The Chicago Board of Trade dominates the 1956 skyline.

Today it's barely visible from the same vantage (16th Street).

The clock tower of the Dearborn Station can be seen to the right of the building with the yellow Lee sign painted on the side. If you were traveling by rail to or from Los Angeles, you probably transferred at that station in Chicago. It's where the Atchison, Topeka and Santa Fe began and ended its passenger trips to and from a number of Western cities. The tower is still standing and what is left of the station has been converted to office and retail space. The train shed and tracks were demolished in 1976. The office, printing and manufacturing businesses around it left and the buildings are now mostly apartments and lofts.

That tractor without mudflaps is likely a yard tractor and not used on streets and roads.

Of the two tallest at the time, Prudential was the tallest, hence it being the location of the TV transmission tower. I recall my dad taking my brother and me up to the observation deck on a Sunday morning around this time. I was 6 years old then.

The large building with the pyramidal top is the Board of Trade, and the bright metal, blocky building with the tall antenna is the Prudential Life building. These were the tallest things in the city from about 1955-1965.

So this puts us on the south side, and I'm pretty sure the low bridge visible in the middle distance is the Roosevelt Road bridge over the river. I'm guessing we are near what's now the 18th street bridge where it crosses the south end of today's Metra (commuter) trainyard.

You can see the tower of Chicago Grand Central on the far left of the picture. This curve is just east of the lift bridge over the Chicago River.

There were/are a set of standard viewing locations for photographing Chicago railroading. This isn't one of them, and is thus valuable. It was probably shot from the train.

Chicago experts should be able to fill in the details, and the exact location, but 2 small ones pop up. All of the switches in the foreground have self guarded frogs, a once-common cost saving feature for yards. These are the wings sticking up above rail level on the sides of the frogs, allowing omission of the usual guard rails on the outer "stock" rails, to keep wheels from steering down the wrong side of the frog. They are not suitable for high speed main line operations.

Also, the hood profile of the semi tractor facing us looks like an International (IH), which was based in the general Chicago area. The one facing away lacks mud flaps, was that common for the era?