Only 30 miles west of Chicago and easily reached by Metra's BNSF line, Naperville has built one of the most livable downtowns in the Chicago suburbs. The Riverwalk runs 1.75 miles along the DuPage River, lined with foot bridges, fountains, and outdoor seating — a genuinely pleasant place to spend an hour or two, especially in warm weather. The downtown blocks radiating off it have enough independent restaurants and shops to fill an afternoon without feeling like a mall.
The 13-acre Naper Settlement is the main cultural draw — an outdoor living history museum that reconstructs mid-19th-century Illinois with costumed interpreters, a fort, a one-room schoolhouse, and regular seasonal events. It takes two or three hours to do properly and works well with children. In summer, Centennial Beach — a former quarry converted into a public swimming facility — draws locals who have figured out that it is far better than it sounds.
With a population of around 150,000, Naperville is a real city rather than a bedroom suburb, and the food scene reflects it. You can eat well here. Take the Metra from Chicago Union Station or Ogilvie Transportation Center and you arrive right in the heart of town, making this one of the easiest Chicago day trips to pull off without a car.