The Angry Crab: These folks have a location up north of Lincoln Square as well as a new joint in Wicker Park, plenty walkable from Ray's. They opened to huge crowds at the Wicker Park spot; Angry Crab had a cult following even when it was tucked way up beyond where the Damen bus stops running, and now that it's in the center of the neighborhood, they are shelling seafood like nobody's business. Check it out at 1308 N Milwaukee Ave.
Sink/Swim: This place is nestled in a row of bars frequented by industry folk (Scofflaw, Best Intentions, Go Tavern and liquors) and as such, remains pretty steady throughout the week, especially during $1 oyster happy hour ( everyday from 9-11pm). And in their own words "although our main focus is fishes, we offer a wide range of dishes". Something for everyone. It's got sleek decor and professional staff, but I've gone there in sweatpants and not been kicked out.
Honorable Mention: Parson's Chicken and Fish, but we've written about this place so many times that it just feels redundant to mention it for seafood as well as fried chicken, outdoor bars, winter bars, bars with games, bars with sports, hipster bars, and whatever else we've included it in.
Hugos Frog Bar and Fish House: Always busy, but for good reason. (They have a location on the Near North Side, as well as Naperville, if seafood and suburban strip malls strike you as a good combo)
Shaw's Crab House: Again, one location downtown, and one in the burbs, who knew this was a thing? They offer both a traditional white tablecloth seafood restaurant experience, and a more casual bar atmosphere. So maybe just wait until your date shows up and decide which direction to go. Be SPONTANEOUS. but also, make a reservation.
There are plenty more places to get your fish on, but we aren't huge fans of pointing people towards something inside of a mall downtown, or within sight of a Cheesecake Factory, so some Magnificent Mile staples have been left out of the list.