I recently spent a few days in Chicago, and since I got the majority of my restaurant recommendations from this forum I wanted to report back.
My first night I went alone to Café Spiaggia. After initially telling me it would be about a 15-20 minute wait (totally understandable, considering I walked in at about 7pm with no reservation) they managed to find me a table almost immediately. My waiter was extremely friendly and helpful, suggesting a wine that I was a big fan of (although one that I can't remember the name of). I ordered the bucatini and was a little disappointed with it. Some bites were definitely undercooked, although others seemed fine. It was also quite salty, almost unpleasantly so. For dessert I had the bombolini with peach puree, which were outstanding - soft and fluffy and melting, liberally coated in vanilla sugar, perfectly matched with the peaches. It was quite a large order with 5 golf-ball sized donuts, would have been good to share. As it was I ate 4 and then decided to show a bit of restraint. The bombolini were so good I'd be willing to assume the bucatini was just an off night and go back.
For lunch I went to Xoco twice, once alone and once with my husband. The format of the restaurant makes it so that going alone isn't awkward at all - I was perfectly happy with my book and my counter seat. The first time I had chips and salsa which were outstanding, great crunch and salt and the freshness of the salsas. I followed that with the wood roasted chicken pozole caldo which was also delicious, highlighted with crunch from (I think) cabbage and radish combining with the smokiness of the broth. I also had the agua del dia, which that day was melon, lemon and mint, and it was delicious, tart and fresh and packed full of flavour. The next time (actually the next day) we had more chips and salsa. I had the limeade which was very good but very limey (not a problem for me but my husband wasn't a fan). I had the carnitas caldo - it was good but not great, I found the carnitas a little bland and thought they could have benefitted from a heartier broth. My husband had the red chili shortrib caldo and it was WONDERFUL - I stole more than a few bites. The broth made the dish - rich and spicy and a huge amount of depth. Actually at the end we put the rest of my pork into his leftover broth and enjoyed that more. Despite going twice in two days I would have gone back a third time if we'd had time.
That night we had reservations at the Aviary. I was a little anxious as I wasn't totally sure what to expect. We walked in and were shown to our table - we had reservations at 8pm on a Friday and it was surprisingly only about half-full. We decided on the prix-fixe menu although now I can't remember what half the drinks were. For the first round I had the Celery which was delicious, sweet and sound and weirdly reminiscent of celery without being offputting, and my husband had…something else, apparently not terribly memorable except that it was bottled in house and served in a glass bottle with a brown paper bag, which made us laugh. For the second round I had the margarita and his was called Bitters. Again he won on presentation, with his being served on a charred piece of wood with the glass inverted to collect the smoke, and then the rest of the drink being poured in tableside. I think the idea of the drink was that the four different alcohols together tasted like bourbon. Neither of us are bourbon drinkers but the drink was definitely interesting, and the smoke really did add something. The margarita was very good also, served with chili ice cubes so that the longer it sat the spicier it got. By the end it was pretty hot. The last round was the winner for both of us, with my husband having Sweet Corn which was wonderful - the sweet corn foam especially was incredible, smelling just like corn on the cob. I had Horchata which was just unbelieveably good and I resented having to share it with him. To eat we pretty much tasted everything on the menu (actually we literally tasted everything except the Foie Gras bite). We started with the chips which were fun and interesting - obviously some were more successful than others but overall they were quite good. Then we moved on to bites, with standouts being Scallop, Potato, and Tomato (the potato was so good that for our second round my husband had to try it, and I ordered it again). We finished up with Lollipops, which was a perfect ending with the frozen banana being the clear standout. We left a little drunk and extremely happy.
Then we promptly went to Lou Malnati's for pizza because three drinks and about 10 bites of food each did not seem like a good idea. This was my first deep dish Chicago pizza and…meh, frankly. Although to be fair I'm not a huge fan of pizza in general and much prefer thin crust. It was perfectly good pizza but I wasn't blown away.
The next day we went to the Purple Pig for lunch. I thought we'd be clever and show up at about 1:30, assuming the lunch rush would have passed. Apparently the lunch rush never passes. We got a table in about half an hour and were told that usually it would take much longer, but because of the Air Show a lot of the crowds were out at the beach. The time went quickly with their bar service on the benches, so it wasn't a problem. I loved the setup, with the majority of the plates being family style sharing plates. Between the two of us we shared the eggplant parmesan balls, which were delicious and crunchy and cheesy, the meatball sandwich which was good but probably my least favourite of our orders, the chicken thigh kebabs which were outstanding, juicy with a great crisp skin and really elevated by the tzatsiki dipping sauce, and the mortadella, balsamico and pistachio smear, which was amazing. I can't do justice to how good it was but the soft bread and the smoothness of the mortadella with the bite of arugula and balsamic and crunch of the nuts - just incredible. I was sad I had to share with my husband. I'd go back just for this.
For our last dinner we went to Sable. I found the cocktail menu frankly overwhelming and didn't recognize half the ingredients listed, but I highly highly recommend the Transcendental Induction (I think that was the name of it). This is another restaurant where everything is family style, plus they offer half orders of almost all their menu items, which I loved (and used, we ordered half orders of everything except the brulee). We started with the kale chips which were pretty good but I didn't love. Some bites were better than others, and they were pretty oily. Then we had an heirloom tomato salad that was delicious, it seemed to be tossed in garlic oil which added a nice dimension. After that was the chicken and waffles - not terrible, but the chicken was pretty dry, I might have preferred the waffles on their own. Then we had the cherry wood smoked beef brisket, which was very good, and the sweet corn crème brulee, which I'd read about on this website and which was hands down the best thing we ate on the whole trip (in fact my husband said it might be the best thing he'd ever eaten). Fresh corn and a sort of corn custard, topped by the sweet crunchy brulee and a sprinkle of salt, everything worked so well together I was hard pressed not to lick out the bowl. We finished the meal off with sorbet - coconut for him, white peach and cinnamon for me - which was good, but a little icy, and nothing was ever going to live up to the brulee.
So overall, we had a lot of great food on this trip. Can't wait to go back to try some new restaurants (and have some more sweet corn crème brulee).