Contemp. American, Sat. Night, Mid-End
There are 4 of us that are transplants from Memphis and we've lived in Chicago for 4 years. We like to try new places for dinner when we get together, but it can be overwhelming. I'm usually in charge of making reservations and, when I start looking around on these boards, I get lost for hours.
So, can we have some suggestions? We want to make reservations for 4 for Saturday night. We'd like to have unique, Contemporary American cuisine at a mid-end place. We're 20-somethings and would like a place that is cool, semi-casual and where we'd be able to hang around for a few drinks. Also, we'd like to be able to wear nice jeans. Location isn't a huge deal, but something in the Loop would be easiest.
Here are four places in the Loop that meet all your criteria:
Atwood Cafe faces big picture windows on the sidewalk and street outside, and has the atmosphere of a classy hotel restaurant (which it is, in the Hotel Burnham). Park Grill is at the entrance to Millennium Park and the atmosphere is more like a busy, lively bistro. Rhapsody is in between those two in terms of "liveliness". I've enjoyed eating at all three, with good food and service and nice atmosphere, and yes, all are places where you could wear nice jeans and dally over drinks. I haven't been to South Water Kitchen yet, and more so than the others, its menu leans more towards traditional American rather than contemporary American. Rhapsody is a bit more expensive, with entree prices in the upper twenties, whereas they're in the very low twenties at the other three. You can see the menus (with prices) for all four on their websites.
For a Saturday night, reservations are essential. If this is for tomorrow evening, I suggest you make a reservation immediately. All four of these places accept reservations on opentable.com (and all currently have openings for tomorrow night).