Key takeaways:
- Get pre-approved before you tour a single property — Old Town moves fast, and sellers won't wait for financing conversations to start.
- Decide early how you'll hold title together, because that decision has real legal and financial consequences worth reviewing with an attorney.
- Old Town is predominantly a condo and townhome market, so budget for monthly assessments and ask the right questions about building health before writing an offer.
- Aligning on must-haves versus nice-to-haves before you start touring saves arguments and helps your agent find the right properties faster.
Newly engaged and married couples buying their first home together in Old Town should do four things before scheduling a single showing: get pre-approved as a couple, decide how you'll hold title, agree on a realistic budget that accounts for assessments and closing costs, and have an honest conversation about what each of you actually needs in a home versus what sounds appealing. Old Town is a high-demand, low-inventory neighborhood where well-priced properties attract multiple offers quickly, so couples who have done this work in advance are the ones who actually close.
Old Town sits just north of the Gold Coast, hugging the lakefront and spilling west toward Wells Street, and it draws couples for good reasons: walkable blocks, a genuine neighborhood feel, proximity to the Loop, and a variety of housing types that range from vintage coach houses to modern condo buildings. But those same qualities mean competition is real. Here is how to approach it as a team.
Getting Your Finances in Order as a Couple
This is where most couples stumble, not because they lack the money but because they haven't had the full conversation yet. Engagement and marriage are emotional milestones; a mortgage is a business transaction between two people and a lender. The sooner you separate those things, the smoother the process gets.
A lender will look at both of your credit scores, both of your debt-to-income ratios, and how those numbers interact. If one partner has a significantly lower credit score, the lender may use the lower of the two middle scores to qualify you, which can affect your rate. You don't have to put both names on the loan — some couples choose to have only one borrower qualify, especially when one partner has stronger credit or income — but that's a conversation to have with a mortgage professional before you assume anything.
Here's what to get in front of before your first lender meeting:
- Pull both of your credit reports and review them together. Dispute any errors before you apply.
- Calculate your combined monthly debt obligations — student loans, car payments, existing credit cards.
- Agree on a monthly payment you're genuinely comfortable carrying, not just one a lender will approve.
- Discuss how much of your savings you want to use for a down payment versus keeping in reserve.
- Account for closing costs, which in Illinois typically run in addition to your down payment and include transfer taxes, title fees, lender fees, and prepaid items. Your lender will give you a Loan Estimate that details these — review it carefully.
Once you have that pre-approval letter in hand, you're a real buyer in Old Town's market. Without it, you're just browsing.
Understanding What You're Actually Buying in Old Town
Old Town's housing stock is dominated by condos, with a meaningful supply of vintage three-flats that have been converted to condos, newer mid-rise buildings, and a smaller number of townhomes and single-family homes. Each type carries a different cost profile and lifestyle implication, and couples often disagree about which one they want until they've toured a few.
- Condo (vintage building): Typically lower purchase price, potentially higher deferred maintenance risk; ask about reserve fund and any past or upcoming special assessments
- Condo (newer building): Often higher assessments, more amenities; newer common elements mean less near-term maintenance risk
- Townhome: More privacy, sometimes a garage; assessments usually lower, but check what they cover
- Single-family home: Rare in Old Town; typically commands a premium; no association, but all maintenance falls on you
For any condo, before your agent writes an offer, ask the listing agent these specific questions: What is the reserve fund balance? Are there any upcoming special assessments? Have there been any past special assessments? Are there any known issues with the building? The answers to those four questions tell you a great deal about building health. Everything else — the meeting minutes, the bylaws, the 22.1 disclosure, the HOA financials — is reviewed after you go under contract during the attorney review period. Your attorney will walk you through all of it.
Holding Title: A Decision Worth Taking Seriously
How you hold title to a property together is a legal decision, and it's one many first-time buyers don't think about until they're at the closing table. In Illinois, the common forms for couples are joint tenancy and tenancy in common, and they have meaningfully different implications for what happens to the property if one of you passes away, if you later separate, or if you want to sell your share.
This isn't a decision to make based on what sounds right. Talk to a real estate attorney before closing. Riley often connects buyers with experienced closing attorneys who can explain the options in plain language so couples can choose what actually fits their situation. The goal is for both of you to understand what you're signing.
