Chicago is an excellent stop over for anyone, especially for families. With a city of 2.7 million citizens, you can expect there to be all sorts of events that you can take in and activities you can do. So, no matter the age or what time of year you travel, there is no limit to what you can do or how much enjoyment you are going to get out of the city.
Field Museum Lake Shore
The Field Museum is an excellent place to take in some rather incredible sights. As soon as you walk in you are going to come face to face with "Sue", the full body T-rex skeleton. While this area is free, there are different exhibits that rotate throughout the year. From young to old, this is an excellent location that you can take in history, have fun and learn a thing or two.
Baseball Wrigleyville/South Side
Whether you are a Cubs fan or a White Sox fan, there is some excellent baseball to be had in Chicago. The two teams offer something completely different, and with one in the American League and the other in the National League, you don't have to worry about routing for a team that plays in the same division as your favorite team. Wrigleyville is where you will find the Cubs, and while this is one of America's favorite underachieving sports franchises, you are sure to have fun at the game. There historical elements of the stadium are extremely fun and don't have all the glitz and glamor you'll find in other locations. On the other end, The White Sox on the south side won a World Series in 2005 and also offers a fun side to a baseball game. Plus, if you are up for a drive, the Milwaukee Brewers play just an hour north of Chicago, so you can actually see three different games over the course of some weekends.
American Girl Michigan Avenue
While this probably isn't for some, American Girl Dolls are staples for many individuals and is a must for any lover of the dolls. While these dolls are not cheap, there is something about entering the building that many mothers and daughters share with one another forever. Just make sure to bring your pocketbook, because most dolls and accessories are going to cost you well over $100.
Navy Pier
The Navy Pier is an excellent hot spot for anyone visiting the city. There are all sorts of activities that you can take in for free, plus an excellent ferris wheel ride that you can give you views of the entire city. From restaurants to amusement park rides, this is a really great spot for anyone coming to the city, regardless of how many times you have been to the city.
Chicago is an excellent location for you to bring the entire family to. No matter how many times you have been to the city or what everyone wants to do while in the city.