The next image is of the two boys proudly wearing their Civil War era hats. During this time period the Civil War was having its Centenniel and the country went a little Civil War mad.
The next two images are from the streets on Old New York. I like the one with the small China Town in the background. Chicago was right next to Old New York where the train station was located which is in the background. I will show the menu from the steak restaurant shown in the top image.