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Who’s watching who at this beloved city zoo, which attracts more than three million visitors annually.

Built in 1914, this is the USA’s oldest National League baseball park. Home team, the Chicago Cubs, haven’t won a World Series championship since 1908 (before the field even existed), but that doesn’t stop Northsiders from being behind them every step of the way. In season (March– September), spending an afternoon cheering on the “Cubbies” in this marvelous stadium, with its ivy-clad walls, is a quintessential Chicago experience.

This museum’s sloping, beige exterior was inspired by the sand dunes that once occupied its site. Inside are a whole host of engrossing interactive exhibits, the highlight being the walk-through Butterfly Haven, a light-filled space, constantly aflutter. The outdoor grounds, with their native wildflowers and prairie grasses, are perfect for a peaceful walk or rest.

Strolling down North Halsted Street, it’s fairly evident you’re in Chicago’s gay neighborhood when you hit shops called Gay Mart, Cupid’s Treasures, and a club named Manhole. Just 30 years ago, this area – officially East Lakeview – was pretty shabby, the bars were without signs, and parking was a cinch. But now buzzing Boys Town is gay central – by day and by night.

This area of unique boutiques is a boon for fashionistas. Dozens of shops here sell everything from sophisticated evening wear to high-end accessories: many of the stores occupy renovated Victorian town homes, set along pretty tree-lined streets.

Focusing on Illinois and Chicago history since settler days, this museum was established in 1856 and is the city’s oldest cultural institution. One of the society’s first donors bequeathed his collection of Lincoln memorabilia: the ex-president’s deathbed is one of the items displayed. Visitors can also climb aboard the Pioneer locomotive, while events such as the World’s Columbian Exposition and the Great Chicago Fire (see 1871: Great Chicago Fire), are brought to life by photographs, decorative arts, and other exhibits. There are also costumes belonging to famous local figures including sportsman Michael Jordan.

Take a free trip to the tropics at this spacious conservatory, just next to Lincoln Park Zoo. Opened in 1893, the glass structure is a year-round, 80° F (40° C) sanctuary from the Chicago’s bustle, and offers a welcome respite from the city’s long winters. Paths meander past lush palms, flourishing ferns, and exquisite 100-year-old orchids. Avoid the crowds by coming on a weekday when, unless a seasonal show is taking place, it’s a quiet space, with the sound of trickling water as background music.

When summer finally graces Chicago with its presence, locals of all ages and nationalities converge on this short, but inviting stretch of beach. Running along its edge is the lakefront path, where cyclists, in-line skaters, runners, and walkers stream by. An outdoor gym gives confident folks a place to strut their stuff, sand volleyball courts allow the energetic to let off steam, and the rooftop bar of the steamship-shaped beach house is perfect for downing a cool drink while lazily watching the activity below.

The Benevolent and Protective Order of Elks, an American fraternity (founded in 1868 and still going strong), built this magnificent structure in 1926 to honor its World War I veterans. It’s since been re-dedicated to pay homage to World War II, Korean and Vietnam war veterans. Two larger-than-life elk statues flank the wide entrance steps, while inside, every inch is richly decorated. The 100-ft (30-m) marble rotunda, murals depicting the Sermon on the Mount, intricate windows, and allegorical bronze sculptures are awe-inspiring.

Nostalgic German immigrant Francis Dewes, a self-made millionaire, commissioned this elaborate home in 1896. Built in the eclectic Gründerzeit style – a German counterpart to Beaux Arts – its entrance steps, stone statues, and ornate carved curlicues certainly stand out from the neat rows of adjacent brick apartment buildings. Interior highlights include mosaic floors, a fountain, and wrought-iron chandeliers.