Start your day by looking beyond Chicago’s urban jungle of skyscrapers. The city has plenty of vibrant green spaces to be seen by bike or Segway tour. Millennium Park, within the larger Grant Park, has become one of the city’s most popular attractions since it opened in 2004. Stretching across 25 acres (10 hectares), the park’s highlights range from the verdant Lurie Garden to the playful Crown Fountain and Anish Kapoor’s reflective Cloud Gate sculpture, commonly known as “The Bean.”

From the soaring spires of the Willis Tower and the John Hancock Center to the famous Marina City buildings and the landmarks along Magnificent Mile, Chicago is an architecture lover’s city. One of the best ways to take in the sights is on a cruise along the Chicago River. Find a seat on the deck, and crane your neck upward as your tour guide shares stories about how the city’s skyline came to be. Alternatively, a walking tour lets you get intimate with the landmarks, head into building lobbies to admire interior architecture, and delve into their history.

Chicago is a skyscraper city—until One World Trade Center debuted in New York City in 2013, the Willis Tower (formerly known as Sears Tower) was the tallest building in the Western Hemisphere. In addition to being a Chicago landmark, the building offers some of the best views of the cityscape and Lake Michigan beyond. Book Skydeck admission tickets to take an elevator 100 floors above the city and admire a panoramic perspective of Chicago after dark. If that isn’t sufficiently lofty, evening helicopter tours also provide an excellent aerial vantage point for night sightseeing.