Sample on Allen near elmwood is great. you order a bunch of $2-$4 menu items, all gourmet type items, and then share. it was a lot of fun. figure on spending about 75 bucks total for 2 people.
tempo on delaware in the city is nice. pricey, but the food is amazing.
hutches on delaware near west delavan is great for fish and steaks.
bacchus on chippewa and franklin is good as well. great wine selection, had a great seared ahi tuna dish last time i was there.
chop house for steaks. hands down. some people will tell you eb greens, but in all honesty, i think the chop house blows eb greens out of the water. the bone in ribeye is to kill for, and pair it with a lobster tail or crab legs, and you are in heaven.