7 Best Sights in Lakeview, Chicago

You need not be a baseball fan to enjoy a visit to the nation's second-oldest major league ballpark—venerable, ivy-covered Wrigley Field. This hallowed stadium hosted its first major league game in 1914 and has been home to the Chicago Cubs since 1916; the Bears also played here for a half-century before decamping to Soldier Field in 1970. The original hand-operated scoreboard is still in use today, and even though updates and renovations have added plenty of digital screen space, the character that makes this place so special remains intact. If you look up along Sheffield and Waveland Avenues beyond the bleachers, you can see the rooftop patios where baseball fans pay high prices to cheer for the home team; devoted "ball hawks" sit in lawn chairs on Sheffield, waiting for foul balls and home runs to fly their way. While you're here, check out the Harry Caray statue commemorating the late Cubs announcer, or hang out after the game in Gallagher Way, the new plaza built after the team was acquired from the Tribune Company by the Ricketts family. Big-name concerts by the likes of Pearl Jam and Bruce Springsteen are also staged here when the team is out of town.

After entering at Clark Street and Irving Park Road, you'll quickly discover that this graveyard has crypts that are almost as strikingly designed as the city skyline. A number of Chicago's most prominent citizens, including city planner Daniel Burnham, railroad magnate George Pullman, and retail icon Marshall Field, are spending eternity here. Architect Louis Sullivan (also a resident) designed some of its more elaborate mausoleums. Free maps, available at the cemetery office, will help you find your way around the pastoral 119-acre property.

Southport's main claim to fame is this 1929 movie house, which shows independent and classic films on its two screens. Live organ music provides a retro preamble. Before the house lights dim, look up to admire twinkling stars and clouds on the ceiling.

Just east of Wrigleyville lies this section of Lakeview; it's been a major "gayborhood" since the 1970s, which also makes it one of the country's first. In recent years there's been an admirable push by the local queer community to go beyond the gendered moniker of "Boystown" and reflect the more inclusive LGBTQIA+ world, which is why you'll hear the area referred to as Northalsted more often these days (as most of the queer-oriented shops, bars, and restaurants are concentrated on and around North Halsted Street). In June the area becomes a sea of people, when tens of thousands attend the annual Pride Fest as it floats down the street. One of the city's largest music-focused neighborhood street fests, Northalsted Market Days, floods the area with visitors once again in August.

The Southport Corridor, as this stretch of pavement is known, is lined with independent shops and high-end boutique chains to serve the area's well-dressed urban professionals with money to burn. Those stores are peppered amongst neighborhood pizza joints and classic taverns, bookended by music venue Schubas Tavern to the south and the historic independent movie theater The Music Box at the north. 

The strip from Lake Shore Drive to Sheffield has an entirely different character than the residential streets nearby. Yes, it has Starbucks and Potbelly, but funky shops, tattoo parlors, and vintage-clothing stores add an interesting, eclectic feel. Just past the El tracks at Sheffield, you'll see the Vic Theatre. Once a luxurious vaudeville venue, it's now a popular spot for live music; on Brew & View nights, when multiple bars are open and the mood is most festive, on-stage acts are replaced by movie screenings.

Two- and three-story gray-stone houses and other residential buildings line the quiet, leafy side streets heading east and west of Boystown. Wandering along them, you might even feel transported back in time to 1920s or '30s Chicago. In 2008 a stretch of Newport Avenue between Clark and Halsted was temporarily transformed into a cobblestone thoroughfare for the John Dillinger flick Public Enemies, starring Johnny Depp.