Designer Home | Steps to the Obama Center & Beach

Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine-worthy interiors, featuring dramatic entertaining spaces, bespoke design details, and a chef's kitchen designed for gathering. Crafted for guests who appreciate exceptional homes, this private residence delivers a stay that's as memorable as the city itself.

Stay here. Communication is sharp, support is discreet, and everything just works.

We don’t hover—you get the space to own your stay. Check-in is fully automated, and your privacy is the priority. When you need us, we’re a text away for anything from elite car services to hard-to-get reservations in Wrigleyville and North Halsted. Otherwise, the space is yours. No friction. No noise. Just your stay, exactly how it should be.

Access is seamless, private, and fully controlled.

You’ll have exclusive use of the entire 5 BR home including five bedrooms, 3.5 bathroom, a full kitchen, and a comfortable living area designed for both relaxation and entertainment.

Entry is keyless with a unique access code provided before arrival, allowing for frictionless self check-in at any time. Your code is active for the duration of your stay, ensuring both convenience and security.

On-site shared laundry is available for guest use, and 2 spaces inside of our onsite parking garage.

Everything is designed for privacy, ease, and an elevated stay from the moment you arrive.

The Dorchester offers multiple gathering spaces thoughtfully designed for both entertaining and relaxing. The home features a formal sitting room, designer living room, chef's kitchen, dining room, and several cozy lounge areas throughout the property.

Sleeping Arrangements:
• Bedroom 1: King Bed + Smart TV + Ensuite Master Bath with soaking tub and standing shower.
• Bedroom 2: King Bed + Smart TV
• Bedroom 3: Queen Bed + Smart TV + Ensuite Bathroom with soaking tub.
• Bedroom 4: Queen Bed + Smart TV
• Bedroom 5: Two Twin-Over-Twin Bunk Beds (Sleeps 4) + Smart TV

The chef's kitchen features premium appliances, generous counter space, and seating for gathering over meals and conversation. Throughout the home, guests will find bold designer interiors, curated artwork, historic architectural details, and comfortable spaces to unwind.

Additional amenities include private garage parking, high-speed Wi-Fi, Smart TVs in every bedroom, and ample space for families, groups, graduation weekends, executive retreats, and extended stays.

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: 10:00 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.