Dinner with boyfriend near Magnificent Mile?
Slurping Turtle and Tavernita are options to consider, in addition to those mentioned. Bandera entrees, except for burgers/sandwiches, tend to run in the mid-high 20's. If you do go there, I recommend ordering cornbread as soon as you sit down, and the beef rib entree. Portions are huge so perhaps the option of leftovers for lunch would offset the splurge.
I have some ideas for you, but of course they will depend on exactly where you are:
Bandera is right on Michigan Avenue across the street from Nordstrom at 535 N. Michigan Avenue.
Bin 36, also at the south end of the Mag Mile and a block or two west at Dearborn, is a wine bar with good food.
Bar Toma at the other end of the Mag Mile is a casual Italian restaurant from Tony Montuano who also is the chef at Spiaggia. I've only lunched there, but it definitely had his authentic slow food touch. I would certainly go back.
Another good italian restaurant is Coco Pazzo Cafe, a little east of Michigan Avenue.
Check out the websites and see what appeals to you.
I have to say, I have fortunately never been disappointed in Bandera. Service is professional and the food is very good. They make a decent cocktail if not overly fancy.
The jazz can be a little loud and the window view of Boul Mich does not interest me since I live here, but the room has a nice grown up ambiance which I find very nice...soothing and comforting without being a snooze.
Sable. It's terrific. They serve contemporary American cuisine. Most appetizers are $8-12 and most entrees $16-22; even better, most of the items are available in half portions so you can try a lot of things. I think they keep their food prices unusually low and make most of their money on the alcohol (they have craft cocktails). I've spent under $30/pp on food and left stuffed. And their food is some of the best you'll find anywhere. Don't miss the sweet corn creme brulee, a savory riff on the classic dessert. Advance reservations are recommended. www.sablechicago.com
Sable is in the Hotel Palomar at Illinois and State, three short blocks (0.2 mile) west of the Mag Mile near its south end, and 0.9 mile from the north end of the Mag Mile. If you'd prefer something closer to the north end of the Mag Mile, here are two additional options. Cafe Spiaggia has mid-priced Italian food; pasta dishes are under $20, but other main courses are in the upper twenties. www.spiaggiarestaurant.com And Bistronomic is a good French bistro, where entrees are $19-25. www.bistronomic.net