You cannot visit a big city without checking out the architecture. The mix of old and new in Chicago is entertaining. Remember that Chicago does not have many very old buildings. The great Chicago fire burnt down much of the city. There are many from the early to mid 1900’s when the city was rebuilt and expanded further. We did not seek out the Sears Tower on this trip because we have been there many times.
Learning on the go tip: If you are visiting Chicago (especially with children that are 8 or older) read about the Chicago Fire before you go. You can check a book out of your local library or read about it online. By connecting history with the personal experience of visiting the city you and your children will have a deeper understanding.