To piggyback on this conversation, I have one day (tomorrow) in Chicago, I'm staying at the W Lakeshore en route to a family event, no car (but cabs are fine), and one night for dinner. And I'm from San Francisco, which I mention only for context. My favorite restaurants tend to the smaller (but cool) places with younger chefs who aren't so popular that it's become a huge production yet (fancy restaurants become a business, and it's hard to keep cooking with love). but I still like Gary Danko in San Francisco (and go to the Mission or Potrero Hill otherwise, if you know the area).
I'm a Shawn McClain fan. You might want to search for the following:
Of course, Schwa would be perfect, but that's a near-impossible reservation nowadays.
Graham Elliot also just opened his new place, and it's quite affordable.
Take a look at Sweets and Savories, too.
There are more detailed explanations on some other posts, but here is the short list of can't misses for Chicago cuisine:
Maiz (cash only, great, authentic Mexican, not expensive. They have huitlacoche -- corn smut, which is apparenlty considered a delicasy in Mexico).
Blackbird (go for lunch and get the porkbelly sandwhich)
Hot Dougs (mentioned elsewhere in this thread)
Schwa (call asap and try to get a reservation. They have a smaller tasting menu if your budget is an issue)
There is a place in China Town that has soup dumpings -- which are apparently very hard to come by: Lao Shanghai
If I wanted a first class experience, I would skip Alinea or Moto and go to Tru (but personally, I am not a huge molecular gastronomy fan and I didn't love Alinea). I also don't care for Everest -- but if you like classic, heavy french food, you will like it. I haven't been to Charlie Trotter's, so I can't speak to that.
soupy dumplings are indeed difficult to come by in Chicagoland area (there are several 'xiao long bao' (minced meat/veggies in those little buns with no soup) places, but that's about it.
with that said, i was drawn to Lao Shanghai because of an article posting on their window (and it was new at the time). However, please DO NOT go there, and definitely DO NOT order the soupy dumplings... the skin's consistency and flavor of the meat shouts out they're the frozen variety picked up at grocery stores to be steamed and served at a restaurant... they are terrible !!!
Knowing what I know. I tend to lean towards the bargain joints that pack a great value:
Sol de Mexico
Possibly Marigold for Indian - since you wanna drink too.
Khan BBQ on Devon (no liquor) (Usmaniya, Chopal, Sabri Nehari for other choices on Devon)
Las Asadas on Western. Lunchtime steak taco or burrito. (I get both!)
Tac Quick on Sheridan (Thai - BYOB)
Lao Sze Chuan in Chinatown
Tore's Beef on Diversey / Western / Elston
These are not the "Top 5 Best Restaurants" but, if I had three days here, knowing what I know, these are places I would try to get to. I didn't mention pizza, cause that's just a "given." I would get thin crust though. I usually only get stuffed pizza when I'm entertaining out of town guests.
If you want top 5 for high end's sake, then this is not your list. If I had a zillion dollars, I would still get to these places if I had three days.
In fact, I am meeting my gourmet/oenophile son in Chicago next week for a three day restaurant visit. We're going to: Topolobampo, Everest, and Custom House (the first and last are open for lunch and dinner). For something less formal (and open almost anytime), we'd go to the Gage (a pub restaurant).
I'll bite. I'd do one super high-end meal and (1) alinea most clearly fits that bill. Second, I'd do some haute-Mexican, probably (2) Sol de Mexico. I'd go to (3) Hot Doug's in this city of dog's homage to the weiner. For a great-value and really enjoyable BYO meal, I'd check out (4) Bonsoiree and do the tasting menu there. I'll include one drink place (5) Whiskey Sky at the top of the Lakeshore W hotel would be it for the lake and navy pier view and the inventive (albeit pretty pricey) drinks.
I read once that there are 40,000 restaurants in the greater Chicago area. Seemed like a high number, but I really would not be suprissed if it were true. That being said, there are a lot of great places to eat in Chicago and it woudl help if you could gie some ore information, such as:
Where will you be staying?
Will you havre a car?
Any budget considerations (higher end meals in Chciago can get up to $700-$800 for two. Is that OK?)
Any preferences? There are all sorts of cuisines available. What sort of food do you like?
And if you mean the annual restaurant show, make reservations soon for any higher end restaurant. Some are probably already booked up for that week.
wak's advice is excellent, as is his request for additional information.
One of the things you will also want to consider is whether and how to balance your meal choices. Do you want to eat three dinners at our top temples of haute cuisine, or would you prefer to vary your choices? Would you prefer ethnic cuisine? What about local specialties? If you really love one or two specific types of food, chances are you can find great examples here, so just ask.
Also, what about different meals? You can have great breakfasts, great lunches, and great dinners, but some places are better for some meals than others. Can you fit three breakfasts, three lunches, and three dinners into your itinerary (and stomach)? Will lighter fare done well - say, hot dogs or tacos - satisfy your palate, or would you prefer more ample, complete (perhaps multi-course) meals? Or will you be busy at the show during the day, so you're only concerned about dinners?
Personally, and knowing what Chicago has to offer, I would have one dinner at one of our top tables (e.g. Alinea), one dinner at one of our best casual fine dining restaurants (e.g. one sixtyblue if I were in the city, Michael in the suburbs), one lunch or dinner of deep-dish pizza (e.g. Giordano's), and one lunch or dinner of provincial Mexican food (e.g. Topolobampo in the city, Flamingo's in the suburbs). But your preferences for types of food might be entirely different. Let us know and we can provide more specific recommendations tailored to your taste.