<p>I went to Chicago in October and enjoyed ourselves very much. My first advice isn't photography related, but you'll be very, very happy you did. Get a City Pass if you plan on going to the top of the Willis Building (Sears Tower). There were lines that were at least 1.5 to 2 hours long just to get to the observation deck. With the City Pass we were on the observation deck within 25 - 30 minutes from entering the building. It was well worth the money. It was also great for the other exhibits we went to.<br /> <br /> Photography-wise, I took the D700, 28-300, 24mm f/1.4, 85mm f/1.4, 50mm f/1.4, and a 16mm f/2.8 fisheye. I also took a Canon Powershot SD950. The little camera got used a bit, but the Nikon D700 and the 28-300 got the most workout. At night, the other lenses were used. It was really, really heavy to carry the bag all over town, but that was my choice. I was happy I did most of the time. Here's some photos I ended up with: https://www.flickr.com/photos/nathantw/sets/72157636916467323/<br /> <br /> When I went to New York a couple years ago I only brought my Canon Powershot and was happy I did. I had gone there previously with all my gear and that last trip I just wanted to go without worrying about carrying a lot of equipment. There were quite a few times I wished I had my Nikon, but I got over it.<br /> <br /> So, what should the OP take? I say just use what you own. I would take the 24-120, 70-300, and the 50mm. If you're willing to carry it all, then by all means, use what you own. If you don't want to carry it all, bring one lens and be done with it. Remember, you don't need to take pictures of EVERYTHING and be a breathing movie camera. Just take pictures of what you like. In the long run the photos you will cherish, though, will be the ones of you and your family. All the others are just for fun, but the family ones are the most important, so make sure you take the photos, no matter how cheesy they are, in front of the tourist attractions. Good luck and enjoy yourself!</p>