I apologize in advance if this is somewhat repetitive of other posts. I sometimes think CH can end up with out-of-towners going to the same 5 or 6 restaurants in cities with many great options, leaving plenty of good meals on the table - but you do the best you can in your limited vacation time.
We were recently in town for a 3 day weekend without our 3 year old - a quick getaway before our second little one comes in April. We toured pretty hard and, by the way, had a great time in your city. While I didn't post a question in anticipation of my trip, I reviewed this board thoroughly and appreciate the many commenters who take time to give advice.
We planned the trip somewhat spur of the moment, so I wasn't able to get reservations at Alinea, Next, etc., but I think we did pretty well anyway.
Friday breakfast - Xoco - fun and relatively inexpensive, for a Bayless place. Churros with chocolate were tasty. I've had better chilaquiles. But a good, quick stop.
Friday lunch - Topolobampo. I wanted to try a Bayless restaurant, and when we were able to score reservations, we snatched them up. I really enjoyed the "aguachile" with octopus starter. So many octopus dishes are tough - this was sliced razor-then and wasn't chewy at all. It actually had great flavor, unlike so many bad octopus nigiri at middle-of-the-road sushi joints. I had an amazing cocktail with chile-infused mezcal, lime, and honey - can't remember the name, but if you see it on the menu, go for it. The smokiness of the mezcal balanced out with the heat of the chile, the acid of the lime, and the sweetness of the honey was great. Main course was the lamb with oaxacan mole. It was good, but didn't blow me out of the water (neither did my wife's ceviche appetizer or stuffed squash blossom entree). The mole was very deep and complex, but the meat and accompanying sides were not that special. Total for lunch for 2 with one drink was over $100 with tax and tip. While I enjoyed it and am glad I tried it, I thought it was too pricey for what it was.
Friday dinner - Naha. Really liked the room and were made very comfortable by our waiter. Wasn't too hungry at this point, so I tried the oyster appetizer - they were very nice and clean. The roast squab with slow cooked bacon, figs, foie gras, lentils, and a red wine sauce was as rich as it sounds and was a nice early Fall dinner. Martinez cocktail was a first for me - the carpano antica formula vermouth sort of overwhelmed the gin; I might try it at home with a less powerful vermouth. Still, based primarily on the squab and some bites of my wife's dishes, this was one of the better meals I've eaten in a long time.
(By the way, it was just a coincidence that all 3 of our meals this day were at the same intersection in River North - but what a neighborhood !)
Saturday breakfast - Do-Rite Donuts in the loop, just down the street from our hotel. These are amazing, especialy the pistachio with meyer lemon glaze. Went back for breakfast on Monday as well.
Saturday lunch was, of necessity, a hot dog with everything from a stand outside the Field Museum. It was actually really good - and the price was right. Can't remember the name, but it was on the Soldier Field side of the museum.
Saturday dinner at Publican - very enjoyable. Beer list is very well thought out, and server was very helpful in choosing. I'm from Memphis and we know pork pretty well here, too, but the country rib, in particular, really stood out.
Sunday lunch - pizza at Giordano's in River North, near Michigan Avenue. We picked this because we happend by it on our way to the Red Line to catch a Sox game, and I remembered it from trips to Chicago as a kid. It was ok. Not my favorite pizza ever, but pizza of some sort is probably a must-do in Chicago. Next time I'd try somewhere else.
Sunday dinner was the Purple Pig. Arrived about 6:30 and waited about 90 minutes. Given the great weather and the fun atmosphere, no problem at all. By 7 they were telling people an hour and 20 minutes, though. I enjoyed all the small plates - the morcilla sausage was probably my favorite, though everything we ate was good. Our waiter was very friendly and helpful with the wine list, and really didn't seem to care how much (or little) we ordered. There were several infants in strollers - despite the noise level, it seemed to be a fun, casual, and fairly family-friendly place. I'd love to go back and try more of the menu.