I have 2 sumps in the basement. One for rain/foundation water.
Once when gardening, I found clay drain tile. When there was a sewer issue, they found clay tile by the house for the sewer line.

Does anyone know what type of foundation drain tile they would've used in the Chicago area in 1958 commonly? Clay? or ???
Also, does anyone know how window well drainage was treated at that time? I've dug down a bit (soil/clay with rock) about 10" below the bottom window opening but can't see anything so far. Is looking for a pipe futile? This is VERY hard to dig with the rocks/clay mix so I don't want to be wasting my time. But did I dig down far enough?

Thanks for any help.

Any clay drains I've excavated from that era had shifted, were full of mud and useless. Your window wells were obviously not even connected with any weepers that may have been installed or you would have run into the line. So don't bother looking any further.

And since you know the fixes, I can't add anything.

The pic here shows the proper way to attach window well drains--directly into the weepers. (Later, the foundation membrane will have to be cut and secured to the wall around the window well.)

Translucent window well covers might divert enough water away to alleviate your problem.

Covers won't work because the water is just filling in via the bottom. It's not rained hard enough lately to see if water is seeping in between the house & metal well.

Thought maybe we'd rent an auger or Chipping hammer to hopefully dig down to cleanish gravel and clean the clay/soil out of the top. Thinking if that was done, maybe the water would trickle down.

I take back what I said about my knowledge on fixes :). I do know I don't want to make a hole through the house to have an inside drain. Or - I'd "prefer" not to. Only a 1" pipe would fit between the walls which might be ok, but it would be very tricky to do without tearing apart all the drywall down there.

Why do you think you're going to find gravel further down? If the builder had followed good practice, the well would have had gravel at least two or three feet down from the start.

Excavating the entire foundation, waterproofing it and installing weeping tiles is the surefire cure. But expensive! Or messy and backbreaking if you're doing it yourself.

Instead, you could try excavating several feet deep in the window wells, filling them entirely with loose gravel and perhaps running out a weeper or two into the yard from that level.

I've done that in a couple cases and it was sufficient to solve the problem.

Here's a view of recommended window well installation:

National Research Council of Canada. Basement Guidelines