I'd guess 1903 - 04, really good mid size car Packard or Winton. The rear entrance door was a popular style back then, when chassis got longer there was room for side doors. Merry Christmas. Here is a 1904 Knox for the view of the rear seating with a rear door. Bob
The popular Santa we know was introduced by CocaCola. The car looks to be a taxi with that roof rack. The coachwork shows signs of older influence, while the splash guards are newer style. Merry Christmas
It seems that 1902 is correct. You can see "1902" (mirrored) in the lower left corner of the image. https://images.chicagohistory.org/asset/276/
Based on? The negative is marked 1902, the (no longer working) link on the Wikipedia page went to the Library of Congress, and the link I posted in #8 has "Chicago Daily News negatives collection, Chicago History Museum." Here's the summary from Wikimedia Commons: I came across the picture and caption on the Wikipedia page on Santa Claus.
Good eye and research. Very interesting. The mystery thickens. I wonder if the picture was published in the newspaper. Someone should contact the Chicago History Museum.
Here's a 1903 Winton! https://cars.bonhams.com/auction/27509/lot/21/1903-winton-2-cylinder-tourer-chassis-no-1718/#photos And here's a 1903 Packard! Man, look at that red paint. The tonneau looks more like it, and it's got one lamp on the left rear, but the front fender is way off. https://www.conceptcarz.com/profile/8558,9994/1903-packard-model-f.aspx
^^^^^^^^^^^^^^ Thanks for taking the time to find and post the photos of the Winton and Packard, think the OP photo matches the Winton. The Packard is close to a sister car that was the first automobile to drive cross country with two men and Bud the Pitbull. Have a Happy New Year! Bob https://www.atlasobscura.com/articl...ry-road-trip-took-2-men-and-a-pitbull-63-days