Going to spend a few days in Chicago with my ATF.  

I would check out yelp, reddit, and some other venues for that type of info.  best of luck.

Stay downtown. If you're looking to have fun, you can't go wrong. Parking is expensive, but well worth it if you can get in and out parking at the hotel.
Sight seeing. Gold Coast beach is very beautiful, and everyone there is ripped and hot. She can put on her bikini and splash away... or play volleyball.
Divvy biking - for a little fun, if she's active or feels comfortable.
There are a ton of rooftop bars. The Wit has a superb one, as well as Epic bar. Amazing view at Epic, and people in their 30's and up hang there. Wit has models as servers, and is very classy and dress up. Have to reserve a seat.
Dinner - Oh my, way too many places to tell. It depends if you're staying in the Loop or River North. If you want super upscale, romantic, dainty and quaint, or a steak house. Also budget plays a big role.
Downtown there is a great blues bar called Legends. They have great acts that come in.  
Comedy clubs are fun, but check to see if the comedians will make her (and you) laugh. The last thing you need is a bad comic lol. The best way to check on that is to pull them up on YouTube after you've seen who is going to be highlighted that night. There are plenty of places downtown and around.
Piano bars are super sweet.
Or, y'all can go to some good ole' karaoke and sing some Sonny and Cher!

No response because they are probably PMing which is probably preferred.  

I don't know if you guys are into these sorts of things but did you know that Chicago is ranked the number two city in the world for Art?  The Art Institute and MOCA are awesome experiences.  Also, the museums, I believe, offer a day pass that gets you into most, if not all of them.  The Aquarium is a lot of fun as well.  Maybe one day I could convince one of the providers to mate with me while we watch the dolphins, though I'm quite sure there will be an up-charge.  LMAO.

What can a goose do, that a duck can’t, that a lawyer should?
Stick their bill up their ass.