The Run Down

Head to Lakeview for a low-key date night. You'll start at a neighborhood cocktail bar for pre-dinner drinks, then grab dinner at a place that combines French-Canadian comfort food with fine dining sensibilities. Afterward, you'll walk a few blocks to a tavern where you'll find a live performance nearly every night of the week. Depending on the night, you might be rocking to an upcoming R&B singer on a national tour, or you may find yourself swaying to the sweet sounds of a local bluegrass folk singer.

1. Cocktails @ Love Street

2. Comfort Food @ Dear Margaret

3. Live Music @ Schubas

1. Love Street

Your first stop is a neighborhood cocktail bar called Love Street. Sitting on a quiet corner, it blends in with the massive single family homes and low-rise apartment buildings surrounding it. Close your eyes and imagine the ideal, tree-lined street in Lakeview. This is what you’d see.

The bar is long and narrow. The light is dim. The style blends old Hollywood glam with a darker touch. Think of Tom Cruise’s character in “Interview with a Vampire,” pale in a ruffled shirt, owning a bar in Chicago. This is that place.

That’s the last of the vampire fan fiction, back to this guide. If you and your date want to snuggle up, a few booths are in the back of the bar for maximum romance.  Their cocktail program deserves mention. They’re creative, and on can stand with the best in the city. Each specialty drink costs fourteen dollars. If you can’t decide, ask for the ‘dealer’s choice.’

We were dealt this mezcal cocktail with poblano chile, absinthe, pineapple, lime, agave, and cucumber.

2. Dear Margaret

After cocktails, head to dinner inside a building resembling grandma’s country farmhouse.

Dear Margaret, a French-Canadian restaurant, occupies a small storefront along Lincoln Ave. It made its mark on the Chicago food scene almost immediately after it opened. Here’s an in-depth review from Louisa Chu of the Chicago Tribune, who calls it one of the best Midwestern restaurants.

Here are a few things to remember as you plan your visit.

– Only open for dinner Wed-Sun (starting at 5 pm and last seating at 9:45 pm (8:45 pm on Sun))

– Reservations are recommended and can be booked through Tock

Let’s talk about the food. The restaurant honors Chef Ryan Brousseau’s grandmother, Margaret. As expected, a grandma-inspired menu is filled with comfort food, the French-Canadian kind.

That means things like pomme frites, fried smelt, braised rabbit, stuffed lamb, and charcuterie boards. All prepared with a fine dining touch.

3. Schubas

After a few cocktails and a full stomach, the night ends down the street at Schubas Tavern. This isn’t just any regular bar. This designated Chicago Historic Landmark has been around for over 100 years. It opened up in 1903 and was first owned by the Schlitz brewery, which at that time, had several “Schlitz” bars across Chicago. Today, Schubas is in the hands of private owners, but you can still see many of the original designs and Schlitz pieces in the bar.

Aside from its architectural significance, Schubas is probably best known as one of Chicago’s go-to small venues for live music and performances.

This is what you’ll see when you first walk into the bar. The front of the house has your normal bar set up. By the way, this is a great, low-key place to grab a drink and watch a game, even if there isn’t a performance.

Keep moving towards the back; you’ll find nooks and crannies throughout the space for more privacy. Go even further, and you’ll run into the back room with the performance space that hosts live acts nearly every night of the week. It’s mainly music performances but they’ll throw in comedy shows, storytelling events, and live podcast recordings every now and then. The performance venue probably fits around 150 people.  Many of the acts that come through are folks on the precipice of stardom. In the past, future stars like Janelle Monáe and My Morning Jacket have made their way through Schubas. Tickets to shows range between $5 and $20, which is not a bad price to watch a potential up-and-coming superstar.