Feel the Breeze
You might hear Lake Shore Drive in Chicago, bordered by Lake Michigan to the east and parkland on the west, described as the prettiest urban stretch in America. Rightly so.
The Lakefront trail can get a bit congested so why not get some perspective on the skyline (and some fresh air) and take an Architecture River Cruise. Back on land, the Art Institute offers one of the best art collections in the world, without the massive crowds you find in Paris or New York.
Embrace the tourist cliché (it got popular for a reason), walk through Millennium Park and take a photo at Anish Kapoor’s Cloud Gate (which you might to just call “the bean”). On a summer night, you might catch music or a movie at the Pritzer Pavillion.
Further north, in Lincoln Park, you’ll find beaches, the zoo, soccer fields, bird sanctuaries, and North Pond, one of the city’s most-celebrated Michelin-starred restaurants. But you might want to save that for another day.