Key takeaways:
- VA loans work well in Old Town, but condo purchases require VA approval of the building — not just the unit — which eliminates a meaningful portion of the available inventory.
- Old Town skews heavily toward condos and townhomes, so veteran buyers need to know which property types VA financing covers before they start touring.
- Getting your Certificate of Eligibility and a VA-experienced lender locked in before you search is the move that separates competitive VA buyers from frustrated ones.
- Working with an agent who knows which Old Town buildings are already VA-approved saves time and prevents falling for a unit you cannot finance.
VA loan buyers can absolutely purchase a home in Old Town — but the neighborhood's condo-dominant inventory means your first priority is identifying which buildings are already VA-approved. For detached homes and townhomes, VA financing is more straightforward. For condos, which make up the bulk of Old Town's market, the entire building must be on the VA's approved list or go through a spot-approval process, and not every building qualifies. Knowing that going in changes how you search.
Old Town sits just north of downtown Chicago, running roughly between North Avenue and Division Street, bordered by the lakefront to the east and Halsted Street to the west. It is a walkable, dense neighborhood with a mix of historic greystones, vintage mid-rises, and newer construction. Most of the housing stock is condos and townhomes, with a smaller number of multi-unit buildings and single-family homes. For a veteran buyer using VA financing, that breakdown matters from the very first property search.
Understanding What VA Financing Covers in Old Town
The VA loan benefit is one of the strongest financing tools available to eligible veterans, active-duty service members, and surviving spouses. It typically requires no down payment, has no private mortgage insurance, and generally offers competitive rates. But the VA does impose property eligibility requirements, and those requirements interact with Old Town's market in specific ways.
- Single-family detached homes: These are the most straightforward VA purchase. If a property passes the VA appraisal and meets minimum property requirements, financing generally proceeds without building-level complications.
- Townhomes: VA financing works on townhomes, though if the townhome is part of a condo association or planned unit development, additional review may apply depending on how the association is structured. Your lender will confirm what documentation is needed.
- Condos: This is where veteran buyers in Old Town need to pay close attention. The VA maintains a database of approved condo projects. To use VA financing on a condo, the building must either already appear on that approved list, or the lender must obtain a spot approval — a process that requires the association to meet VA guidelines on owner-occupancy ratios, insurance, delinquency rates, and other factors. Not all Old Town buildings qualify, and not all associations are willing to go through the process.
The practical implication is that your condo search in Old Town should begin with the VA's approved condo project list, not Zillow. You want to know which buildings are already cleared so you are not three weeks into a negotiation on a unit in a building that cannot be approved.
Before Writing an Offer on a Condo
If you find a condo in an approved building — or your lender confirms a spot approval is achievable — there are specific things to ask the listing agent before you write an offer. These are the questions that protect you from surprise costs after you are under contract.
- What is the reserve fund balance? A well-funded reserve means the building can cover major repairs without levying special assessments on owners.
- Are there any upcoming special assessments? These are charges passed to individual owners for major building expenses. You want to know about them before you commit.
- Were there any past special assessments, and what were they for? Past assessments reveal how the building has handled major expenses and whether issues keep recurring.
- Are there any known major issues with the building — roof, elevators, facade, systems?
Everything else — meeting minutes, bylaws, rules, the 22.1 disclosure, and HOA financials — is reviewed after you are under contract during the attorney review period. Do not let anyone tell you that you need all of that before writing an offer.
Getting Your VA Financing in Order First
If you are serious about buying in Old Town with a VA loan, your financing setup needs to happen before you tour a single property. This is how competitive VA buyers operate in a neighborhood where well-priced units move quickly.
- Obtain your Certificate of Eligibility. This is the document that confirms your entitlement to the VA loan benefit. You can request it through the VA, or your lender can often pull it directly. Without it, a lender cannot properly pre-approve you.
- Choose a lender with real VA loan experience. Not every mortgage lender handles VA loans regularly. In a competitive market like Old Town, you need someone who can close on time, communicate clearly with listing agents, and navigate condo approval issues without delay. Ask any lender directly how many VA loans they close per month before you commit.
