Located along the shores of Lake Michigan, Chicago—the largest city in Illinois and the third largest in the United States—offers a wealth of art, music, historical, and architectural experiences. Culture lovers can stroll through Millennium Park and the Loop to view outdoor art (including the iconic “Bean”), tour world-class museums such as the Art Institute of Chicago, or cruise the Chicago River to see modern landmark gems. To meet the locals, buy a ticket for a ball game; catch some live blues or jazz (both of which have deep roots in Chicago) at a club; or laugh at the comedy acts at Second City, where many top comedians launched their careers.
Top attractions in Chicago
1. Skydeck Chicago at Willis Tower (Sears Tower)
Willis Tower can be seen from across Chicago and is a highlight on most sightseeing tours and Chicago River cruises. To head to the top, book admission tickets in advance to skip the long lines—the 70-second elevator journey to Skydeck Chicago includes a film which covers the tower’s history. Then, admire the city from above and take a turn on the glass-bottomed Ledge; alternatively, book an early-access breakfast, lunch, or dinner at the 99th floor or Skydeck.
2. The Magnificent Mile
The Magnificent Mile is one of the most prestigious sections of pavement in the country—a Chicago must-do, even if you’re only window-shopping. Its central location and prominent place in the city’s cultural landscape mean it’s featured on just about every sightseeing tour, whether on foot, bus, bicycle, trolley, or Segway. To get a sweeping view of the Magnificent Mile, head up to 360 Chicago, an observation deck inside the John Hancock building.
3. Navy Pier
Most Chicago sightseeing tours (by foot, bike, bus, or Segway) include a stop at Navy Pier, which buts right up against the Streeterville neighborhood and the distinctive Chicago skyline—and is one of the largest entertainment complexes in the United States. The pier is also a departure point for the must-do Chicago architecture river cruises and classic lake tours. For kids, Navy Pier features the Chicago Children’s Museum, plus a collection of high-tech rides, hands-on fountains, kid-focused educational exhibits, restaurants, and trinket vendors that will transport your child into the realm of overstimulated joy. Adults will appreciate the lakefront views, cool breezes, and a ride on the gigantic Ferris wheel or classic carousel. Skyline Stage, a 1,500-seat rooftop venue under a canopy, plays host to a variety of shows throughout the summer; and on Wednesdays and Saturdays, the pier puts on a whopping fireworks show.
4. Chicago River
The most popular way to explore the Chicago River is on a cruise, in particular a Chicago architecture river cruise, which offers an overview of the city’s history and building architecture. You can combine your cruise with a Chicago city tour, food tour, South Side tour, speedboat ride along Lake Michigan, or access to the Willis Tower. Kayak tours are also popular, including a nighttime ghosts and gangsters tour.