Caving in: DiSotto Enoteca, located beneath Francesca’s on Chestnut

Too much room in a desirable neighborhood is a good thing, right? Two local restaurateurs who found themselves with extra square footage sure think so; both seized the opportunity to create not just holding tanks for waiting diners but standalone bars worthy of destination status. Or at least that was their goal. My friend Robert and I set out on a recent weeknight to take stock of the spinoffs ourselves.

The best seat in the house at River North’s Bridge Bar—an epicurean-leaning lounge created out of the space above Fulton’s on the River—is at the white marble counter directly inside the front door, otherwise known as an “activation station.” Robert and I perched and watched as a so-called bar chef in crisp whites whipped up small plates (aromatic seared scallops, raw oysters on ice; $8–$14). I had hoped we would be able to see our drinks being made, too, but that, we learned, is a different kind of activation requiring a different kind of station. No matter. The Bullshot (jerky-infused vodka, beef bouillon, lemon juice, Tabasco, and Worcestershire; $10) packs plenty of drama.

Bridge Bar is big—3,500 square feet, with a central bar that looks to be about an acre wide—so things felt rather cavernous until a group of Loop businessmen began to gather on the cushy couches. As I glanced toward the bank of windows framing Wacker Drive, a flutter of movement below caught my eye. It was the river, hurrying past, in the same green as Bridge Bar’s recently painted walls.

Robert followed my gaze. “Downstairs?” he asked, and off we headed to destination number 2: DiSotto Enoteca, located beneath Francesca’s on Chestnut in Streeterville, where Scott Harris (The Purple Pig, Davanti Enoteca, the Francesca’s empire) has built a stone-lined wine cave with a brick-barrel ceiling oozing mortar. A glass storage case houses more than $5,000 of cured meats and cheeses—a fun fact supplied by our server, Amy.

“This is cute,” I said, breaking out that cringe-inducing but apt adjective after descending a floral-carpeted staircase and claiming a seat with a prime view of the meat. It was 7:45 on a Tuesday evening, and if we hadn’t snagged our table when we did, we would have been out of luck. The crowd was a mix of neighborhood dwellers, colleagues going one bottle of wine further than they probably intended, and a few tourists. (On a subsequent Saturday around midnight, I spotted the notable nontourist and Spiaggia chef Tony Mantuano. A James Beard Award winner on-site? Always a good sign.) Robert, who lives nearby, told me DiSotto has been packed no matter what time he shows up—even when Francesca’s is closed for the night. That might have to do with the service: Amy’s guidance through the wine list was friendly and low-key. We ended up with her “go-to red,” a cabernet sauvignon from Seventy Five Wine Company in Napa Valley ($14 a glass).

I later asked Harris which idea came first, upstairs or down. “When I was shopping for space for the restaurant, the basement was optional,” he said. “I took it, knowing the room could be transformed into something unique to the neighborhood.” The wine bar—launched in January, ten months after the street-level Francesca’s—is one of the few spots east of Michigan Avenue open until 3 a.m. on Saturdays.

One night, two bars: Which came out on top? Elevation-wise, Bridge Bar wins. Chef interaction paired with a never-ho-hum cocktail list makes the place a good alternative to River North’s packed scene. But DiSotto is the real charmer. Even if, like me, you usually prefer views to vaults, DiSotto is worth the descent into Streeterville’s newly chic underworld.

Bridge Bar
315 N. LaSalle St.; bridgebarchicago.com

DiSotto Enoteca
200 E. Chestnut St.

Photograph: Chris Guillen