- Get fully pre-approved, not just pre-qualified. In Old Town, sellers — and especially condo associations with their own review timelines — respond better to buyers who are fully underwritten. A pre-approval letter that has been through income and asset verification carries real weight.
- Understand your VA funding fee. Most VA purchases involve a funding fee, which varies based on your down payment and whether you have used the benefit before. Veterans with a qualifying service-connected disability may be exempt — confirm your status before assuming either way.
- Clarify your entitlement situation. If you have used a VA loan before and still have an outstanding balance, you may have remaining entitlement available. A VA-experienced lender will walk through your entitlement position so you know exactly what you are working with.
Once your financing is organized, the full Chicago Buyer's Roadmap walks through every step of the purchase process from search through closing, which is useful context for any first-time buyer or anyone new to purchasing in Chicago specifically.
How Old Town's Market Affects VA Buyers
Old Town is not a slow, pick-your-spot kind of market. Inventory moves, and the units that are priced well and in good condition tend to attract multiple buyers. That creates a specific challenge for VA buyers: some sellers or listing agents have outdated perceptions about VA loans taking longer or being more complicated to close. That perception is usually the result of working with the wrong lender or the wrong buyer's agent.
When a VA buyer is fully pre-approved, working with a lender who is responsive and experienced, and represented by an agent who can clearly communicate the strength of the offer, VA financing is not a liability. It is just another financing type. The work you do upfront — getting your COE, choosing the right lender, knowing which buildings are approved — is what makes that case easy to make.
For more context on how the VA loan process plays out in a dense Chicago condo market, the guide for VA loan buyers in Gold Coast covers many of the same dynamics in a neighboring neighborhood with a similar inventory profile.
Working with Riley Hextell as a VA Buyer in Old Town
Riley Hextell is a U.S. Navy veteran who has worked extensively with veteran buyers in Chicago's competitive neighborhoods. He was ranked number one at eXp Realty Illinois for total transactions in 2025, ranks in the top 50 among more than 80,000 agents companywide, and earned the 2024 Chicago Association of Realtors Rookie of the Year award. He has more than 141 five-star Google reviews from clients who have been through exactly this process.
Riley's approach with VA buyers in Old Town is practical: identify which buildings are VA-approved before the search begins, connect buyers with VA-experienced lenders early, ask the right pre-offer questions on condos, and communicate clearly with listing agents so that VA financing is never a reason a seller passes on an offer. Choosing the right agent is as important as choosing the right lender — for a deeper look at what to evaluate when hiring a buyer's agent in Chicago, here is how to think through that decision.
You can reach Riley at 815-545-7476, [email protected], or at rileyhextell.com.
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Frequently Asked Questions
Can I use a VA loan to buy a condo in Old Town, Chicago?
Yes, but the condo building — not just the individual unit — must meet VA approval requirements. The VA maintains a list of approved condo projects, and purchases in non-approved buildings require a spot approval that depends on the association meeting specific guidelines. Your lender will confirm whether a building qualifies before you go too far in the process.
How do I find VA-approved condos in Chicago?
The VA maintains an online searchable database of approved condo projects. You can search by state, county, and project name to see which buildings are currently approved. Your VA lender should also be pulling this list as part of helping you search. Working with an agent who knows the local market can further narrow down which approved buildings actually make sense for your needs.
Do I need a down payment to use a VA loan in Old Town?
For most eligible veterans and service members, the VA loan benefit allows a zero down payment purchase. There is still a VA funding fee in most cases, which can be rolled into the loan or paid at closing, and your service-connected disability status affects whether you are exempt from that fee. A VA-experienced lender will walk through your specific situation.
How long does it take to close on a VA loan in Chicago?
VA loan closing timelines are similar to conventional loans when the buyer is fully pre-approved and the lender is experienced with VA products. Delays typically come from choosing an inexperienced lender, waiting too long to start the COE process, or running into condo approval issues. With the right team in place, VA closings in Chicago are not meaningfully slower than any other financing type.