The second-largest art museum in the country, the Art Institute houses treasures from around the globe, including a fantastic selection of Impressionist and Post-Impressionist paintings. Top billing goes to Georges Seurat’s pointillist A Sunday on La Grande Jatte and Grant Wood’s American Gothic. The Modern Wing hangs Picassos and Miros on its 3rd floor.
Wherever you enter (i.e. Michigan Ave or Monroe Ave), pick up the free Visitor Guide booklet with maps and “what to see in an hour” instructions. Or take a free 60-minute Highlights Tour, led by a docent. It departs at noon or 2 pm on varying days.
Better yet, download the Art Institute’s free app – either at home or using the museum’s wi-fi. It offers several tours through the collection, covering everything from highlights to architecture to pop art.
The 3rd-floor contemporary sculpture garden is always free. It provides cool city views and connects to Millennium Park via the mod, pedestrian-only Nichols Bridgeway. The north and south gardens along Michigan Ave are also perennially free and sculpture laden.
The museum is free Thursday evenings from 5-8 pm (though this applies to Illinois residents only). There’s also a winter break for IL residents, with free admission Mon-Fri from early January through mid-February.