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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
After nearly two decades of investing in and managing Chicago real estate, I’ve had the privilege of working in almost every pocket of the city. And while each neighborhood has its own strengths, one always rises to the top for me—Lakeview. As a property manager, investor, and someone who has watched the city evolve block by block, Lakeview stands out as one of the most dynamic, stable, and opportunity-rich areas on the North Side.
Whether you’re a small landlord, a first-time investor, or someone thinking about renting out your current home, Lakeview offers a combination of demand, livability, versatility, and long-term upside that is hard to match anywhere else in Chicago.
Here are the three big reasons why managing rentals in Lakeview is my favorite.
1. A Thriving, Transformed Neighborhood Built Around Community, Entertainment & Convenience
If you haven’t spent time in Lakeview recently, you may not realize just how dramatic the transformation has been, especially around Wrigley Field and the Southport Corridor. These two redevelopment engines have completely elevated the area and created a true live-work-play environment that attracts residents from all walks of life.
The Wrigleyville Evolution
The changes around Wrigley Field over the last decade are nothing short of remarkable. What used to be a neighborhood centered almost exclusively around game day crowds has turned into a year-round destination with restaurants, retail, entertainment, and family-friendly attractions.
Note: As a property manager the one downside is when you have to complete WOs and moving your maintenance team around easily on game day or event nights!
The addition of Gallagher Way has made Wrigleyville more than a baseball district. It’s now a community gathering spot with outdoor movies, farmers markets, ice skating, concerts, and neighborhood events. For landlords and property owners, these amenities drive consistent demand—and not just from Cubs fans.
The Southport Corridor Boom
Meanwhile, Southport Corridor has grown into one of Chicago’s most desirable retail and residential streets. Its combination of boutique shopping, high-quality dining, walkability, and access to transit appeals equally to young professionals, families, and long-time Chicagoans.
The redevelopment and reinvestment in these areas has created:
Stronger retail corridors
More stable tenant demand
A safer, more vibrant neighborhood feel
Broad appeal across age groups
This stability is exactly what investors crave. When you own property in a neighborhood that continues to improve, you benefit not just from cash flow today, but also appreciation over time. As a property manager, Lakeview is one of the easiest areas to consistently place strong tenants because the neighborhood truly sells itself.
2. A Neighborhood That Attracts Investors From Every Background
One of my favorite things about working in Lakeview is seeing the diverse mix of people who are drawn to investing here. You’ll find:
First-time landlords renting out their condo when they move to the suburbs
House hackers using a 2–4 unit to offset their mortgage
Long-term investors buying and holding for wealth building
Newer investors looking for their first “safe” and stable neighborhood
Out-of-state buyers who want a predictable rental market
Experienced multifamily owners adding prime North Side assets to their portfolio
Lakeview pulls from every category because it sits at the intersection of what both landlords and tenants want: strong schools, proximity to transit, access to shopping and nightlife, near-lake access, and stable long-term demand.
From the management perspective, this makes the job easier, and more enjoyable. Investors in Lakeview tend to be thoughtful, engaged, and focused on long-term performance. They know they’re buying into a neighborhood with solid fundamentals, and that allows us to help them strategize for future opportunities rather than just problem-solve today’s issues.
3. Some of Chicago’s Best Housing Stock for Investors & House Hackers
Another huge advantage Lakeview offers is its varied housing stock. Whether you’re looking for an entry point or a higher-end investment, the neighborhood has something for everyone.
Condos and Small Apartments
These properties are perfect for first-time landlords or people looking to rent out their home when they upgrade. Lakeview is full of 1–3 bedroom condos and small apartment units in vintage buildings, mid-rise complexes, and newer construction developments.
These units rent extremely well because tenants value:
Walkability
Character-filled vintage units
Transit access
Safety and cleanliness
Local amenities
For an owner-occupant turning their condo into a rental, Lakeview is one of the least stressful places to take that first leap into becoming a landlord.
2–4 Unit Properties
Lakeview also has an excellent inventory of 2–4 unit buildings, making it a prime destination for house hackers and investors building a portfolio of small multifamily properties.
Why House Hacking Works So Well in Lakeview
House hacking—living in one unit of a multi-unit building while renting out the others—is one of the single best ways to get into real estate investing with minimal risk. The rental income helps offset or even cover your mortgage payment, allowing you to build wealth faster.
Lakeview is especially ideal for house hacking because:
Rents are high and stable
Tenant demand is constant
Units lease quickly with minimal vacancy
The neighborhood is safe and appealing to young professionals
Appreciation potential is strong
The lifestyle appeal (restaurants, transit, proximity to the lake) is a major draw
House hackers often stay for a few years and then move on to their next property, turning their first building into a long-term rental. Many of the most successful investors I know in Chicago started this way, and Lakeview is one of the best neighborhoods to execute that strategy.
Should You Rent Or Sell Your Place In Lakeview?
From the continued transformation of Wrigley Field and the Southport Corridor, to its wide appeal among investors, to the incredibly strong and versatile housing stock, Lakeview has consistently proven itself as one of the best neighborhoods in Chicago for rental property owners.
For property managers like me, it’s a dream to work in a neighborhood that has:
Stable demand
Engaged investors
High-quality tenants
Strong appreciation fundamentals
A community that keeps improving
If you’re a small landlord or you’re thinking about moving out of your Lakeview home and turning it into a rental, now is a great time to explore your options.
Who Is On Your Team?
We’ve shared a lot of information here on investing in real estate locally in Chicagoland. If you live outside the area, it may seem overwhelming for those wanting to invest in the Chicago market. But we just look at it as a team sport.
Who’s on your investing team? Do you even have a team? GC Realty & Development, LLC has a dedicated team of professionals willing to share decades of experience in all facets of real estate investment. We handle everything from brokerage, leasing, and property management. Whether you hire us or not, we’re happy to provide our resources and expertise.
What gets me up in the morning and keeps me going 12 hours a day is the ability to add value to local area investors in Chicago and beyond! Those who connect with me often hear me say that our goal is to bring value to everyone we come in contact with.
We hope that in return, they will one day hire us for our tenant placement or property management services, refer us to someone they know, or leave a review about our services. We would clearly love all three; however, we’re happy whenever we get the opportunity to help!
Reach out today!
Partner / Co-Host of Straight Up Chicago Investor Podcast
