Welcome to the Wrigleyville Art Deco Executive Duplex, a spacious 5-bedroom, two-story retreat designed for memorable group stays. Just steps from Wrigley Field, the home features two fully equipped kitchens, a designer poker room, foosball lounge, private patio with fire pit, and garage parking. Walk to the restaurants, bars, and nightlife of Wrigleyville and North Halsted while enjoying the comfort of a private home.

Your privacy is important to us, and you'll have exclusive use of the entire duplex throughout your stay. If anything comes up, our local team is always within reach and happy to assist with recommendations, special requests, or questions about the home.

Our goal is simple: provide thoughtful, responsive hospitality that allows you to enjoy a seamless stay from arrival to departure.

I prefer the second version for your luxury portfolio. It feels more like a boutique hotel concierge experience and less like a typical Airbnb host, which aligns well with the Vanguard Elite Management brand.

Experience one of Chicago's most iconic neighborhoods from the heart of Wrigleyville. Located just steps from Wrigley Field, you'll be surrounded by renowned restaurants, lively cocktail bars, neighborhood cafés, and year-round entertainment. A short walk south brings you to North Halsted, one of Chicago's most celebrated dining and nightlife districts, known for its welcoming atmosphere, live entertainment, and vibrant local culture. Whether you're visiting for a Cubs game, concert, weekend getaway, or to explore the city, you'll enjoy one of Chicago's most walkable and energetic neighborhoods.

The Addison Duplex provides an entirely private, multi-level residential experience. Guests have exclusive command of both the primary executive level and the connected lower-level sanctuary. This 5-bedroom floor plan encompasses two full culinary suites, a professional poker gallery, and a private outdoor fire-lit terrace.

Access is managed via an encrypted keyless entry system through the primary residence entrance, with an internal staircase providing secure movement between levels. Situated at the nexus of Wrigleyville and the Boystown/North Halsted cultural district, this duplex is a self-contained sanctuary. Secure on-site garage parking and additional street permit support are included as standard.

"Designed for larger groups, the Wrigleyville Art Deco Executive Duplex offers 2,800 square feet of living space across two private levels, giving everyone room to gather, relax, and spread out. Connected by a private interior staircase, the home's layout balances inviting shared spaces with comfortable private retreats.

Main Level
The upper level is the heart of the home, featuring spacious living and dining areas, a fully equipped kitchen, and comfortable gathering spaces for meals, conversation, or planning your next Chicago adventure.

Lower Level
The lower level is designed for entertaining, with a dedicated poker lounge, professional foosball table, additional living space, and a second fully equipped kitchen, making it easy for larger groups to enjoy time together.

Bedrooms
Five thoughtfully appointed bedrooms are spread across both floors, offering a mix of privacy and convenience for families, friends, and group travelers.

Outdoor Living
Step outside to your private patio with a fire pit, an inviting space to enjoy morning coffee, evening cocktails, or unwind after a day exploring the city."

The Addison Duplex offers superior transit logistics for the discerning group. Situated a 1-minute walk from the Wrigley Field landmark and a 3-minute walk from the CTA Red Line, the residence provides an efficient link to Chicago’s primary business and entertainment districts. The walkable layout of the surrounding Boystown/North Halsted cultural corridor ensures that premier culinary destinations are accessible within minutes.

For guests traveling via private vehicle, the duplex includes exclusive parking provisions: one secure on-site garage space and one complimentary street permit. Taxis and executive transit options circulate the area with high frequency, providing professional-grade mobility throughout your stay.

Nearby Highlights

Wrigley Field: 1-minute walk
Gallagher Way: 1-minute walk
Addison Red Line Station: 3-minute walk
Lakefront Trail: 10-minute walk
Downtown Chicago: Approximately 20 minutes by train or car

We’re excited to host you and want to ensure your stay is comfortable, enjoyable, and stress-free. To help make that happen, please review the rules below.

General Rules

No Smoking Indoors: Smoking and vaping are strictly prohibited inside the property. Outdoor smoking is permitted in designated areas. Violations will result in a $500 fine.

No Parties or Events: Parties, events, or unregistered overnight guests are not allowed. Violations may result in immediate cancellation and fines of up to $750.

Quiet Hours: 10:00 PM – 7:00 AM. Three verified noise complaints from neighbors may result in a $300 fine.

Check-In & Check-Out

Check-In: Begins at 4:00 PM. Early check-in before 2:00 PM may be available with approval and rush cleaning fee.

Check-Out: 11:00 AM. Late check-outs require prior approval; unapproved late check-outs may incur a full-night charge.

Damage & Maintenance

Please report any cleaning concerns, damages, or issues within 24 hours of arrival. Prompt reporting allows us to resolve issues quickly. Failure to report may result in fees if damages are later found.