There is information about the Free Sewing Machine Company on the following link.
The Free Sewing Machine Company I haven't found information about them being manufactured in Chicago, but that they were manufactured in Rockford, IL. Although, it's possible that some parts for them may have been made in Chicago.
Is this sewing machine something that has been in your family for a long time? It's really hard to put some kind of monetary value on your machine without seeing it and knowing the condition of it.
Whether it has much monetary value depends on its condition, functionality, beauty and what someone would want to pay for it. However, what something is worth sentimentally can be priceless.
You could do a search on eBay and see if there are any like yours for sale. That might give you an idea as far as possible prices for it.
A lot of people will say that the old machines don't have much value either monetarily or even sentimentally, because they keep appearing in yard and garage sales, etc.
However, some of the machines from the early era of them can be quite beautiful in the artwork on the machines themselves and also in the cabinetry work. Also, if the machine actually works or could be made to work, then that is an added plus!
They can make a nice display in the home if you get creative and put some things around them that are also from the same era from when they were made. They can become great conversation pieces then.
In my home, almost every piece of furniture has a story behind it. Either having a long history in my family or, there was an unusual way in which I acquired them.
Just a tip. If the machine is on a stand that is made of cast iron, which either all or part of it almost certainly is, please be very careful when moving it so that it doesn't get dropped. The cast iron does break very easily. That's how we lost a very old family sewing machine. I was the one who dropped it on the cement outdoors!
Someone who commented on an earlier post I made about the "value" of an old sewing machine added the following:
I sold a 1883 Singer sewing machine, with a Coffin top, that covered the machine on top, instead of it dropping down into the cabinet, for 530.00. It was in very good condition, with 6 side drawers. Hope this helps, bhfinds.
But, nonetheless, we do find old sewing machines being given away and selling for just a few dollars that may actually be in overall great condition. It all depends on a lot of factors.