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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
When you spend more than two decades managing properties in a neighborhood, you develop a perspective that goes far deeper than market reports or MLS data. I’ve been on the ground in Avondale for over 20 years, long before it became a neighborhood investors talked about on podcasts, and long before people started using words like “emerging” or “hot.” In that time, I’ve managed dozens of buildings on both sides of the highway, walked these streets through multiple market cycles, and watched tenants, owners, and investors reshape the fabric of the community.
As the co-host of the Straight Up Chicago Investor podcast, I talk to investors every week about what’s working in Chicago and where the next opportunities lie. And I can say confidently, with both my boots-on-the-ground experience and wide-lens market perspective, that Avondale is one of the strongest opportunities in Chicago right now. Whether you’re a first-time house hacker, an investor expanding your portfolio, or a current homeowner wondering if now is the time to convert your property into a rental, Avondale deserves your attention.
Let me break down why.
The First and Biggest Opportunity: West Avondale Near Irving Park
Avondale isn’t a monolithic neighborhood. The experience, the tenant base, and even the investment outcomes can change dramatically from one pocket to another. And after 20 years managing on both sides of the highway, I can tell you with certainty: the biggest investment opportunity today lies on the west side of Avondale, particularly as you move north toward Irving Park.
For years, that part of the neighborhood lagged behind the east side in terms of development and demand. Most investors overlooked it, preferring to stay closer to Logan Square’s border or along the more established strips. But neighborhoods evolve, sometimes quietly, sometimes all at once, and west Avondale has been experiencing both types of transformation.
I’ve watched tenants who once insisted on Logan Square or Roscoe Village become increasingly open to Avondale because they recognize the value. And now that demand is spreading westward, investors have a window of opportunity. Properties in these pockets still trade at more accessible entry points, particularly compared to the neighborhoods immediately to the south and west.
For house hackers specifically, this is the sweet spot. You can still find buildings where the math works, even as other neighborhoods have priced many beginners out. And as someone who's seen hundreds of these situations play out over the years, opportunities like this don’t usually stay available for long.
Inventory That House Hackers Can Still Make Work
Let’s talk directly to the first-time house hackers for a moment, because you are the group that stands to gain the most from Avondale’s current phase.
One of the biggest challenges in today’s market is finding neighborhoods where both the acquisition price and rental income support a house hack, especially when interest rates have created tighter margins across the board. In many of the commonly targeted neighborhoods, the numbers have simply gotten too tight.
Not in Avondale.
Even with the neighborhood’s growth, Avondale continues to offer inventory at price points that make a house hack not just possible but strategically smart. The combination of manageable purchase prices and strong tenant demand creates an environment where a well-selected two-flat or three-flat can still meaningfully offset your living expenses.
Over the years, I’ve watched countless house hackers buy in Avondale and set themselves up for long-term success. What’s changed today isn’t the opportunity, it’s the level of awareness. More investors are waking up to what this neighborhood offers, which means you’re competing with not just first-time buyers but experienced investors who also see the upside.
That doesn’t mean you should rush in blindly. It means you should consider Avondale seriously, and run the numbers with someone who understands the micro-markets, block-by-block trends, and tenant profiles.
Rents With Room to Grow, Especially Relative to Neighboring Hotspots
The rent story in Avondale is one I’ve lived in real time. I’ve leased units in this neighborhood through three different market cycles, and one thing that consistently surprises newer investors is how much room Avondale still has for rental growth.
Here’s the reality from a property manager’s perspective:
Logan Square, Wicker Park, Roscoe Village, and Ukrainian Village have all experienced substantial rental appreciation over the past decade.
Renters priced out of those areas increasingly look to Avondale for similar character, amenities, and transit access, but at a better value.
Avondale rents remain relatively accessible, creating a runway for continued growth that simply isn’t available in some of the more saturated neighborhoods.
This is exactly the type of rent trend experienced investors look for: pressure from more expensive neighbors + increasing demand from quality tenants + room to grow without overshooting the market.
And from my leasing experience, it’s clear that tenants don’t just see Avondale as an “alternative”, many now see it as a preferred choice, especially those who want the Logan Square vibe without the Logan Square price tag.
Why Current Avondale Homeowners Are in a Unique Position
Now, for the group that sometimes doesn’t realize how strong their position is: current Avondale homeowners.
If you bought your property anytime in the last 10 years, there’s a good chance you locked in a very favorable interest rate. Combine that with the appreciation the neighborhood has experienced, and you’re sitting on an asset that can cash flow far better than it could have when you first bought it.
This is one of the most overlooked investment opportunities in Chicago right now. I talk to Avondale homeowners all the time who are considering a move and assume they should sell. But when we run the numbers, converting their home into a rental often becomes the smarter long-term play, especially given where rents are heading and how their financing positions them.
And because GC Realty & Development has managed dozens of these conversions firsthand, we know exactly what works, where the pitfalls are, and how to maximize the upside while minimizing headaches.
Proximity to the Blue Line: A Non-Negotiable Advantage
If there’s one consistent lesson I’ve learned over 20 years managing in Avondale, it’s this:
Transit access, especially the Blue Line, makes or breaks rental performance.
Being close to the Belmont, Addison, or Irving Park stops does three things for an investment property:
Attracts a wider and more reliable tenant pool
Keeps occupancy high during softer market periods
Supports long-term rent growth
Some investors underestimate how powerful transit adjacency is. I’ve leased the same buildings multiple times over multiple cycles, and the Blue Line-proximate units always perform better, even during downturns.
So whether you’re house hacking or buying your fifth building, prioritize proximity to the Blue Line. It’s one of the few variables that has consistently delivered ROI regardless of market conditions.
Why GC Realty & Development Knows This Market Better Than Anyone
GC Realty & Development has been managing in Avondale almost as long as I’ve been working in the neighborhood. As a team, we’ve seen Avondale through:
the early 2000s investment wave
the post-recession stabilization
the slow, steady rise through the mid-2010s
the recent acceleration of demand
This is the type of experience that simply can’t be replicated by looking at comps or online data. When we advise investors, whether they’re house hackers, seasoned buyers, or homeowners considering conversion, we’re drawing from real operational history: tenant behavior, rent trends, renovation ROI, leasing challenges, turnover patterns, and building-level nuances.
This depth of knowledge is exactly what helps investors avoid costly mistakes and capture real upside in Avondale’s evolving market.
Why Now Is the Time to Invest in Avondale
Avondale is in the middle of a rare alignment:
Accessible inventory for house hackers
Strong rent demand with clear room for growth
Current homeowners sitting on ideal conversion conditions
Long-term neighborhood momentum that hasn’t fully peaked
Transit access and west-side value that provide a built-in hedge
A 20-year track record of property management data that supports all of the above
From where I sit, as a property manager who’s been inside more Avondale units than most investors will ever see and as a podcast host constantly analyzing Chicago’s micro-markets, this is one of the clearest opportunities in the city right now.
If you’re evaluating a house hack, growing your portfolio, or even just wondering whether to hold onto your current property, Avondale deserves to be at the top of your list.
And if you want the guidance that comes from decades of real experience in this neighborhood, GC Realty & Development is here to help you make the most of it.
Don’t Want To Go At This Alone?
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 really 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
