How Lakeview became one of Chicago's hippest neighbourhoods

Underneath the rickety slats of the L-train tracks, the sunlight pours onto the gravel. In the distance, a train gathers speed, the elevated platform vibrating as the train passes over my head, shadows flickering on the ground as it zooms by.

The underbelly of most of these Chicago platforms is usually fairly barren, bar the odd bit of graffiti. But the space where I stand is adorned with brightly coloured pieces of art. This is the Lakeview Low-Line, a project not unlike New York’s High Line.

Spaces under the train tracks are being converted into a half-mile art walk, with the aim of connecting neighbourhoods with pop-up spaces and gardens. It’s not quite finished but this spot on Southport Avenue is the shining example of how the Low-Line will look when it’s complete.

It’s cool, artsy and enticing — just like Lakeview itself. This stretch is full of alluring joints, from the little stores selling apothecary candles to the bright-pink empanada eatery, Café Tola.

It’s a tight squeeze in the narrow café, where illustrated skateboards line the walls and a pink neon sign screams #BEST EMPANADAS. It’s not wrong, either. The ropa vieja I opt for is stuffed to the gills with Cuban braised beef, drippingly tender and laced with just enough spice to give it a bit of a kick. The crisp, bubbly little pocket makes for the perfect morning bite, but the lavender lemonade I grab alongside it is the real winner.

It’s a great snack for ambling, too. A stroll past the wooden houses on wide side-streets takes me to the shores of Lake Michigan, where yachts bob along the water and impossibly fit youths jog alongside glossy labradoodles. The impossibly unfit follow my lead and head to Stan’s Donuts for an iced coffee and an original glazed.

This is all still under the Lakeview umbrella — the neighbourhood spans the area from the lakeshore right back to Ravenswood Ave, and includes in its borders one of the city’s biggest hitters, Wrigley Field. Right over the street from the Chicago Cubs baseballpark is the brand new Hotel Zachary, a sleek, boutiquey get-up with killer views over the stadium. But look in the opposite direction and you’ll get the other Lakeview perspective: the low rooftops of wood houses give way to the glittering city skyline in the background.

A short walk away, the tiny Mercury Theater is possibly the smallest home to big Broadway shows — when I visit, Avenue Q has extended its run on the main stage, and the newly opened Venus Cabaret Theater is currently hosting a revival of Pippin.

Another Southport staple is Corridor Brewery & Provisions, a utilitarian-chic restaurant with bikes on the wall and a craft brewery in the back. The beer makes its way onto the menu, as you might expect — the white-bean hummus is whipped up with the Wizard Fight IPA and a smack of rosemary, and the beer cheese is a gooey, melty ode to everything sinful.

But the real neighbourhood showstopper is the Music Box Theatre, a shining tribute to old-school American movie houses. Open nearly 90 years, the cinema is stuffed with vintage features, from the faux-marble arches to the soaring drapes of red velvet in front of the screen. Hell, it’s even got its own friendly ghost, Whitey, who managed the theatre from the day it opened in 1929, until the day he died in 1977 (on a couch in the lobby, natch). He now roams the aisles, keeping watch on the door where troublesome kids used to sneak in, and dropping the curtain on organists who aren’t to his liking.

The deep-blue ceiling in the main screen is speckled with stars, and the ancient lighting means even when the lights are up, the space is dark.

So dark, in fact, that when I sneak into a Looney Tunes marathon on a Saturday afternoon, I ease myself precariously into a seat not knowing until the last second if I’ll find myself in someone’s lap. It’s pure luck that I don’t (though it would make for quite the meet-cute).

And there are enough of those happening as it is. After a peek at the food truck surrounded by couples on the back patio, I sit for a while in the lounge, plonking myself on a battered leather chesterfield surrounded by old TV sets, stacks of board games and, brilliantly, a framed picture of actor Nick Offerman (he performed here in 2016).

I grab a tattered hardback about old Hollywood musicals, mostly so I can inconspicuously eavesdrop on the pair sitting on the adjacent couch. They’re navigating the conversation minefield that comes with a first date, before the chat shifts to favourite movies and starlets. Soon they’re onto the second round of Manhattans and planning which Robin Williams movies they’ll see in the upcoming retrospective.

I grab a negroni for myself and think about how easily I too could live here — spending my days watching old movies, strolling the Low-Line, and eating way, way too many empanadas.

Details

British Airways (ba.com) flies to Chicago from £263 return. Rates at Hotel Zachary (marriott.com) start at £161, room only. See choosechicago.com and lakeviewchamber.com.