The U1chicago Chicago token collection
U1chicago
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Given my username, it would follow that I would be attracted to tokens related to Chicago. So here I present the small subset of my collection now known by the super creative moniker of "U1chicago Chicago token collection" 
The mainstay and the one that started it all is the C.D. Peacock.
There are a few types that I am aware of; this one HT-M23 has a somewhat different look for the Peacock and it's facing in a different direction (as compared to the M19 and M21...see link at bottom for examples of those two).
Heritage has the following blurb about this piece:
"According to Rulau, HT-M23 was struck in 1906 by Gorham Mfg. Co., on order of jeweler Charles Daniel Peacock. A numismatist obviously had a hand in the design of these pieces, which resurrect the motif of the 1837 Smiths Clock Hard Times type."
And CU member Broadstruck offered this tidbit of info:
"Although actually struck circa 1900-1906 these are part of the Hard Times Token series since Lyman Low included them in his 1906 supplement on the series. The 1837 date on the obverse reflects the year of establishment. This is the scarcer earlier variety on which the high relief peacock's breast feathers did not fully strike up. The more commonly encountered HT-M19 was issued later struck from a completely different obverse die featuring a flat peacock design."
Plus some history:
"The House of Peacock first opened its doors on February 9, 1837, the same year Chicago (population 4,000) was incorporated as a city. [...]"
More here:
https://cdpeacock.com/history/
M19:
http://www.usrarecoininvestments.co...n-time-is-money-ngc-au58bn-7230011_6028_d.htm
M21:
https://www.cointalk.com/threads/help-two-cters-work-out-a-token-trade.299621/
Here are the main difference I've noticed:
M19: Peacock is looking to the right, date (1837) is inside the inner circle
M21: Peacock is looking to the right, date (1837) is outside the inner circle
M23: Peacock is looking to the left, date (1837) is outside the inner circle
Also the M23 had different feathers vs M19 & M21 as well as showing the full body of the peacock (vs being cut off on the other two).
Comments
I like toned coins, so this 1892 So Called Dollar (HK-160 / Eglit-97, R.4) is a bit of a jab against that given that the token advertises one of the benefit of aluminum being no tarnish. I'm also a fan of the Columbian Expo Commemoratives, so that is another thing that drew me in.
An example can also be found here:
https://www.so-calleddollars.com/Events/Worlds_Columbian_Expo.html
The most recent addition (as well as the photos) is courtesy of @coinsarefun
This particular example is from Freeport, IL but the company has Chicago ties (so it counts in my book).
Prima Beer was a lager brewed in Chicago. One source linked below quotes the start date as 1890 but as can be seen on the token, the date is 1894. Which is correct? I'm not quite sure as of this point.
Prior to Prohibition, Prima was the largest brewery in Chicago. They continued operations during that period as one of only seven authorized companies; one of their products was a non-alcoholic beverage called "Primalt." By 1941 they merged with Bismarck Brewing. Manhattan Brewing Company of Chicago, which had associations with Al Capone and organized crime, owned stock in the Prima-Bismarck Brewing Company.
As can be seen on the token, Prima’s slogan was “America’s Finest Beer.” As far as I can tell, Chas. D. Franz was the Prima distributor in Freeport.
This token is available with multiple different cities and slightly different reverse designs. Besides Freeport (Illinois), I've seen cities in Iowa, Wisconsin, Missouri, Colorado, and Illinois. There is also a version with FDR in place of the woman and "America" in place of a city name.
Sources/more info (note: some of the info doesn't quite match):
https://explore.chicagocollections.org/marcxml/chicagohistory/30/542k345/
https://www.chicagonow.com/look-back-chicago/2013/04/prima-beer-lingers-on/#image/1
https://en.numista.com/catalogue/index.php?r=Prima Brewing Company&ct=exonumia
Will there be any more? Hopefully so! And they will go here.
Great peacock!
Never thought I’d say it but that peacock has a particularly pleasing patina. Cool mini set, too. ⭐️
Nice tokens.... I like the first one with the Peacock and 'Time is Money' slogan. Cheers, RickO
The Peacock is definitely my favorite!
I figured you might also like the message on the second example.
Being in NW Indiana I've seen some fantastic collections of Chicago tokens over the years.
I never got very far with my own but I do have some including a coupe Peacock tokens in other token collections. I see a lot of these around here but they're usually pricey and even common good fors bring few dollars.
From what I have seen, the Peacock Token is increasing in price the last few years. I've wanted to pick up the other versions but haven't had much luck due to these higher prices. My example was a bargain at slightly over $100. Lately I've seen raw example with problems sell for quite a bit more than that. And the graded examples tend to have spirited bidding on all the major venues (eBay, Stacks, GC, etc).