Why Renters Choose Old Town & Gold Coast — And What Makes Them Attractive Investment Markets

Shawn Swift
May 29
4 min read

Few Chicago neighborhoods combine historic charm, walkability, luxury amenities, and strong rental demand quite like Old Town and the Gold Coast. Located just north of Downtown Chicago and the Magnificent Mile, these neighboring communities continue to attract a wide range of renters while remaining popular destinations for real estate investors seeking long-term appreciation and stable occupancy.

Whether you're considering purchasing an investment property or evaluating the performance of an existing rental, understanding what drives demand in these neighborhoods can help maximize long-term returns.

Why Renters Love Old Town and Gold Coast

Prime Location

One of the biggest advantages of both neighborhoods is location.

Residents enjoy easy access to:

Downtown Chicago
River North
The Magnificent Mile
Lake Michigan
Lincoln Park
CTA Red, Brown, and Purple Lines

For many renters, the ability to walk to work, restaurants, shopping, nightlife, and the lakefront significantly improves quality of life while reducing commute times.

Easy Access to Downtown Chicago

Another major draw for renters is the ability to reach Downtown Chicago in just minutes. Many residents work in The Loop, River North, Streeterville, or West Loop and appreciate the convenience of a short commute via CTA, bike, rideshare, or even walking. As more employers continue to encourage in-office collaboration, proximity to Downtown remains a significant advantage that helps support long-term rental demand in both Old Town and the Gold Coast.

Dining, Shopping, and Entertainment

The Gold Coast is known for luxury shopping along Oak Street, its proximity to the Magnificent Mile, and some of Chicago's most iconic dining destinations. Residents enjoy easy access to upscale restaurants, boutique shopping, and the vibrant social scene surrounding the well-known Viagra Triangle, a popular gathering spot featuring outdoor cafés, restaurants, bars, and nightlife.

Old Town offers a slightly different atmosphere, blending historic character with a lively neighborhood feel. The Wells Street corridor serves as the heart of the neighborhood, featuring a diverse mix of restaurants, bars, coffee shops, boutiques, and entertainment venues. Residents also enjoy easy access to The Second City, neighborhood festivals, and one of Chicago's most walkable dining and nightlife districts.

Together, Old Town and the Gold Coast offer a unique combination of luxury, convenience, entertainment, and neighborhood charm that continues to attract renters seeking an active urban lifestyle.

Access to Parks and the Lakefront

Both neighborhoods benefit from proximity to some of Chicago's most desirable outdoor amenities, including:

Lincoln Park
North Avenue Beach
Oak Street Beach
The Lakefront Trail

Access to green space and recreation remains a major factor influencing rental demand, particularly among professionals, pet owners, and active residents.

Diverse Renter Base

Old Town and Gold Coast attract:

Young professionals
Corporate relocations
Medical professionals
Empty nesters
Graduate students
Long-term Chicago residents

This broad appeal helps support year-round rental demand and contributes to lower vacancy risk compared to many other neighborhoods.

What Makes a Strong Investment Property in Old Town & Gold Coast?

Not all properties perform equally, even within highly desirable neighborhoods.

Walkability Matters

Properties located near:

CTA stations
Wells Street
Oak Street
North Avenue Beach
Major employment centers often generate stronger renter interest and lease more quickly.

Updated Kitchens and Bathrooms

Today's renters place a premium on modern finishes. Updated kitchens, renovated bathrooms, in-unit laundry, central air, and contemporary finishes frequently command higher rents and shorter vacancy periods.

Outdoor Space

Private balconies, rooftop decks, patios, and shared outdoor amenities continue to be highly desirable features in both neighborhoods.

Parking

Off-street parking remains a significant advantage, particularly in Old Town and the Gold Coast where street parking can be limited.

Evaluate HOA Assessments and Building Condition Carefully

While many condominium buildings in Old Town and the Gold Coast offer attractive amenities and strong rental demand, investors should pay close attention to both monthly HOA assessments and the overall condition of the building.

Many of the high-rise condominium buildings in these neighborhoods were originally constructed in the 1960s and 1970s. While many have been well maintained and updated over the years, others have accumulated deferred maintenance that can eventually result in significant capital projects and special assessments.

Items such as facade repairs, elevator modernization, roof replacements, riser projects, plumbing upgrades, garage repairs, life-safety improvements, and large-scale window replacement projects can lead to substantial costs for unit owners. In many older high-rises, window replacement projects alone can result in special assessments ranging from several thousand to tens of thousands of dollars per unit.

Buildings with extensive amenities such as pools, fitness centers, door staff, valet parking, package receiving, and large common areas often carry significantly higher monthly assessments as well. While these amenities can attract renters and support rental rates, excessive HOA fees can materially impact cash flow and reduce overall investment returns.

Two units with identical rental income can produce dramatically different cash flow results depending on HOA assessments, reserve health, and the likelihood of future special assessments. Reviewing reserve studies, financial statements, board meeting minutes, and the association's history of special assessments is often just as important as evaluating the unit itself.

For many investors, the best opportunities are found in buildings that strike a balance between desirable amenities and strong financial health—without excessive assessments or significant deferred maintenance that could negatively impact future returns.

Investment Outlook

Old Town and the Gold Coast continue to benefit from limited available land, strong neighborhood identities, and consistent renter demand. While acquisition costs are often higher than many Chicago neighborhoods, investors are frequently attracted by:

Stable occupancy
Premium rental pricing
Long-term appreciation potential
Broad renter appeal
Strong resale demand

For many owners, these neighborhoods offer a compelling combination of income generation and long-term wealth preservation.

How City Roots Properties Helps Owners Succeed

At City Roots Properties, we help Chicago property owners maximize rental performance through strategic pricing, professional marketing, tenant screening, maintenance coordination, and responsive communication.

Whether you own a condo, townhome, or multi-unit investment property in Old Town or the Gold Coast, we can help you understand current rental market conditions and develop a strategy to maximize returns.