The Run Down

Walking through Chicago's Gold Coast neighborhood is the like the real life version of scrolling through Zillow and daydreaming about the type of place you'd buy once that dogecoin investment comes through. It's dotted with historic mansions and beautiful row homes that make this not only the most expensive neighborhood in Chicago, but also the seventh richest urban neighborhood in the United States. While you can expect to find the usual clusters of high end retail stores, fashion brands, and fine dining options, we've got other plans in mind. For this guide we've got a classic date night that starts at a small, intimate Italian restaurant for shared plates of burrata. Afterwards, you'll head down the street to a 1940's, Cuban-inspired cocktail bar to end the night.

1. Small Plates @ Eduardo's Enoteca

2. Rum Cocktails @ Sparrow

1. Eduardo’s Enoteca

We’re starting off date night in the middle of all the action in Gold Coast. On one end of the neighborhood spectrum, you have your  collection of high end restaurants lined up on Rush Street. On the other end, you have a bevvy of late night bar spots on Division St.

Falling into the much needed middle of the spectrum is Eduardo’s Enoteca. This is a small Italian eatery that’s become a beloved spot with locals in the neighborhood looking for a casual spot for cocktails, wine, and small plates.

Eduardo’s is located just off to the side of a busy commercial corridor, and  it’s situated on a street full of beautiful row homes and high rises that have come to embody this neighborhood. Take a step inside and you’ll find a narrow dining room with about ten tables, which was just about right to make for an intimate experience but not too tight either. Here are a few other logistics notes.

– You can usually get a table pretty quickly, even at the busiest hours on the weekend.

– If you want to plan ahead, they take reservations and you can usually book some decent times even the day of.

– Like most restaurants, Eduardo’s has put a lot of work to improve their sidewalk patio seating. They have a covered tent with lots of high capacity heaters.

Let’s talk food. This place is known for their variety of small plates and artisan pizzas. Pictured below is a representative example of their small plate offerings.

At the top is a plate of arancini — risotto balls mixed with parmesan that’s then coated in breadcrumbs and deep fried. Let’s pause to thank the 10th-century Sicilians who invented this delicious culinary work of art.

If you’re looking for other small plate recommendations, this burrata doused in herb pesto was also a major winner. It’s accompanied by thick slices of focaccia bread, which served as a fine delivery vehicle to scoop up our cheese.

For the main course, their artisan pizzas are perhaps the stars of the show. In terms of size, they’re fit to share between two, maybe three people. It’s well balanced and you get the type of crunch you’d expect from a well made thin crust pizza.

2. Sparrow

If the date is going well, you’re just a few blocks from our next spot. We’re headed to Sparrow, a Cuban-inspired bar concept with an art deco flair that looks like it’s been ripped right from the Great Gatsby. The entrance to the bar is at the ground floor of a mid-rise apartment building that dates back to 1927. Here are a few notes as you plan your visit.

– Open Mon-Fri until 2am and Saturday until 3am.
– Check in with the host up front. It’s first come, first served. No reservations.
– Servers will bring out water, but you order everything else at the bar.

As you walk in you’ll find yourself facing this long narrow bar with the bartenders working furiously to concoct a number of different rum cocktails that Sparrow has curated and made a central part of their menu.

At first the space seems a bit small, but once you look around, you’ll find small pockets of seating that give you a lot more room to spread out.

12This nook at the front of the bar is perhaps our favorite spot in the place.  The neon sign and fern overhead completes our immersive transportation back to 1940s Havana.

Head towards the back and there’s an even bigger seating area.

If you need more convincing that this will work as a great date night spot, I submit this picture below. Every single person in the picture is coupled up. You know what happened to each of them? They all got married and lived happily ever after.