Hollywood House Apartments in Chicago, IL

Pros

• The location is great and offers plenty to do.
• The staff is great.
• Prospective residents can't wait to move in.
• The building is very clean, and the staff are professional and approachable.
• The apartments are roomy and airy, suited for a young couple or a single person.
• Incredibly nice people live here, and the apartments are very nice for seniors.
• Visitors are impressed by the friendly receptionist and the well-kept apartments.
• The lobby is clean, the patio area is awesome, and residents seem friendly.
• The location near the lake and public transportation makes visits quick, and the building is clean, friendly, and safe.
• It is considered the best place to live.

Cons

• The intercom system has not worked for three years.
• Pipes have burst and flooded the front lobby.
• Habitat Company has been slow to answer tenants' concerns.
• There is now one working elevator that may not be fixed for over two months.
• Heartland Housing has money problems and cannot adequately support Hollywood House and its properties.
• Heartland has been mismanaging federal funds since 2021 earmarked for Hollywood House.
• The city has launched a full-scale review of Hollywood House.
• This has been a horror show for the residents.
• The building has bed bugs.
• Management sucks.

Review

Hollywood House Apartments is best suited for seniors 62 and older who want an active, city-centered lifestyle with easy access to Lake Shore Drive, public transit, and the surrounding amenities of Chicago’s lakefront. The community works best for those who value a friendly, social atmosphere and a lower-cost option in a well-connected neighborhood. It is a pragmatic choice for residents who can tolerate intermittent maintenance hiccups and questions about building management, provided the social fabric, safety feel, and convenient location remain primary motivators. For prospective renters who insist on absolute reliability in security, elevator access, and stable ownership, it is prudent to consider alternatives before committing.

The strongest positives center on location and the social texture of the building. Residents consistently note the landmark appeal of being across from the lake, with plentiful activities nearby and convenient access to transportation. The lobby and common areas often feel welcoming, and several staff members are described as professional, approachable, and friendly, contributing to a sense of community that many seniors find essential. Apartments themselves are described as roomy and airy, making the space comfortable for longer stays or for hosting visitors. The overall vibe, an affable, senior-centered environment, buoys the experience, especially for those who prioritize connection and ease of access over pristine operational control.

Yet the most consequential drawbacks are hard to overlook. The longstanding security and maintenance gaps pose real risks: intercoms that have not functioned properly for years, and an absence of reliable security measures that has left residents feeling exposed. Infrastructure problems, pipes bursting and flooding the entry, with slow contractor response, compound concerns about daily safety. An elevator situation compounds the risk for mobility-impaired residents or those who need to coordinate medical visits, groceries, and social activities around limited vertical access. Financial uncertainties around Heartland Housing, reports of funds being diverted or mismanaged, and a potential sale of the property inject a sense of instability that colors every practical decision, from maintenance schedules to long-term planning.

Those pros can mitigate some downsides for certain buyers, but the offset is partial and contextual. For independent seniors who prize location, a welcoming community, and affordable rents, the draws can outweigh the negative headlines if the building’s social environment remains robust and the elevator is occasionally usable. The presence of a 24-hour security mentality and a visible, friendly staff in the public areas can deliver daily confidence that compensates modestly for occasional service lapses. In other words, the overall appeal hinges on whether the resident can tolerate disruption while prioritizing social life and proximity over dependable infrastructure and predictable operations.

Explicitly, this property may not be the right fit for those who require unwavering reliability or who cannot manage the risk of ownership changes and maintenance delays. Bed bug concerns surfaced in several reviews, and while not universal, they underscore the importance of a thorough inspection and documented remediation history before move-in. Parking costs, occasional high convenience fees, and the mixed message about long-term ownership further suggest that the value proposition rests on personal risk tolerance and desire for a strong neighborhood microculture rather than on pristine, turnkey operation. Alternatives with steadier management, newer infrastructure, and transparent capital plans will appeal to those who place a premium on predictability.

In the end, Hollywood House Apartments offers a practical, budget-conscious option for seniors who choose social richness and geographic advantage over flawless operations. The decision comes down to personal priorities: embrace a vibrant lakefront commute and a warm resident network, or seek a setting with unwavering elevator service, unambiguous security, and a longer track record of capital investment. Prospective tenants should directly probe the current status of the elevator, intercom, and security measures; demand a candid account of any planned capital improvements; and request recent remediation logs for pest control. If the answer aligns with a tolerance for occasional disruption in exchange for community and proximity, this remains a compelling choice. If not, it is wise to continue the search elsewhere.

This part of Chicago, Illinois, offers a convenient and diverse range of amenities for senior living. With multiple pharmacies such as Walgreens and CVS nearby, easy access to medication and healthcare services is ensured. Additionally, a variety of cafes like Starbucks provide pleasant spots for socializing or enjoying a leisurely cup of coffee. A selection of restaurants offer dining options for every taste, while several parks provide opportunities for outdoor recreation and relaxation. Close proximity to public transportation hubs such as CTA stations make getting around the city straightforward. Nearby hospitals like Swedish Covenant Hospital Cancer Care and Saint Francis Hospital ensure quality medical care is easily accessible. For entertainment, theaters like Regal Webster Place are within reach. Overall, this area combines convenience, healthcare facilities, recreational opportunities, and entertainment options suitable for senior living.

Pharmacies

• Walgreens (0.3 miles)
• Walgreens (0.6 miles)
• CVS Pharmacy (0.6 miles)
• Walgreens (0.7 miles)
• Walgreens (1.3 miles)
• Mariano's Pharmacy (1.5 miles)
• Walgreens (1.5 miles)

Cafes

• Starbucks (0.6 miles)
• Starbucks (1.6 miles)
• Starbucks (2 miles)
• Starbucks (3.1 miles)
• Little Beans Cafe (3.3 miles)
• Starbucks (4.2 miles)
• Starbucks (4.2 miles)

Restaurants

• Little Bad Wolf (0.7 miles)
• SoFo Tap (1.1 miles)
• R Public House (2.2 miles)
• Cell Block (2.5 miles)
• Murphy's Bleachers (2.5 miles)
• Las Mananitas Mexican Restaurant (2.7 miles)
• Hydrate (2.8 miles)

Transportation

• Cta (1.3 miles)
• CTA Jarvis (2.2 miles)
• Cta (2.5 miles)
• Cta (2.6 miles)
• CTA - Belmont (3.2 miles)
• CTA - Fullerton (4.2 miles)
• Cta (5.5 miles)

Parks

• Warren Park (2.1 miles)
• Dubkin Park (2.3 miles)
• Horner Park (2.7 miles)
• Hamlin Park (3.6 miles)
• Wrightwood Park (4 miles)
• Independence Park (4.2 miles)
• Dawes Park (4.3 miles)

Hospitals

• Swedish Covenant Hospital Cancer Care (2.4 miles)
• Saint Francis Hospital (3.1 miles)
• Advocate Illinois Masonic Medical Center (3.4 miles)

Theaters

• Regal Webster Place (4.5 miles)

Physicians

• Lincoln Park Dental Specialists (4.8 miles)
• North Shore Physicians Group (5 miles)