For first-time visitors to the city, there is no better introduction to the marvels of Chicago’s world-famous skyline than the ninety-minute boat tour given by the Chicago Architecture Foundation. While you cruise the Chicago River in an open-topped boat, a docent fills your head with a wealth of information about dozens of the city’s greatest hits, including the Sears Tower, the “corn cobs” (Marina City), the Wrigley and Tribune buildings and the influential skyscrapers that line Wacker Drive. Not only are the buildings easy to see and admire from this vantage point, but you’ll learn interesting tidbits about superstars (Mies van der Rohe; Skidmore, Owings & Merrill) and styles such as Art Deco and postmodernism (the latter “more a state of mind than a style of architecture,” our docent said). The Architecture Foundation also offers more than 85 tours, including bus and walking tours. The boat tours are popular, so it’s best to buy tickets online a few weeks in advance.

The Art Institute is full of treasures (including Grant Wood’s American Gothic and Edward Hopper’s Nighthawks) but small enough to manage in an afternoon. Particularly impressive is its collection of more than 2,000 European paintings and sculptures, among them Impressionist and Postimpressionist works by such artists as Monet, Degas, van Gogh and Seurat. There are also American and European decorative arts spanning several centuries, ancient Egyptian, Greek, Roman and Etruscan works and, appropriately, a smattering of interesting 19th- and 20th-century architectural details, such as ironwork fragments and stained-glass windows. The 264,000-square-foot glass, steel and limestone Modern Wing was designed by Renzo Piano and opened in 2009.

Short on time? Here are art historian Rolf Achilles’s picks for the must-sees. Start on the second floor, to the right of the Grand Staircase:

• Gallery 205: “Helen and Frederic Bartlett’s collection—basically their living room—is a lesson in how to collect: get edgy stuff. There’s Georges Seurat’s A Sunday on La Grande Jatte, from 1884, and a couple of killer Toulouse-Lautrecs, including At the Moulin Rouge. It’s amazing to think these were all in their house in Hyde Park.”
• Gallery 206: “In what other city can you see five Monet haystack paintings in a row?”
• Gallery 234A: “I adore Picasso’s The Old Guitarist, from his ‘blue period.’”
• Gallery 240: “You can also see the first two Kandinskys in the United States: Improvisation No. 30 and Painting with Troika.”
• Gallery 244: “The museum has one of the finest collections of surrealist art in the world, including Magritte’s Time Transfixed, from 1938.”
• Allerton Touch Gallery (basement): “The Joseph Cornell boxes are simply fascinating.”
• Asian Ceramics: “This 1990s installation of Japanese screens is Pritzker prize–winner Tadao Ando’s first architectural project outside Japan.”

Fans of the great architect may feel the need to make a pilgrimage to Wright’s home and studio, where he lived and worked from 1889 to 1909. You can take a guided tour of the buildings, which were renovated by the Frank Lloyd Wright Preservation Trust. Know, however, that some connoisseurs think they’re overrated, with too many reproductions and not enough original pieces. A better bet: Robie House, an uncontested masterpiece.

One of the most appealing attributes of the Lincoln Park Zoo is that it’s free, so you don’t have to deal with tickets or lines but can simply stroll in and out at any of several entrances at your leisure. The Regenstein African Journey, at the north end, is the most exotic section with pygmy hippos, warthogs and rhinos. It’s delightful to see a giraffe placidly munching tufts of greenery against a backdrop of the Chicago skyline. Children may be most captivated by the petting zoo for farm animals, on the south end.

Originally intended to coincide with the millennium, the much-anticipated park’s opening date kept being pushed further and further back as the plans became more complex and additional funds had to be raised. The result, unveiled in 2004, is magnificent—compact, so you don’t need a lot of time, but a real wow. Frank Gehry’s Pritzker Music Pavilion, an outdoor venue for free summer concerts, forms the centerpiece. It’s not just the sinuous silver petals, glinting in the sunlight, that dazzle (literally and figuratively) from all angles, but also the sound system’s trellis of steel arcs, interlacing gracefully overhead, framing skyscrapers and lush green lawn.

British artist Anish Kapoor’s beloved Cloud Gate sculpture, known to all as the Bean, nearby, is tall enough that you can walk underneath it and watch reflections in its mercury-like surface swirl into nautilus shapes. There’s also a sculpture by Henry Moore and an Isamu Noguchi fountain. Though a pleasure in all seasons, the place really comes alive in summer, when children love to splash in the Crown Fountain. At the south end of the park is the Lurie Garden, enclosed on two sides by walls of evergreens that are intended to form a sound barrier. Inside, the waving grasses create the feeling of a prairie, their soft silhouettes and soothing rustle a lovely contrast with the skyscrapers and city sounds all around.

Designed in 1908 by Frank Lloyd Wright, Robie House is a—if not the—quintessential example of Prairie-style architecture. Its sweeping horizontal structure, open layout and cantilevered roof influenced generations of designers.

Opened in 1930 by the president of Marshall Field and housed in a gorgeous Beaux Arts building on Lake Michigan, the Shedd is one of the largest indoor aquariums in the world, with 32,000 aquatic animals. In addition to piranhas, penguins, caimans, otters and jellyfish, there are amazing underground tanks where you can watch (and listen to) a beluga whale frolic with her calf. In the $45 million Wild Reef section, an underground tank with two dozens sharks inside curves over your head; you can look up and see black-tip reef sharks swimming above you (quite chilling).

The most dazzling exhibits are the extensive live coral reefs, so diverse, delicate and colorful—neon orange, bright gold, hot pink, lime green—that adults will be as mesmerized as children. Tiny electric-blue fish dart back and forth like glittering shards of glass; orange-and-white clown fish nuzzle in the waving iridescent tentacles of sea anemones; stingrays, looking like giant buckwheat pancakes, ripple past. Allow at least two hours for a visit; afterward, stroll through the surrounding park, which has paths along the water and very pretty views of the marina. Indagare Tip: Be sure to buy your ticket online before going, as the lines can be extremely long.

One of Chicago’s most beloved assets is its phenomenal public art, of which there’s a surprising amount. In the course of a twenty-minute stroll through the Loop, you can ogle more than a dozen enormous outdoor sculptures by the likes of Pablo Picasso, Marc Chagall, Alexander Calder, Claes Oldenburg, Jean Dubuffet and Joan Miró. Most are concentrated between West Randolph Street, South Wacker Drive, West Congress Parkway and Dearborn Street. Written guides are available through the Chicago Cultural Center.

The famous improvisational show that trained comedy luminaries John Belushi, Bill Murray, Gilda Radner, John Candy, Mike Myers and Eugene Levy still garners praise. And with tickets rarely costing more than $29 a show, it’s a steal. Buy tickets online before you go.