The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

The Dakin Estate is a refined two-level 4BR Art Deco duplex in Wrigleyville, blending elevated design, comfort, and entertainment just minutes from Wrigley Field. The home features a stylish main level with a full kitchen, dining area, and spacious suites, plus a private speakeasy lounge with a pool table, and dedicated gathering space. Includes 2 baths, WiFi, laundry, patio, garage parking, and permits.

Your comfort and privacy are our priority. You’ll have full access to The Dakin Estate throughout your stay, while our local hospitality team remains just a message away whenever you need assistance.

Whether you need recommendations for Wrigleyville dining, local attractions, or help with anything during your visit, we’re here to make your experience seamless and stress-free. If additional assistance is needed and our schedule allows, we’re happy to help personally.

Our goal is simple: provide thoughtful, responsive hospitality while giving you the freedom to enjoy Chicago your way.

The Dakin Estate places you in the heart of Wrigleyville, just minutes from Wrigley Field and one of Chicago’s most iconic entertainment districts. Beyond game days, the neighborhood stays vibrant year-round with concerts, festivals, outdoor events, and local experiences at Gallagher Way.

Wrigleyville offers a unique mix of classic Chicago traditions and modern dining. Walk to legendary game-day destinations like Murphy’s Bleachers and The Cubby Bear, or explore Clark Street’s restaurants, cocktail bars, craft breweries, elevated dining, and local favorites.

The location also offers effortless access to the rest of Chicago. The CTA Red Line is just a short walk away, connecting you directly to downtown, River North, the Magnificent Mile, and beyond.

Guests enjoy exclusive access to the entire first-floor and lower-level duplex, including four bedrooms, two bathrooms, a full kitchen, living and dining spaces, and the private speakeasy lounge. The entire residence is yours to enjoy with no shared interior spaces.

Secure keyless entry provides a simple and convenient self check-in experience. A personalized access code will be provided before arrival and will remain active throughout your stay, allowing you to come and go on your own schedule.

Need additional sleeping space?

We also offer two twin rollaway beds upon request, making the home ideal for larger families or groups.


Parking:
• 1 onsite garage parking space included
• 1 complimentary street parking permit included (Zone 383)
• Additional permits available for $10/day when available

Our team is always just a message away should you need assistance during your stay. We’re here to provide responsive hospitality while giving you the privacy and flexibility to enjoy Chicago at your own pace.

The Dakin Estate is thoughtfully designed across two levels, balancing elevated comfort, private retreats, and entertainment-focused spaces for unforgettable Chicago stays.

Upper Level: The Social Hub
The main level is designed for connection, featuring the primary gathering spaces and two inviting bedrooms.

The Master King Suite
A refined retreat featuring a king bed, premium linens, abundant natural light from bay windows, and a dedicated office/vanity nook that functions as both a workspace and getting-ready station.

The Double Queen Suite
A spacious group-friendly bedroom with two queen beds, offering comfortable accommodations and convenient access to the kitchen and upper-level bathroom.

Lower Level: The Speakeasy Den
A private entertainment space designed for relaxing evenings, featuring a moody Art Deco atmosphere, lounge seating, and a pool table for group gatherings.

The Garden Queen
A quiet queen bedroom located just off the Speakeasy Den, offering privacy while keeping guests close to the entertainment space.

The Hidden Queen
A secluded queen bedroom with a dedicated office/vanity setup and convenient access to the lower-level bathroom, creating a private suite-like experience.

Across both levels, The Dakin Estate blends social spaces with comfortable private accommodations, making it ideal for groups looking to gather, explore Chicago, and unwind together.

Exploring Chicago from The Dakin Estate is simple and convenient. Located just a short walk from the CTA Red Line, guests have direct 24/7 access to downtown Chicago, the Loop, River North, the Magnificent Mile, and many of the city’s top attractions.

For guests staying local, Wrigleyville and North Halsted offer some of Chicago’s best dining, nightlife, entertainment, and neighborhood experiences—all within easy walking distance.

With exceptional transit access, a highly walkable location, and nearby rideshare options, The Dakin Estate makes it easy to experience Chicago without the hassle of navigating the city by car.

Location Highlights:
• Wrigley Field – ~4–5 min walk
• CTA Red Line (Sheridan Station) – ~2 min walk
• Clark Street restaurants & nightlife – steps away
• North Halsted dining & entertainment – short walk
• Downtown Chicago / The Loop – ~15–20 min via CTA

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.