Anniversary Dinner Downtown
I am coming home! Yay! Haven't lived in Il for 14 years, but born and raised and miss the food! Will be coming home, staying in Chicago for 1 night only :(, next week. Want to take husband out for 5th anniversary dinner. We are staying at the Hyatt on St. Clair, but distance is not a factor (I love to take him in the scary cabs)! We love all kinds of food, Polish, sushi, steak, etc. Price, want to keep it moderate (around $100 for two). Looking for romantic obviously, but does not need to be over the top.
The standard answer to this one is North Pond.
But if you want to be more adventurous, I would suggest Sol de Mexico. Unlike so many of our better restaurants, you will likely not have to sit elbow-to-elbow with other customers. The mole dishes are excellent, and the service is discreet and friendly.
While North Pond is indeed romantic and the food excellent, it will run about double your target price. Check the website menus for this and other places for pricing.
I would not recommend Sol de Mexico. It is extremely inconvenient geographically, and I've found the food only so-so. You can find far better Mexican food much closer to downtown. If you want to go that route, I recommend Salpicon, Mexique, or Mundial Cocina Mestiza.
Also close to the Hyatt and excellent are a couple of other anniversary-worthy restaurants: Piccolo Sogno Due (Italian), and Sable (contemporary American small plates, craft cocktails).
All of these accept reservations on Opentable.com so you can tell at a glance which ones have availability at your desired date/time, and all are moderately priced and should fit your budget or pretty close to it.
If a short cab ride is not a problem, the West Loop is doing great food right now.. a longer walk would be River North
Anniversary worthy for your price point I would rec: Nellcotte (West loop), Balena (Lincoln Park), Perennial Virant (lincoln park), Vera (west loop) would be a bit more casual, Nightwood in Pilsen may run upper limit of budget.
Second the Piccolo, but the original would be more consistent on Grande (Piccolo Sogno).
>> Second the Piccolo, but the original would be more consistent on Grande (Piccolo Sogno).
I'm not sure what you mean by more consistent. I thought Piccolo Sogno Due was a very similar (virtually identical) experience to Piccolo Sogno at Grand/Milwaukee/Halsted - great Italian food, amazing bread service, incredibly knowledgeable and helpful servers, spacious seating, available outdoor seating (weather permitting), moderate noise level, and did I mention the great Italian food? Even down to Ciro greeting folks at the door. About the only significant difference I noticed, aside from the location (which is more convenient to the OP's hotel), is that Due has more of an emphasis on seafood in the menu selections. Although even a non-seafood lover would be happy at either one.