Chicago is clean, friendly, and easier to get around than most people expect, and the food alone is worth the trip for a family.
Start with deep dish pizza, the Chicago institution, a pie so thick it is more casserole than pizza, and kids are wide eyed at the first slice. Order one early, it takes a while to bake. The Chicago hot dog, loaded with toppings and famously never ketchup, is a fun cheap lunch, and Italian beef sandwiches are the other local specialty. No one goes hungry here.
The single best overview of the city is the architecture boat tour on the river. A guide points out the famous buildings as you float between the skyscrapers, and even kids find it interesting for the hour it runs, especially from the open top deck. It is the thing I recommend most to first timers.
Getting around, the L, the elevated train, is cheap, easy, and a fun ride for kids as it rattles above and below the streets. You do not need a car downtown.
Come late spring through early fall. Chicago winters are bitterly cold and windy, though the holiday season has its own charm if you bundle up.
The full Chicago with kids guide is here: Chicago With Kids. Want it built around your family? Work with me.
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