Wine pairing w/contemp american
I know Oceanique, in Evanston, offers a wine pairing along with their tasting menu (although I generally order a la carte when I go there). Their food is contemporary American, with an emphasis on seafood; they also do a great job with soups, sauces, and desserts.
Other than that, I don't know of any place other than the high-end expensive places. But any restaurant can create wine pairings for you. Obviously, those with a knowledgeable sommelier and/or an emphasis on wine may be better equipped to come up with appropriate pairings. For example, the Stained Glass, also in Evanston, is a wine bar (32 wines available by the glass) with very good contemporary American food. And really, any of our better contemporary American restaurants, such as Perennial Virant, North Pond, and Boka, should all be able to deliver good pairings upon request. So should our better Italian restaurants (e.g. Piccolo Sogno), French bistros (La Sardine), etc. They just don't have them pre-selected, that's all.
1729 North Halsted, Chicago, IL 60614
2610 North Cannon Drive, Chicago, IL 60614
1800 N Lincoln, Chicago, IL 60614
505 Main St, Evanston, IL 60202
464 N Halsted, Chicago, IL 60622
The Stained Glass
1735 Benson Avenue, Evanston, IL 60201