48 Hours in Chicago (Kids too!)
Chicago might be the best big-city value in America for families. The lakefront is free, several world-class museums have free days for Illinois residents (and cheap days for everyone else), and the CTA beats paying $60 a night to park.
Day one: the classics, mostly free
Start at Millennium Park — The Bean, the Crown Fountain (bring a towel, the kids will get in), and Maggie Daley Park’s play garden, which would be the highlight of most cities on its own. Walk the lakefront to Navy Pier for the view, skip the rides.
Day two: museums and deep dish
Pick one museum and do it properly. With kids under 10, the Museum of Science and Industry wins. Lunch is the deep dish debate — our take: the famous places are fine, but the neighborhood spot near our hotel was better and half the wait.
The money move: stay near a CTA line, not downtown
We stayed two Blue Line stops from the Loop, paid roughly half the downtown rate, and the “L” ride was — according to the kids — a top-three attraction of the trip.