You are from San Antonio, you can have steak anytime, anyplace. If you want a sense of Chicago, without having to travel too far off of One Mag Mile. Take the Chicago Bus, westbound, you board at the intersection of Michigan and Chicago, on the north west corner. Get off a bit west of the expressway for Green Zebra. Chicago Transit Authority, CTA is $2.50 per person per way, this assumes you do not buy a cheaper one day visitor pass at the airport at O'Hare, assuming that product is still available.
Green Zebra has a cool contemporary look and is perfect for a date night. My husband and I have done birthdays and anniversaries there. A couple of years ago we did a birthday party there with all omnivores including a local chef who just adored their meals. They have seasonal, locally/regionally sourced, small-plate offerings. It is primarily vegetarian, but generally you will find one fowl or seafood dish on the menu. Shawn McClain is one of the hottest chefs in the city. It takes a lot of talent to have a steakhouse, a seafood spot, and a zen vegetarian spot as well. He has done all of them well. I don't think he is in the kitchen, because I heard he was opening a spot in Vegas, but he is homegrown.
Not that you care, but my first visit there included a visit by Gwyneth Paltrow and her husband. About a year ago, I was eating brunch there with a friend and Chicago's own Stefanie Izzard, winner of Top Chef Chicago was also dining there with a friend. The food is good, and accessible. Luckily, when there is a celeb dining they are very low-key, so no big deal at all.
After dinner and coffee (Intelligentsia if I recall correctly, a fabulous local roaster) grab a taxi back, if you don't see the eastbound Chicago Avenue bus, by the way, if you have a smartphone you can track buses by the minute at ctabustracker.com.
Then for Jazz, you head to the legendary JazzShowcase. This place is so serious, that it has always offered an afternoon show on the weekends for families to bring the kids. I have had the honor of seeing McCoy Tyner, Ahmad Jamal, Art Blakely, and Dee Dee Bridgewater, to name a few, play in this intimate setting.
Peace,
http://www.jazzshowcase.com/http://www.greenzebrachicago.com/about.html