This is admittedly my personal bias on how things should run, but I feel a quality companion will not nickel and dime your time over a taxi ride to/from a fantastic meal. At least, not if she actually values genuine companionship.
In Chicago especially, some of our more interesting dining venues are outside of our main strips in along the Gold Coast/Mag Mile/River North/Streeterville. In fact, those particular areas offer a very limited type of vibe. Most of my dates are visitors from out of town, and it saddens me when I run across someone that's practically been trained to believe I've got a stopwatch running in my purse, because in truth that deficit mentality robs him of getting a peek into the real Chicago, well beyond the same-same hum of the "main strips."
After a first or second date when enough trust has been established, I like to start steering my dinner and clockfree date gentlemen friends into our more diverse neighborhoods, and into those unique spaces and experiences (food, drink, and entertainment) that make our city really shine.
To respond to the OP-I swing all directions.

I greatly enjoy carefully selecting options based on my knowledge and experience of my friend's personality and preferences. Anyone who has shared a meal or longer date with me knows I tend to get a special thrill out of "making their meal" as it were. I also love sitting in the reverse seat-there's something very special about getting to experience a space (dining, entertainment, or otherwise) that is very near and dear to a gentleman friend's heart. And then, for my more adventurous friends who I know can laugh it off with me if the experiment flubs, I really enjoy trying very off the wall places, where we either walk away saying "that was amazing!" or else we have a new horrible, hilarious experience to laugh and bond over.
While top restaurants are always a unique ride, my favorite dining experiences have included an impromptu pub stop in Edinburgh before a concert where I shared my favorite performer with my friend where I enjoyed my first "cigar smoke infused" style cocktail; lunch on a private canal tour for just the two of us and the captain and his wife in Amsterdam (they docked to pick up our order from a restaurant and kept right on going); kayaking across a glacier fed lake in New Zealand, having a private dinner at an amazing tiny restaurant on the far shore, and kayaking back during sunset; hoarding a silly amount of food at a grocer in Napa while reasonably buzzed to have a picnic at our next stop-the 3rd generation wine maker ended up staying and sharing with us, and opened I can't even remember how many bottles of amazing wine; my friend and I hungover and still looking for mischief-getting invited into a closed restaurant in NOLA by the chef/owner on the high holy day of Fat Tuesday and sharing the better part of the afternoon with wine, meal, and a conversation including some of the most amazing perspectives on NOLA from a native that I've ever been enlightened with....goodness, there's more, but I think that's enough for now! Anyway, the takeaway message here is-get away from the norm and the "main strips." Those more unique experiences...they shine in your memory a bit more, and really make that experience you share with your lady friend very, very special.
Posted By: MasterZen
usually if I am in my own town, I'll ask what type of food she likes, pick the restaurant and make the reservations. If in her town, I'll ask her for a few recommendations and pick one she prefers. Always a good way to find new and great eateries, and ensure we both have a meal we enjoy.
Plan dinner together is my suggestion... but always make the reservations yourself; just seems like the courteous and manly thing to do, IMO.
As fr restaurant location... yes, I try to keep the restaurant location within a walk or short cab ride of the hotel. Who wants to burn date time on a long trip for food?
I'm sure others have many different ways of doing this.