detail in public statements released by county officials as of mid-March.
The next phase is now centered in DuPage County court. Woods remains charged, but the case is still at an early stage and the accusations have not been tested at trial. Under Illinois procedure, prosecutors will continue turning over evidence, defense lawyers will have a chance to challenge the state’s account and a judge will oversee scheduling for future hearings. County officials said on Feb. 21 that Woods’ next court appearance was set for March 9 before Judge Margaret O’Connell. Public statements released by the county did not immediately describe what happened at that hearing, leaving the latest publicly posted milestone as the denial of pretrial release and the continuing murder prosecution. No additional defendant had been announced, no plea had been entered in the public summaries and no trial date had been listed in the county news releases. For now, the case stands as a homicide prosecution built around hotel witness accounts, digital tracing and a shooting investigators say followed a brief but escalating conflict.