You just got engaged. The champagne is barely gone, the ring still feels new on your finger, and somewhere between venue tours and telling your families, one of you said it: "Maybe we should just buy a place." It is a completely reasonable thought. Old Town is one of the most livable neighborhoods on the North Side — close to the Loop, walkable, full of character — and buying here together can be one of the best financial decisions you make as a couple. But it is also one of the most complicated things two people can do together, especially when you are doing it for the first time and doing it in a competitive Chicago market.
This guide is for couples in Old Town who are ready to move past the idea and figure out the actual steps.
Getting Your Financial Picture Straight — Together
Before you look at a single listing, sit down and put your numbers on the table. Both of them. That means income, credit scores, existing debt, savings, and what each of you actually has liquid for a down payment and closing costs.
In Chicago, closing costs typically run 2 to 3 percent of the purchase price on top of your down payment. For a $550,000 condo in Old Town, that is another $11,000 to $16,500 you need available at closing beyond whatever you put down. Many couples miscalculate this and drain their reserves.
Your credit scores matter enormously. If one of you has a significantly lower score, it can affect your interest rate — and in some cases, it makes sense for only the higher-credit partner to apply for the mortgage. That is a conversation worth having with a lender early. The trade-off is that you may qualify for less if only one income is used. A good loan officer will walk you through both scenarios.
Get pre-approved — not pre-qualified — before you tour a single home. In Old Town, well-priced properties move fast. Sellers will not take your offer seriously without a pre-approval letter from a reputable lender.
What Old Town Actually Costs Right Now
Old Town is not a starter neighborhood in the traditional sense. The location, proximity to Lincoln Park, the lakefront, and easy access to the Brown and Red lines command a price. As of mid-2026, you are generally looking at:
One-bedroom condos: $350,000 to $500,000
Two-bedroom condos: $475,000 to $750,000
Two- and three-bedroom townhomes: $700,000 to over $1.2 million
Single-family homes: rare and priced well above $1 million in most cases
Most couples buying their first home together in Old Town land in a two-bedroom condo or a smaller townhome. The two-bedroom gives you a home office or future flexibility, and Old Town has a solid supply of them in well-maintained vintage buildings and newer construction.
HOA fees in Old Town vary widely. Older greystones that have been converted into condos can have fees under $400 per month. Larger buildings with doormen, gyms, and rooftop decks often run $700 to $1,200 or more. That monthly number matters for your debt-to-income ratio when qualifying for a mortgage, so factor it in early.
If you want to understand how similar budgeting conversations play out in a comparable North Side neighborhood, the first-time buyer's guide to Lakeview covers the cost breakdown in useful detail.
Condo Due Diligence: What to Ask Before You Make an Offer
The majority of first homes purchased in Old Town are condos, and condos require a different kind of scrutiny than single-family homes. Before you write an offer on any condo building, ask the listing agent four things:
What is the reserve fund balance — is the building adequately funded?
Are there any upcoming special assessments?
Have there been any past special assessments?
Are there any known major issues with the building?
That is your pre-offer homework. A building with a thin reserve fund or a looming special assessment for a new roof or tuckpointing is a financial risk that changes the math on what you should offer.
Everything else — the building's meeting minutes, bylaws, rules and regulations, the 22.1 disclosure from the condo association, and HOA financial statements — is reviewed after you go under contract, during the attorney review period. That is when your real estate attorney earns their fee. Do not let anyone tell you that you need all of that before writing an offer. You do not.
Title: How You Hold Ownership Together Matters
One of the most overlooked decisions for unmarried or newly married couples buying together is how to take title. In Illinois, the two most common options are joint tenancy with right of survivorship and tenancy in common.
Joint tenancy means that if one of you dies, the other automatically inherits the full property — no probate required. Tenancy in common allows each partner to own a defined percentage and pass their share to whoever they designate in a will.
If you are not yet married when you close, this decision carries real weight. Talk to a real estate attorney about which structure fits your situation. Riley can refer you to attorneys who handle this regularly for couples in exactly your position.
