"So if someone would want to try oysters for the first time in a restaurant (not buy and bring home) what would be the best place to do it in the Chicago area to ensure they were fresh, served correctly, and cost effective?"
Doesn't exist!
I feel the quality of oysters both served and sold in the Midwest, Chicago included, has actually declined in the last decade or so. I don't order them anymore, anywhere in Chicago and don't purchase them anymore in the Midwest. I have tried all the resources and find once in a great while a good batch but mostly they are not bright, plump as they should be. Part of the problem is pricing, as the price has risen all sorts of suppliers have gotten into the game, part of the problem is standards, not many know what a truly fresh oyster is like. I stopped going to Shaw's many years ago after consistently being served dessicated oysters and having to send them back to get palatable ones.
I grew up in Massachusetts and spent part of each summer in Maine. I learned to eat oyster with a dash of lemon as well as little necks and cherrystones, Quahogs were served with a sauce sort of like a Russian dressing or what would be called a simple Remoulade sauce in the South.
I continued the lemon practice when we moved to the Midwest but after an outing at the Davis Street Fish place where they used to have a Special of a dozen cherrystones and a quart of beer served with saltines and Tabasco, I changed and never looked back.
We have changed to little necks and cherrystones because they seem to hold up much better to travel and shipment, are available at H Mart out of a bag if you ask and other sources such as Fresh Farms. For oysters, we order in the Winter from Browne Trading but the cost of overnight is becoming prohibitive.
I certainly like to find a decent retail and restaurant source for oysters but I've been disappointed too many times in the recent decade to try much more.-Dick
"If you go through the hundreds of Acme photos on Yelp it looks like these days the raw oysters come with a little plastic tub of cocktail sauce and some lemon wedges. I'm sure there are always bottles of Tabasco nearby, as at seemingly every restaurant in New Orleans."
I confess I never sit at a table in the Acme but only at the bar where all I see is the oysters being served to you directly onto the bar as you eat them, no plate and a bottle of Tabasco present. Usually if a good customer, you get an extra oyster or two from Hollywood.
One last thought, all shellfish sold and harvested in the US must come with a Harvest Tag delineating, place of harvest, harvest date and shipping date. If your supplier or restaurant can't show you such a tag, I suggest you decline the shellfish.-Dick