Chicago/ Crime & Emergencies

Two Men Robbed at Gunpoint in West Loop, River North Hours Apart Before Dawn

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Published on September 05, 2026
Two Men Robbed at Gunpoint in West Loop, River North Hours Apart Before DawnSource: Unsplash/Michael Förtsch

A 28-year-old man leaving a business in the 600 block of West Van Buren Street was robbed at gunpoint around 1:20 a.m. Friday, and about 90 minutes later, a 26-year-old man standing outside in the 400 block of North LaSalle Drive in River North was robbed by four suspects who kicked him and implied they had a weapon. No injuries were reported in either case, and Chicago police say Area Three detectives are now investigating both robberies.

In the West Loop robbery, a white sedan carrying four suspects pulled up near the victim, and one of the men got out, pulled a gun, and demanded his belongings, according to ABC7 Chicago. The victim complied, and the suspects then drove west on Van Buren Street. Roughly 90 minutes later and about four miles away, four suspects approached the second victim outside in River North, demanded his belongings, kicked him, and implied a weapon was involved before he too complied; the group then got into a silver sedan and drove north, per the same report.

A Familiar Playbook in River North

The 400 block of North LaSalle Street, where Friday's second robbery took place, has a grim recent history. In June, a 32-year-old man was shot multiple times and critically wounded on the same block during an early-morning armed robbery after four men approached him in a vehicle, according to CWB Chicago. That same outlet has also reported that a December 2025 mass shooting in a parking lot on that block involved four gunmen firing at least 50 rounds, killing one person and critically injuring three others.

The use of a silver sedan and a four-person crew also echoes a February incident Hoodline reported on, in which four suspects in a silver sedan rear-ended a car at East Ontario and Rush Street in River North just before 4 a.m., robbed the two occupants at gunpoint, and fired a shot into the ground before fleeing — detailed in our earlier report, River North Rear-End Ruse. Whether Friday's silver sedan crew is connected to that earlier case, or to the white sedan used in the West Loop robbery, remains an open question that has not been publicly addressed by investigators.

West Loop Corridor's Own Robbery History

The 600 block of West Van Buren Street is no stranger to organized robbery activity either. The corridor was included in a Chicago Police Department community alert back in July 2023 after being targeted during a widespread series of armed robberies across the West Loop and adjacent areas, as reported at the time by CBS Chicago. Law enforcement warned in late July that spree-style robbery crews have been operating during pre-dawn hours across Chicago, typically involving small groups of masked suspects using getaway vehicles to target pedestrians on sidewalks, according to CWB Chicago.

Broader Crime Trends and Local Response

Despite Friday's cluster of violence, the wider numbers tell a somewhat different story. Chicago Police Department public safety reports show Area Three's year-to-date reported robberies fell 26 percent through early August, dropping from 888 incidents in the same period of 2025 to 655 this year. Still, the 18th Police District Council, which oversees River North, established a specialized Robbery and Retail Theft Task Force in 2026 aimed at addressing pre-dawn violent property crimes through multi-agency coordination, citing concerns over low clearance rates and repeat offender patterns.

Federal authorities have also taken an interest in Chicago's organized robbery crews. A federal jury convicted three men in July in connection with 14 violent armed robberies of Chicago businesses and patrons, including hold-ups on the North and West sides where automatic firearms were fired, per CWB Chicago. Separately, Hoodline reported last month that Chicago police arrested a 33-year-old parolee with prior aggravated robbery convictions in River North after recovering a switch-equipped fully automatic pistol from an alley dumpster, in our story Parolee Tossing Machine Gun.

Legal Stakes if Suspects Are Caught

Should suspects eventually be identified and charged in either robbery, Illinois law treats armed robbery involving a firearm as a Class X felony under 720 ILCS 5/18-2, carrying a mandatory sentence of 6 to 30 years in prison plus an automatic 15-year firearm enhancement, with no possibility of probation, according to the Law Office of Clyde Guilamo. For now, no arrests have been announced in either the West Loop or River North case, and Area Three detectives continue investigating both robberies as Chicago police work to determine whether the two are connected.