RE: Chicago to Lexington, KY
Welcome to Kentucky in January. This Web site has 10 reviews for Kentucky roadfood destinations. I would start there and read all 10.
It would be nice if you had Jane and Michael's most recent dining guides, Roadfood or Eating Your Way Across the U.S.A.
If you don't want to buy the books (good discounts on Amazon.com), you have time to obtain them from your library.
Fortunately, you can enter Kentucky at Owensboro and enjoy the only Kentucky barbeque worth talking about - Western Kentucky Barbeque. Treat yourself to the famous Moonlite buffett (see photos here on Roadfood) for a fun, all-around bbq experience at a well regarded place that still cooks over hardwood coals.
Then you can visit the Homemade Ice Cream and Pie Kitchen in Louisville for apple sauce cake, dutch apple pie with caramel, lemon chess pie, red velvet cake, etc.
If you don't want to detour into Louisville, you can have both a fine lunch and our favorite pies - Chess and Derby - at Claudia Sanders Dinner House in Shelbyville (an easy on and off from I 64). Between there and Lexington is The Glitz, a promising destination according to the new review, but a place I'm not familiar with.
In my opinion Lexington and Central Kentucky are a barbeque barrens, however, the usual bbq chains are here. Owensboro may be a little out of your way, but you'd enjoy it immensely if you're on the bbq trail.
An English tea afternoon at Perryville's Elmswood Inn would definitely sate your desire for desserts and you'd have a nice time, especially if you go with friends or family. I can always recommend dinner at my favorite Kentucky dining room, the Beaumont Inn in nearby Harrodsburg. They cure and serve the best country ham in the region. Reservations needed.
If you haven't been, consider Shakertown Village for a visit and a meal. An overnight there is very nice. Or drive down for the fine Saturday morning breakfast buffet. Reservations necessary.
My favorite restaurant in Lexington is Asian Wind, a Chinese restaurant with a considerable menu of dishes from other Pacific Rim nations.
Lexington has many good restaurants, but I can't give you a name that qualifies in my mind as a roadfood type destination. For an upscale meat and three, visit the Merrick Inn, which is always good. deSha's is another nice place good for Kentucky food.
For fun and hearty, comfort food meals, Ramsey's Diner may interest you. Go to the one near the University on Woodland Avenue. There's a great pie shop next door and Ramsey's serves those pies on its menu. I love the butterscotch cream; it's the genuine article and as good as my mom made for our family restaurant.
Eat Hall's beer cheese while here (you can buy it about everywhere, including Kroger stores). Or just go down to Hall's on the River for catfish dinners and the beer cheese appetizer. You may also want to sample an Ale 8 1, the popular local giner ale beverage bottled in nearby Winchester. And do try our delicious bourbon ball candy.
Finally, the best independent bookstore in America blesses our city. Joseph-Beth is one of the places we take our guests. They then stay an extra day so they can return for a whole afternoon.