How the Home Search Actually Goes in Old Town
Old Town is a compact neighborhood. You are not choosing between twenty micro-markets — you are choosing between streets, building types, and floor plans. A vintage two-flat conversion on Eugenie Street feels different from a new construction mid-rise on Wells. Both can be great. Knowing what matters most to you before you start touring saves everyone time.
Make a list — separately first, then together — of your actual priorities. Parking matters here because street parking is difficult. Outdoor space matters because Old Town has it in some buildings and not others. Proximity to the train, proximity to the park, in-unit laundry versus shared — write it down so you are not reinventing the conversation every time you walk into a showing.
When you find something you both like, be ready to move. Old Town's inventory can be tight, and the most fairly priced properties in good buildings attract multiple offers. Your pre-approval, a clear sense of your number, and a strong agent are what position you to win without overpaying.
Working with the Right Agent
Buying your first home together is not the time to work with a friend's cousin who does real estate on the side. Old Town has enough nuance in its building stock, its condo associations, and its pricing that you want someone who knows the neighborhood and has done this at volume.
Riley Hextell is the number one agent at eXp Realty Illinois for total transactions in 2025, ranked in the top 50 of more than 80,000 agents companywide, and won the 2024 Chicago Association of Realtors Rookie of the Year award. He has guided couples through exactly this process — including the hard conversations about budget, title, and what to do when you both want different things. If you want to understand what separates agents who do this well from agents who do not, what makes a top Chicago real estate agent is worth reading before you decide who to work with.
Riley works with buyers throughout Old Town and across the North Side. He is a US Navy veteran and brings a straightforward, no-pressure approach to the process. You can reach him at 815-545-7476, [email protected], or rileyhextell.com.
One More Thing: Buying Together Is a Financial Partnership
Getting engaged is exciting. Buying a home is serious. The two happening at the same time means you are making a major financial commitment to each other before the wedding, and you should go into it with your eyes open.
Talk about what happens if the wedding is delayed. Talk about who pays what portion of the mortgage if one of you loses income. Talk about what you would do if you needed to sell in three years instead of seven. These conversations are not pessimistic — they are the same conversations that protect the partnership you are building.
Old Town is a great place to start that life. The neighborhood rewards people who are there for the long term, and most couples who buy here feel that within the first year.
Couples who are weighing Old Town alongside nearby options sometimes find it useful to look at how engaged couples are approaching the same process in Lakeview, which covers overlapping questions about budget, title, and shared decision-making in a similarly competitive North Side market.
Frequently Asked Questions
FAQ: Can we buy a home in Old Town before we are officially married?
Yes. Illinois has no requirement that buyers be married. You will want to discuss how to hold title — joint tenancy or tenancy in common — with your real estate attorney before closing, since that decision has legal and financial implications that vary depending on your situation.
FAQ: How much do we need saved before buying a condo in Old Town?
For a $550,000 condo with a 10 percent down payment, you are looking at $55,000 down plus roughly $11,000 to $16,500 in closing costs — so somewhere around $66,000 to $72,000 before moving expenses or any immediate repairs. Some loan programs allow as little as 3 to 5 percent down, but at Old Town price points, conventional financing with at least 10 percent down is common.
FAQ: What should we ask about a condo building before making an offer?
Before writing an offer, ask the listing agent about the reserve fund balance, whether there are any upcoming special assessments, whether there have been any past special assessments, and whether there are any known major building issues. Everything else — meeting minutes, bylaws, the 22.1 disclosure, and financial statements — is reviewed during the attorney review period after you go under contract.
FAQ: How competitive is the Old Town market for buyers?
Old Town is consistently one of the more competitive neighborhoods on Chicago's North Side. Well-priced two-bedrooms in good buildings tend to attract multiple offers, especially in spring and early summer. Being pre-approved, knowing your budget, and working with an experienced agent who can move quickly are all factors that meaningfully improve your outcome.