The Dakin Estate: 4BR Speakeasy | Walk to Wrigley

Step into the ultimate Art Deco Jazz sanctuary, where Modern Speakeasy Noir meets the high-energy heartbeat of Wrigleyville. Located just a 5-minute stroll from the iconic Wrigley Field, this rare two-level estate is more than just a place to stay—it's a curated experience for those who appreciate sophisticated design and ultimate entertainment. Whether you’re here for the Cubs, a world-class concert, or a deep dive into Chicago’s vibrant nightlife, you’ve found the Vanguard level of luxury.

We want you to feel right at home. While we give guests full privacy, we’re always just a message away if you need anything — from quick answers to local recommendations. If we’re available, we’re happy to assist in person. Our goal is to make your stay smooth, comfortable, and 5-star worthy.

The Epicenter of Entertainment

You are exactly 5 minutes from Wrigley Field, the second-oldest ballpark in the country and a cathedral of American sports history. But the energy doesn't stop at the ninth inning. Gallagher Way, the open-air plaza next to the stadium, hosts year-round events from outdoor movie nights and farmers markets to the enchanting Winterland festival.

A Culinary & Nightlife Playground
Wrigleyville’s dining scene has evolved into a sophisticated playground.

The Classics: Iconic spots like Murphy’s Bleachers and The Cubby Bear offer that authentic, high-octane Chicago game-day atmosphere.

Modern Speakeasy Vibes: For a more "Urban Luxe" experience, explore the hidden cocktail dens and elevated eateries on Clark and Addison. You are steps away from some of the city's best award-winning BBQ, authentic taco joints, and upscale sushi.

Unbeatable Connectivity
One of the most strategic advantages of this location is the 2-minute walk to the CTA Red Line.

Downtown Access: You can be at the Magnificent Mile or the Loop in under 12 minutes, making world-class shopping and the Theatre District easily accessible.

Lakefront Proximity: You are a short walk or bike ride from Lake Michigan and the Lakefront Trail, offering miles of scenic paths for your morning 30-30-30 routine.

Beach Access: You are a short 8-Minute drive or 10-Minute bike ride from the nearest beach.

The "Steal" of the Neighborhood

In a neighborhood where parking is notoriously difficult and expensive, having your dedicated onsite parking space is a true mogul move. It gives you the freedom to explore the wider city or commute to suburban business hubs without ever worrying about a spot.

The Walkability Factor

Everything your guests need is within a short, scenic stroll.

Wrigley Field (Home of the Cubs): * 0.2 Miles | 4-Minute Walk

Steps away from the action, but just far enough to escape the post-game crowds.

Sheridan CTA Red Line Station:

0.3 Miles | 2-Minute Walk

Your gateway to the entire city.

Right in the heart of the Clark Street entertainment corridor.

Lake Michigan & Lakefront Trail:

0.7 Miles | 15-Minute Walk

Perfect for a morning run or a peaceful sunset by the water.

City Connectivity

For guests looking to explore beyond the neighborhood.

The Magnificent Mile (High-End Shopping):

4.5 Miles | 12-Minute Drive (via DuSable Lake Shore Drive)

18 Minutes via CTA Red Line.

The Loop (Downtown Business District):

5.5 Miles | 12-Minute Drive (Off-peak)

22 Minutes via CTA Red Line.

Fulton Market (Dining Mecca):

6.2 Miles | 18-Minute Drive

The best of Chicago’s culinary scene is just a quick Uber away.

Guests will have private access to the entire first-floor flat, lower level flat, including 4 bedrooms, 2 bathrooms, living and dining areas, a full kitchen, and the Speakeasy den/lounge.

Keyless Entry
The home is equipped with a keyless lock system for convenient check-in.
You will be provided with one unique code.
Your code will remain active for the full duration of your stay.

Parking
One onsite garage parking included in your stay
Street Permits available for 1 car , any additional cars would be $10/day. Please note Zone 383 permits do not guarantee a spot due to Wrigleyville demand.

If you need anything during your stay, feel free to reach out — we’re here to help make it smooth and enjoyable!

Upper Level: The Social Hub

The ground floor is designed for high-energy gatherings and features the primary sleeping quarters.

