I'm attending a work conference in Chicago this September and am really excited because I've never been. DH is buying a ticket on my flights and tagging along for the four day trip. We'll have the first full day together (and the Cubs are home so you bet we'll be at Wrigley that day), and then the next three days, I'm basically in the conference from 7am-3pm, giving me time with DH every late afternoon and night.
The hotel/conference is right near Millennium Park and the Theater district and it looks like there are tons of cool places nearby. Looking for 1) great dinner spots or fun nighttime activities to do with DH, and 2) ideas for DH when he's by himself during the day. Without suggestions he would probably just hang in the hotel, go to the gym, watch movies, drink in the hotel lounge, so I'd love to give him some adventure guidance.