Just good food.
I will be travelling to Chicago in April to spend my BIG 50 birthday with the girls. We will be eating out frequently, and would like a few recommendations in the $50/person range. We are all pretty adventurous eaters.
We are staying on Randolph near Michigan Ave. Anything within walking distance is ideal, but we will have a car if needed. I have been to Frontera, Topolobampo, Siaggia, Quartrino, Shaw's Crab House, Tattoria No. 10.
What can't be missed?
445 N Clark St., Chicago, IL 60610
Shaw's Crab House
21 East Hubbard St., Chicago, IL 60611
$50/person can mean a lot of things, and can vary depending on quality and quantity of wine/alcohol as well as number of courses and whether it includes tax/tip. Just sayin'. So your best bet to verify prices to see how they fit is by checking the menus on the restaurants' websites. I'll just leave out the megabuck places that definitely will be WAY over your budget.
I'd start with a couple of our contemporary American restaurants. I really love Sable, in the Hotel Palomar, and the food there is very affordable. They offer small as well as regular portion sizes of many of the dishes. I stuffed myself with $30 of food and would order less next time. The chef is Heather Terhune, who ran Atwood Cafe for ten years. Don't miss the sweet corn creme brulee! They also offer artisanal cocktails. The other place in this category is Atwood Cafe; I haven't been there since Chef Terhune's departure, but AFAIK it's still good. The atmosphere is quieter and more luxurious than Sable.
I'd also recommend our Italian places. Three places near your hotel are worthy of consideration. Cibo Matto is in the W hotel a couple of blocks away, and it's excellent. The chef who started it, Todd Stein, recently left to go to the Florentine, another new place within walking distance. And longtime stalwart Vivere is also very good and a few blocks from your hotel.
There are lots more choices when you get further away, but all of these should be within about a ten-minute walk from your hotel. If I had to name one of these as "don't miss" it would be Sable.