Go here for everything to do in Chicago and more: http://www.explorechicago.org/city/en/things_see_do/attractions.html
Chicago is about 45 minutes from Naperville
Discover a state-of-the-art collection of architecture, landscape design and art that provide the backdrop for hundreds of free cultural programs including concerts, exhibitions, tours, and family activities. In Millennium Park, you’ll find a new kind of town square – a lively, spectacular gathering spot located in the heart of the city and a destination for Chicagoans and visitors alike.
Navy Pier is one of Chicago's most popular attractions and features more than 50 acres of parks, promenades and attractions for visitors and residents to enjoy. A 150-foot ferris wheel offers unparalleled views of Chicago's breathtaking skyline and stunning cityscape. Entertainment options abound, from the Navy Pier IMAX Theater to the Chicago Children's Museum and live entertainment year-round.
Skydeck Chicago's The Ledge
Step out for a breathtaking view with SkyDeck Chicago’s The Ledge, from 1,350 feet above the ground! The Ledge offers a unique vantage point of the surrounding cityscape in glass boxes protruding from the 103rd-floor Skydeck Chicago, formerly the Sears Tower Skydeck.