Kosher in Chicago
Well, if your expecting anything like NYC (where I just returned from), you'll be in for a surprise. The Kosher resources out here aren't as prevalent as most think they'd be. In fact, I'm actually in the process of launching a site dedicated to this topic! :)
Shallots Bistro in Skokie is a great restaurant. Very good food and a nice environment to enjoy dinner in. Their black hat dessert is top notch (having just done a tour of parve molten chocolate cakes during my trip to NYC). Just down the road from them is Zelda's Sweet Shoppe, which has a wonderful assortment of baked goods and cases of great chocolate truffles! Both of these are outside of the city of Chicago itself, but not all too far.
If you feel adventurous, up in the suburbs is Now We're Cookin' Grill, which is one of my long time favorites, with great burgers, ribs and anything else BBQ style. Near there is also Mizrahi Grill which has middle-eastern style food (pita sandwiches, kabobs, etc).
There's the Spertus Cafe in Chicago itself, which I have not been to. It's a collaboration of Wolfgang Puck and Laura Frankel (who used to be at Shallots).
Hope this helps!
Most of the kosher restaurants are in the north - West Rogers Park (north chicgao neighborhood) Skokie and Highland Park but there are now two restaurants in the city that cater primarily to a lunch crowd - Spertus Cafe (http://www.spertus.edu/visiting/cafe_...) and Metro Klub (http://www.centerstagechicago.com/res...) both are very good -
In rogers park there is Taboun Grill (http://taboungrill.com/) IMHO one of the best restaurants in the city - in Skokie you have Shallot's Bistro, Ken's Diner - an excellent burger place, Malibu Pizza next door to kens, Slice of Life and Hy Life Bistro and Srulie's Dleicatessen which is a welcome addition - in HIghland Park there is Now We're Cooking Grill which I also second as have very good food and another hew comer Mizrahi Grill which is a great new addition also in my top 5 restaurants in the chicago land area -
In terms of grocery stores - this will definitely require a trip to skokie or northbrook - there is the Jewel on howard (actually in evanston but right next to west rogers park and skokie), Hungarian Kosher Supermarket and Garden Fress in Northbrook - all three have excellent selections of kosher food and groceries - and in Chicgao there is Romanian Kosher Sausage purveyors of the salamis, hot dogs, corned beef and pastrami amongst other great meats.
for additional reading check out http://tinyurl.com/ChicagoKosherSurvey - below are map linke to my favorite places -
215 Skokie Valley Rd, Highland Park, IL 60035
6339 N California, Chicgao, IL
3353 West Dempster Street, Skokie, IL
I can't add much to the other posts (sad state of affairs in Chicago). Shallots is pricey but good. Taboun is hit-or miss, but mostly good. Ken's makes really good sloppy burgers. Srulie's has good subs & sides (the shnitzel & pastrami -- while not Cardiologist-friendly is a winning combination). I'd avoid Slice of Life - it's not worth a visit.
Romainian (just a meat market) is a dark, dank storefront but they have some excellent sausage products (Italian sausage is outstanding in both flavor and texture). Great garlic dogs (more like polish sausage). The above-mentioned Jewel and even the formerly-competing Hungarian Kosher also carry a selection of Romainian's sausages.
The Jewel in Evanston also has good, albeit pricey, Chinese take-out.