The Run Down

We're headed to Lakeview for a low key date night of comfort food, libations, and live music. 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. Afterwards, you'll walk a few blocks down the street 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. Here are the details.

1. Cocktails @ Love Street

2. Comfort Food @ Dear Margaret

3. Live Music @ Schubas

1. Love Street

Our first stop is at a neighborhood cocktail bar called Love Street. It’s on a quiet corner blending in with the huge single family homes and low rise apartment buildings surrounding it. It’s probably what you’d imagine if someone asked you to close your eyes and picture the perfect tree-lined residential street in Lakeview.

The bar takes up a long and narrow space. It’s dimly lit and its design combines mid-century Hollywood glam with goth aesthetics. If Tom Cruise’s character from Interview with the Vampire opened a bar in Chicago, then this would be the spot.

I can see it now, a pale Tom Cruise is mixing cocktails behind the bar and wearing that pirate shirt with the ruffled collar. He tries to hide the fact that he is a vampire, but it’s painfully obvious to everyone, and then silly hijinks ensue.

Feel free to use this as a first date icebreaker or pitch it as show to Netflix.

That’s the last of the vampire fan fiction. Back to this guide. If you and your date want to snuggle up, there are a few booths in the back of the bar for maximum romance.  Finally, a few words need to be said about their cocktail program. They have a creative menu on par with any good craft cocktail place you’ll find in the city. Think things like this mezcal cocktail pictured below with poblano chile, absinthe, pineapple, lime, agave, and cucumber.

All their specialty cocktails are $14 and if you’re unsure what you want, you can ask for the “dealers choice” and the bartender will whip up a concoction of their own. 

2. Dear Margaret

After cocktails, we’ve got dinner in what looks like grandma’s country farmhouse, but found right in the middle of the city.

We’re at Dear Margaret, a French-Canadian restaurant that, even with the added challenge of starting  during the first pandemic winter (how dystopian does that sound?), has made it’s mark on the Chicago food scene. 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 keep in mind as you plan your visit.

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

– Reservations recommended and can be booked through Tock

Now onto the food. This restaurant was founded as an ode to Executive Chef Ryan Brousseau’s grandmother, Margaret. And as expected, a grandma-inspired restaurant means a menu full of warm and hearty comfort food — French-Canadian comfort food.

That means things like pomme frites, fried smelt, braised rabbit, stuffed lamb and charcuterie boards all with a fine dining twist. Here are pictures for your viewing pleasure.

3. Schubas

After a few cocktails and a full stomach, we’re going to end the night down the street to Schubas Tavern. This isn’t just any regular bar. This is actually a designated Chicago Historic Landmark that’s been around for over 100 years. It opened up in 1903 and was originally owned by the Schlitz brewery, which at that time, opened up a number of “Schlitz” bars across Chicago. Today, Schubas is in the hand 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 for being 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. This is the front of the house with 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 going on.

Keep on going back and you’ll find nooks and crannies throughout the space for a bit more privacy. Keep going 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. If I had to guess, the performance venue probably fits around 150 people or so pre-covid.  A lot 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 – $20, which is not a bad price to pay to potentially watch an up-and-coming superstar.