Aligning on What You Want Before You Start Touring
Couples who skip this step spend a lot of time disagreeing in front of listing agents. The conversation is simple but important: each of you writes down your non-negotiables and your nice-to-haves separately, then compare the lists.
Common points of tension for couples buying in Old Town:
- Space versus location. One partner wants a larger unit and is willing to be one block farther from the Brown Line. The other wants to walk to the Sedgwick stop.
- Outdoor space. A private deck or balcony versus a shared rooftop. Or no outdoor space at all in exchange for a more central location.
- Parking. Old Town has permit parking on many streets, and many buildings don't include a deeded space. Is parking a must-have or something you'll figure out?
- Building type. One partner loves the character of a vintage building; the other is drawn to a newer building with a gym and package room.
- Number of bedrooms. Will one bedroom serve as a home office? Are you planning for a family in the near term?
There are no right answers, but there are answers you need before you tour. Your agent's job is to find properties that actually match your priorities — but only if they know what those priorities are.
The Offer and Negotiation Stage
Old Town is competitive at most price points, and newly engaged or married couples sometimes feel pressure to move faster than they should. The right approach is to move quickly when a property genuinely fits your criteria, and to hold firm when it doesn't — even when it's a beautiful unit.
A well-represented couple in Old Town will typically:
- Review comparable sales with their agent before deciding on an offer price.
- Discuss contingencies — inspection, financing, attorney review — and understand what each one protects.
- Write a clean, well-structured offer that takes both the price and the terms seriously.
- Be prepared for counteroffers and know in advance how far you're willing to go.
- Use the attorney review period to examine the condo documents thoroughly with their attorney.
- Complete a home inspection, even on a condo — the inspector can flag issues inside the unit even when common elements are the association's responsibility.
For buyers navigating Chicago's process for the first time, the full Chicago Buyer's Roadmap walks through every step so you're not learning the sequence as you go.
Working With the Right Agent
Buying together as a couple means your agent is effectively managing two clients with potentially different priorities, timelines, and stress responses. That's actually a skill — and not every agent approaches it well. The best agents find ways to facilitate the honest conversation between partners rather than pushing toward a close.
Riley Hextell has helped dozens of first-time buyers navigate exactly this kind of purchase, and knowing what to look for in a Chicago REALTOR® before you commit to an agent is worth five minutes of your time. Ranked number one at eXp Realty Illinois for total transactions in 2025 and among the top 50 of more than 80,000 agents companywide, Riley brings the volume and the experience to move efficiently in a market like Old Town without cutting corners on the parts that protect you.
To start a conversation, reach out directly: 815-545-7476 | [email protected] | rileyhextell.com.
Frequently Asked Questions
Can we get a mortgage together if we're engaged but not yet married?
Yes. Lenders evaluate joint applications from unmarried couples all the time. Both applicants' credit, income, and debt are reviewed. Some couples choose to have only one partner on the loan if the other's credit profile would weaken the application — your mortgage professional can run both scenarios and show you the difference before you commit.
What is attorney review and why does it matter when buying a condo in Illinois?
In Illinois, most purchase contracts include an attorney review period that begins after the offer is accepted. During this window, your attorney reviews the contract and — for condos — receives and reviews the association's governing documents, financials, the 22.1 disclosure, meeting minutes, and other materials. If anything is a concern, your attorney can raise it during this period. Using an attorney for this step is standard practice in Illinois and strongly recommended.
How much should we budget for monthly costs beyond the mortgage in Old Town?
For a condo in Old Town, your monthly carrying costs will include your mortgage payment, your monthly assessment, property taxes (prorated into an escrow payment by most lenders), and homeowners insurance. Assessments in Old Town vary considerably depending on building age, amenities, and size — your agent will pull the specific assessment for each unit you're seriously considering so you can compare total monthly costs accurately.
Do we need separate real estate attorneys, or can we share one?
In a standard purchase transaction, you and your partner are on the same side of the deal, so sharing one attorney is common and generally appropriate. Your attorney represents the buyer, which is both of you. If you have genuinely conflicting interests — for example, if you're structuring an unusual ownership arrangement — it may be worth consulting separately. Your attorney can advise you if that situation comes up during review.