Chicago Landmarks: Book Tickets Now

Two towers, two very different takes on the same idea. Skydeck Chicago sits on the 103rd floor of Willis Tower, the taller of the two, with glass-floored ledges called The Ledge that put you directly above the city with nothing beneath your feet but air. 360 CHICAGO is on the 94th floor of the John Hancock Center on the Magnificent Mile, 1,000 feet above Michigan Avenue, and offers the TILT experience, where a glass platform tilts you out over the street at an angle.

Both give you views across four states on a clear day. They're worth comparing rather than treating as interchangeable.

Navy Pier stretches 3,300 feet into Lake Michigan from the Streeterville neighborhood and has been a fixture of the city since 1916. The Centennial Wheel, which replaced the original Ferris wheel in 2016, rises 200 feet above the pier in 42 enclosed, climate-controlled gondolas. Each ride takes around 15 minutes and covers three full rotations, enough time to take in the full spread of the lakefront and downtown skyline.

The pier itself runs year-round and has plenty going on beyond the wheel, including an IMAX theatre, a children's museum and regular summer fireworks on Wednesday and Saturday evenings.

The Chicago Theatre on State Street has been here since 1921 and is one of the oldest surviving movie palaces in the United States. Its six-story vertical sign is one of the most photographed things in the city, and the interior, with its ornate lobby, grand staircase and restored ceiling, is just as striking once you're inside. It's still a working venue today, hosting concerts and live events throughout the year.

Behind-the-scenes tours are available and take you through parts of the building the audience rarely sees.

Some of Chicago's most significant landmarks are best understood at street level. The Wrigley Building and the Tribune Tower face each other across the Chicago River at Michigan Avenue, and both reward a close look. Farther south along Michigan, the Art Institute's bronze lion statues have flanked the entrance since 1894.

The Loop itself, with its elevated train structure and mix of 19th and 20th century buildings, is a landmark district in its own right and one that most people walk through without fully registering how much is there.