Chicago
Chicago, the “Windy City,” is also called the “Wild Onion” (the name Chicago comes from the Native American word shikaakwa), or “Second City,” the city rebuilt after the Great Fire of 1871. In Chicago, kids can go up Willis (Sears) Tower, the tallest skyscraper in North America, check out dinosaurs and Impressionist paintings in the museums, soar on a giant ferris wheel or ride the elevated train in the Loop.
Tips for Chicago before you go and while you're there - best water play areas, museum-going, taking trains and buses, avoid long ticket lines for attractions in summer, and more.
Ride the free trolleys - Chicago has four different free trolleys, with stops at places you'll want to explore. The red, yellow and green trolleys go from the Willis Tower to the Field Museum, Water Tower and Navy Pier, daily in summer, weekends the rest of the year. The blue trolley goes in a loop from N. Michigan Ave. to Navy Pier, daily year round.
Street performers on Michigan Ave. - Just stroll up and down Michigan Ave., and there are all kinds of musicians - drummers drumming on yellow buckets, saxophone, tuba players, impromptu blues singers, and vendors making colorful balloon hats.
Go to a baseball game - Wrigley Field, an old-fashioned open air ball park, is a wonderful place to see a baseball game. Built in 1914 and the second oldest in America, the field hosts the Chicago Cubs baseball team. April through September, there are beind the scenes tours of this historic ball park.
Fun food
Chicago style hot dogs - load up your hot dogs with all the toppings, mustard, onion, relish, pickle, celery salt (ketchup is a special request). Chicago is also famous for its deep dish pizza, so sample pizza around the city. Caramel popcorn was practically invented in Chicago, kids will enjoy a bag full. For a dessert, there's Eli's cheesecake.
Marshall Field's (now Macy's) department store on State St. has long been a popular family destination for lunch (chicken pot pie and desserts) in the Walnut Room. The Tiffany ceiling, chandeliers and dark wood paneling are a glimpse into a previous century, and in December, the Christmas tree.
Here's our own Travel for Kids hand-picked list of family hotels, all styles and price ranges, convenient to fun things to do with kids in Chicago: