cincy 2 weeks
You will spend major $$$ at Boca. Slim's is the best in the city IMHO. Service may be slow, but the food is carefully and artistically prepared. They welcome you bringing your own wine and will supply an opener and glasses, no corkage fee. Jean-Ro's downtown is a less pricy incarnation of Jean Robert at Pigall's, and the times we've been, the food has been top-notch. Let us know what is chosen and what you thougt.
Someone will inevitably make the recomendation of Montgomery Ribs. Good restaurant, but lousy ribs. BarbBQ Revue in Madison or Jim Dandy's in Sharonville are far superior.
While I've never been, I hear great things about the Dilly Deli in Mariemont. Live bands at least once a week and good food.
re: JohnE O
I haven't been to Dilly Deli in a few years, but it's not something I'd put on your list unless you're staying in or near Mariemont. (And in that case, I'd recommend The Quarter instead as a splurge). The sandwiches and salads I had at Dilly Deli were good, but I always felt like I was spending a lot for what I got. The value just wasn't there for me. But again, I haven't been there for awhile, so maybe someone else can provide a different perspective. My favorite local place (not as far east as Dilly Deli) is Kona Bistro in Oakley ... a few blocks away from Boca.
For Cincinnati Chili, go with Skyline - easy to find - there is one on almost every corner. Try a 3, 4, or 5 way (your choice depending of whether you like beans/onions) and get a cheese coney on the side.
Graeters is tops for ice cream - make sure to get a flavor w/chips in it. My personal favorites are the mocha chip and the coconut chip. Several locations around town - if you let me know where you are staying I can recommend the closest.
Most of the other "foodie" type restaurants I would recommend are pricey (Boca, Daveeds, Carlo & Johnny's, Pigall's). Primavista is good italian food with a nice view of the city and is a little less expensive. Slims in Northside is fun w/a group and you bring your own liquor/wine, but service is very slow IMO. There is a place at Newport on the Levee (just across the river from Cincinnati in Kentucky) called Istanbul Cafe that has a delicous dish called a turkish gyro.