Moving around a wine list is just like shopping in the grocery- get to know the products and the market. I can tell anyone how much a can of beans or dozen eggs usually costs me. Just a casual walk through wine aisles every time you shop can get you familiar with wines and producers. Once you get to know the market you will notice many Chicago restaurants charge 250-400 percent of retail, though they pay wholesale. That means a bottle which costs you $10 in the store will cost you $25-40 in a restaurant. Wine lists are constructed to get the most money out of lower-end wines and a lower markup from higher-end ones. Even then you may be paying $225 for a wine which retails at $100. Plus by the glass prices are the biggest ripoff- most restaurants try to get close to retail price out of each glass!
Now I'm not saying restaurants should'nt make money vending wine. After all, they do provide all equipment, storage, training, glassware, etc. as well as some great food to go along with it. But the prices are excessive and their biggest source of revenue and profit. It is OK to pay the price but better (and more fun) to find deals.
Some restaurants will be offering wines at lower prices than usual markup. This could be due to the restaurant wanting to eliminate inventory in order to sell a slow moving product or wanting to replace it for another. When you know the market and find one of these you will enjoy it twice as much!
Look over the entire list. You may find a varietal from an unusual place such as Sauvignon Blanc from Chile or an unusual varietal from a well known area, ie. Pinot Meunier from Carneros. These wines could be the bargains. Also check out restaurants which allow outside wine for a corkage fee but watch out- if they are charging $25 or more it is too much! You can take that same $25 or more and apply it to one of their wines. Also get a list of great BYOBs near your home. You can enjoy their great food with your wine. Some great BYOBs in the South Loop include Ma & I, Trattoria Caterina, and South Coast.
Have a great meal and good shopping!
(Image courtesy of Flickr)