In January 2024, Bob Levy reached out once more to ANTIQUES ROADSHOW to correct his previous update. In the months since this post was updated, Bob was contacted by Geoffrey Baer, the host and producer of numerous documentaries about Chicago architecture, who informed him that the building Bob used to identify the earliest year the painting could have been painted was not 333 N. Michigan Avenue, as Bob believed. But rather, it was the building next door to it, the Old Republic Building, which was completed in 1924. Therefore, construction on 333 N. Michigan Avenue was not underway at the time the painting was completed, as Bob previously thought.    Bob, Geoffrey Baer, and the team with the Chicago Architecture Center now agree that the painting was completed in 1925. ANTIQUES ROADSHOW will use circa 1925 going forward. Update: 3.21.2023: An ANTIQUES ROADSHOW viewer named Bob Levy got in touch with appraiser Betty Krulik in February 2023 to say that he believes this William Clusmann oil painting of a Chicago street scene, which Krulik estimated as ca. 1910 during her on-air appraisal, may be from several years later in Clusmann’s career than she originally thought.   Bob noted that he happened to be training as a docent with the Chicago Architecture Center and was currently studying several prominent Chicago landmarks, which he said helped him recognize certain buildings depicted in Clusmann’s composition that could date the painting more precisely to the late 1920s.   So with thanks to both Bob and the Chicago Architecture Center, here are details compiled from his very informative emails with ROADSHOW:   “Based on the buildings visible in the painting, we date the painting to 1927. … It appears that the Wrigley Building is visible at the northern end of Michigan Avenue in the painting. The southern section of the Wrigley Building wasn’t completed until 1921 and the northern section, which I believe is visible as well, was completed in 1924. If those buildings are visible in the painting, it’s a bit later than you thought. … “ “What we also see in the painting appears to be 333 N. Michigan Avenue under construction, not yet its full height of 34 stories. Construction on 333 N. Michigan Avenue was underway in 1927 before Clusmann died, and the fact that that building is visible in the painting, and couldn’t have been visible before 1927, is what allows us to date the painting to sometime that year, before Clusmann died on September 28.” Betty Krulik agrees with Bob and the Chicago Architecture Center’s assessment, and ANTIQUES ROADSHOW has corrected the date of the painting to 1927.