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There's no need to hire a babysitter on this trip -- Chicago offers plenty of diversion for youngsters, so be sure to plan ahead and involve your kids as you outline your trip. Museums have special rates for children, and Navy Pier -- with its games, IMAX movies, and Ferris wheel -- is like an amusement park in the middle of the city. Many restaurants provide children's menus. When packing, include items that will keep your children busy en route. On sightseeing days try to schedule activities of special interest to your children. When you arrive, pick up a copy of Chicago Parent, a monthly publication with event and resource listings, available free at locations throughout the city.
If you're up for a bit of exploration on a road less-traveled in the Windy City, pick up the "Small Snack" map series from artist Ryan Maconochie. The maps were created to send adventurers on a more eclectic path around the city, encouraging visits to Wicker Park, Bucktown, Ukrainian Village, and the East Village. The map includes the best things "to eat, drink, and do" for those who are up for changing their routines.
The ideal time to visit is summer or fall. Summer offers a nonstop selection of special events and outdoor activities, but you'll also be dealing with the biggest crowds and periods of hot, muggy weather. Autumn days are generally sunny, and the crowds at major tourist attractions grow thinner -- you don't have to worry about snow until late November at the earliest. Spring is extremely unpredictable, with dramatic fluctuations of cold and warm weather, and usually lots of rain. If your top priority is indoor cultural sights, winter's not such a bad time to visit: no lines at museums, the cheapest rates at hotels, and the pride that comes with slogging through the slush with the natives.