First time in Chicago/Westchester
I'll be going to the Chicago area next week for work and our hotel is in Westchester. We'll have a company car and will have the evenings free. I've heard the food in Chicago is amazing. I'd like fine dining or something unique to Chicago. I love all types of food, but mostly I enjoy an interesting and tabletop. I'm from Dallas. What can I not miss? Is parking an issue in the city? Thank you!
Westchester is about 15 miles from downtown Chicago. If you'd like to eat closer to your hotel, you might search the Board for "Western Suburbs" or "Oak Brook" for some ideas. Among places reasonably close to Westchester that I would recommend are Emilio's Tapas in Hillside and Greek Islands in Lombard. Also, for fine dining, you might try Vie in Western Springs. Parking at all of these places (as in most of the suburbs) is free.
Parking in downtown Chicago and in the more upscale neighborhoods of Chicago is not an issue so long as you are prepared to pay for it. Free parking downtown is virtually nonexistent and even metered spaces are few. Many restaurants have valet parking, and lots are plentiful generally.
You might want to give us more insights into your food preferences. "Unique" Chicago cuisine include deep dish pizza and Italian beef.