Hi, I've taken my kids downtown for many years. So I have some ideas. Since you have time to plan ahead, think about joining the Shedd Aquarium before you arrive. If you buy the full ticket to the aquarium, it costs $34 right now. If you get an individual membership you can take in an adult and a child. In August, the line to buy tickets is VERY VERY long. t can take an hour or more. If you have a membership, you walk right past that long line and go into the aquarium. That said, the aquarium is HUGE. But it has a lot of ambient noise and movement, which is tiring to kids. My kids generally wanted to stay about 1.5 hours. Since I live in the 'burbs, we went several times a year...for 1.5 hours each time. You might want to bypass all the hype they have about the many exhibits and buy the $8 admission to the main part of the aquarium. Your kids will remember the aquarium, and you'll not have spent a lot of cash on an expensive admission. In addition, the Field Museum is a 3 minute walk from the Aquarium, right there on the Mall. My kids always asked to walk over there and see what's up. They have a large selection of stuffed animals, insects, and other things that boys find fascinating. It doesn't have a line to get in, and it's great for another couple of hours. Another BIG cost savings...buy a family membership to the the museum in your town. That membership will get you into ALL the Chicago museums for FREE!!! That's a big deal. Most of the large museums have reciprocal memberships, allowing you to get into other museums free. But the local museums don't want to lose income. So if you buy a membership to one Chicago museum, you still have to pay to get in the others. But if you buy a membership from a museum that is not in Illinois, you get in free to all the Chicago museums. (You can ask more if I haven't explained that clearly) So...now you have gone to the Aquarium and the Field Museum. Another GREAT museum in Chicago is the Children's Museum. Your kids are the perfect ages for the Children's Museum (Free admission if you have a membership to an out of town museum) The Children's museum is at Navy Pier. My kids don't find Navy Pier all that interesting. There are restaurants, shops, and a few outdoor shows. My kids did not find those things very interesting. But they have spent HOURS at this museum. I always had to DRAG them out. You can take a boat ride from Navy Pier to the Aquarium (or visa versa) for about $8. It's a very nice ride, you get to see Chicago from the water, and it goes frequently. You looked at the Museum of Science and Industry....another great museum for kids. (I hate to repeat myself, buuutt....once again...free if you bring your out of town museum membership card) It is on the south side, a bit of a drive away from downtown. But the kids do love it. Lots of things to see and do, buttons to push. If I was time limited, I'd do the Chidren's Museum first. Lincoln Park Zoo is also free, and good. They have the largest monkey/chimp exhibit. It is on the lakefront. It is in a very fun section of town. You can also go to the Notebert Nature Museum, right next door. (It's mildly interesting..worth about 45 minutes, but it's right there) Be sure to walk through Millennium Park sometime, esp the Bean. Kids love to see the Fountain/Water area, as well as the Bean. It is good outdoor fun. Try to get a schedule of the activities going on in Milliennium Park. They have lots of free family stuff that is unique. They have families from all over the world coe and put on free street shows that you can happen into. They have free concerts almost every night. Once I was there and they had a puppet show with puppets that were 10 to 12 feet tall. These puppets had been brought in from Germany. Just wandering through Millennium Park (MP) often yields serendipitous events. Keep your eyes peeled when you arrive. There are always coupons for the top of the Hancock, as well as the Sears Tower. Ask your concierge. Regarding hotels, you will pay more to stay downtown. But I think it's really worth it to stay in the area that stretches from the Loop (Palmer House, maybe Hilton Towers)Up through Streeterville. If you stay in that general area, it will be easy for you to get around, and you will see a lot more. (I just remembered that Buckingham Fountain, in Grant Park is a fun sight in the summer. They choreograph the fountain to music, with lots of colors, after dark. If you stay in the heart of the city, you will happen upon all kinds of interesting sights. Chicago is at it's best in the summer. You can look for something on Hotwire, try to get a deal on Priceline. Lollapalooza will make the first night expensive. There are a bunch of strategies to get the cost down. I don't know that you'll get anything for $100 per night, but if you go up to $130ish and keep tring, you have enough time to make something happen. I would also check Travelzoo.com every week or so. Look under Chicago and Midwest Hotels. Often something pops up there for about $110/$120 per night. Especially when you include the baseball games you are attending, this is way more than yo can fit into the days you have. But I don't think you will go wrong with a trip to Chicago with kids. You got me going down memory lane. Sorry for the long post. Good luck, and I hope you have great memories of your time in Chicago. P.S. Don't forget the fireworks every Wed and Sat night near the Swisshotel.