Bedroom 1: The Master King Suite
The Vibe: A spacious, "Urban Luxe" retreat featuring a King-sized bed with premium linens
Layout: Flooded with natural light from the bay windows. This room features a sleek office/vanity nook. Equipped with a chic mid-century chair and desk, it serves as the perfect executive workspace by day and a high-end glam station by night—ensuring you stay productive and camera-ready for the city.


Bedroom 2: The Double Queen Suite
The Vibe: Perfect for groups, this oversized room features two Queen beds.
Layout: Positioned near the kitchen and the full upper-level bath, making it convenient for the morning rush.

Lower Level: The Speakeasy Den

Descend into the moody, "Speakeasy Noir" lower level where the entertainment lives

Bedroom 3: The Garden Queen
The Vibe: A cozy, quiet sanctuary featuring a Queen-sized bed and Art Deco accents.
Layout: Located just off the Speakeasy Den, it offers direct access to the fireplace and pool table area.

Bedroom 4: The Hidden Queen
The Vibe: Tucked away for maximum privacy, this room features a Queen-sized bed.
Layout: Situated next to the lower-level full bath, the addition of the office/vanity chair completes the "hotel-within-a-home" feel—giving guests a completely self-contained space to work, prep, and play just steps from the late-night entertainment.

Navigating the city from this expertly designed retreat is effortless. You are positioned a 2-minute walk from the Sheridan Red Line, offering direct, 24/7 access to the Loop, River North, and the Magnificent Mile. For those preferring to stay local, the celebrated dining of Wrigleyville and Boystown/North Halsted is entirely walkable.

The Epicenter of Entertainment

You are exactly 5 minutes from Wrigley Field, the second-oldest ballpark in the country and a cathedral of American sports history. But the energy doesn't stop at the ninth inning. Gallagher Way, the open-air plaza next to the stadium, hosts year-round events from outdoor movie nights and farmers markets to the enchanting Winterland festival.

A Culinary & Nightlife Playground
Wrigleyville’s dining scene has evolved into a sophisticated playground.

The Classics: Iconic spots like Murphy’s Bleachers and The Cubby Bear offer that authentic, high-octane Chicago game-day atmosphere.

Modern Speakeasy Vibes: For a more "Urban Luxe" experience, explore the hidden cocktail dens and elevated eateries on Clark and Addison. You are steps away from some of the city's best award-winning BBQ, authentic taco joints, and upscale sushi.

Unbeatable Connectivity
One of the most strategic advantages of this location is the 2-minute walk to the CTA Red Line.

Downtown Access: You can be at the Magnificent Mile or the Loop in under 12 minutes, making world-class shopping and the Theatre District easily accessible.

Lakefront Proximity: You are a short walk or bike ride from Lake Michigan and the Lakefront Trail, offering miles of scenic paths for your morning 30-30-30 routine.

Beach Access: You are a short 8-Minute drive or 10-Minute bike ride from the nearest beach.

The "Steal" of the Neighborhood

In a neighborhood where parking is notoriously difficult and expensive, having your dedicated onsite parking space is a true mogul move. It gives you the freedom to explore the wider city or commute to suburban business hubs without ever worrying about a spot.

The Walkability Factor

Everything your guests need is within a short, scenic stroll.

Wrigley Field (Home of the Cubs): * 0.2 Miles | 4-Minute Walk

Steps away from the action, but just far enough to escape the post-game crowds.

Sheridan CTA Red Line Station:

0.3 Miles | 2-Minute Walk

Your gateway to the entire city.

Right in the heart of the Clark Street entertainment corridor.

Lake Michigan & Lakefront Trail:

0.7 Miles | 15-Minute Walk

Perfect for a morning run or a peaceful sunset by the water.

City Connectivity

For guests looking to explore beyond the neighborhood.

The Magnificent Mile (High-End Shopping):

4.5 Miles | 12-Minute Drive (via DuSable Lake Shore Drive)

18 Minutes via CTA Red Line.

The Loop (Downtown Business District):

5.5 Miles | 12-Minute Drive (Off-peak)

22 Minutes via CTA Red Line.

Fulton Market (Dining Mecca):

6.2 Miles | 18-Minute Drive

The best of Chicago’s culinary scene is just a quick Uber away.