Dining with picky eater
We will be in Chicago for wine week in March. We will be looking for a dinner spot that has a good wine list or BYO. The challenge is part of our group would prefer a normal steakhouse type place. Nothing out of the ordinary This is what we are having for lunch. Need a good option for both. Are staying on the Mag Mile
I'm a bit confused. You are having a lunch AND a dinner? And you are looking for an option that would satisfy a picky eater for both meals?
I'd do a steakhouse type place for one meal, and Italian for the other. Both should be acceptable to most picky eaters.
For the steakhouse type place, I would consider Hugo's Frog Bar. Hugo's Frog Bar and Gibson's Steakhouse are side by side, share the same ownership, and share the same kitchen. Hugo's is more seafood oriented but also has steaks the same as Gibson's; Gibson's is steak oriented but also has some seafood. It's easier to get reservations at Hugo's and it's not quite so frantic, so that's why I'd choose Hugo's, but either will work. They are near the north end of the Mag Mile.
One other option is David Burke's Primehouse, near the south end of the Mag Mile. It's one of our very best steakhouses. What makes it suitable is that they have more different types of food in addition to the steaks, and it's a bit more contemporary in style, rather than your classic boisterous "men's club" type steakhouse.
For the Italian place, if you're near the north end of the Mag Mile, I'd do Cafe Spiaggia; if you're closer to the south end, I'd pick Piccolo Sogno Due (or, for a cheaper, more casual meal, Coco Pazzo Cafe).
I'd recommend checking out the menus on their websites to help you decide:
All these places have good wine lists. BYOB is not common at nicer restaurants (e.g. steakhouses) in the downtown Chicago area. If you must BYOB, check ahead with the restaurant regarding their corkage policies; the few that permit outside wines often charge as much as $25-35/bottle for corkage, and typically do not permit any wines that are on their own list.