The ring is on your finger and the congratulations are still coming in. Somewhere between the celebration dinners and the venue tours, a different kind of conversation starts: what do we actually want our life to look like, and where do we want to live? For a lot of Chicago couples, that question leads straight to Lakeview. It is one of the most livable neighborhoods on the North Side — walkable, well-connected, with a range of housing stock that can realistically accommodate a first-time buyer couple on a combined income. But buying a home together for the first time, especially right around an engagement or marriage, comes with layers that a solo purchase does not. This guide walks you through what that process actually looks like in Lakeview and the broader Chicago market, step by step.
Why Lakeview Makes Sense for Newly Coupled Buyers
Lakeview sits between Wrigleyville to the south and Roscoe Village and Lincoln Square to the north, with Boystown and East Lakeview forming the lakefront edge. The neighborhood offers condos, vintage two-flats, townhomes, and single-family houses — which means couples at different price points and with different priorities can usually find something that fits. Transit access is strong, with the Red, Brown, and Purple lines running through the area. Walkability scores are high across most of Lakeview. For couples who are combining incomes for the first time, this neighborhood represents a genuine on-ramp to Chicago homeownership without requiring a move far from the city center.
Step One: Get Honest About the Numbers Before You Tour Anything
The most common mistake engaged couples make is falling in love with a home before they understand what they can actually afford together. Before you schedule a single showing, sit down and work through your combined financial picture with specificity.
Start with your gross monthly income as a couple. Lenders typically want your total housing costs — principal, interest, taxes, insurance, and any HOA dues — to stay at or below 28 to 31 percent of your gross monthly income, though some programs allow higher ratios. On a combined income of $180,000, that generally puts your comfortable price range somewhere in the $550,000 to $700,000 range depending on your down payment and credit scores. That is a meaningful part of the Lakeview market.
Pull both of your credit reports before talking to a lender. If one partner has a lower score, that score will anchor your mortgage terms. In some cases it makes financial sense to apply for the mortgage in only one partner's name if that person has significantly better credit — but this has trade-offs, particularly if only one person is on title. Talk through the implications with a lender and a real estate attorney before deciding.
Also account for one-time costs that often get underestimated: closing costs in Illinois typically run 2 to 3 percent of the purchase price on top of your down payment, there is a Chicago transfer tax, and moving costs are real. Couples planning a wedding at the same time need to budget both events simultaneously rather than treating them as separate financial universes.
Step Two: Decide What You Are Actually Buying — and Why
Lakeview offers two very different first-home paths for couples. One is the condo route, which tends to be lower maintenance, often comes with amenities, and is more liquid if your plans change. The other is the multi-unit or single-family route, which requires more capital but offers more control over your space and, in the case of a two-flat, potential rental income.
The right choice depends on answers to questions most couples haven't asked each other yet. Are you planning to start a family in the next two or three years? How important is outdoor space? Do either of you work from home in a way that requires a dedicated room? Is one partner more comfortable with the responsibilities of a larger building? Do you expect to stay five or more years, or does career flexibility matter more than roots right now? These are not abstract lifestyle questions — they directly affect what type of property to prioritize and what trade-offs to accept.
For couples who are genuinely uncertain about timeline, a condo in a well-maintained Lakeview building is often the more flexible starting point. For those who are confident they are putting down roots, a vintage two-flat or a single-family house in Roscoe Village or the western parts of Lakeview gives more room to grow.
Step Three: Find the Right Agent Before You Start Looking
This step is worth laboring on because the right agent in a neighborhood like Lakeview will save you money, protect you from bad purchases, and make the process significantly less stressful. You want someone who knows the hyper-local inventory, understands Chicago-specific contract language, and has enough transaction volume to handle complications without panicking.
When evaluating agents, look at how many transactions they have actually closed — not just what their bio says. If you want a detailed breakdown of what separates effective Chicago agents from average ones, this breakdown of what to look for in a Chicago REALTOR is worth reading before you start interviewing anyone.
Riley Hextell is a Chicago agent based at eXp Realty, ranked number one in Illinois at eXp for total transactions in 2025 and in the top 50 of more than 80,000 agents companywide. He was named the 2024 Chicago Association of Realtors Rookie of the Year, and has more than 135 five-star Google reviews from clients across the city. Riley works closely with couples navigating their first purchase together and understands the particular pressures that come with buying during an engagement or early marriage. Reach him at 815-545-7476, [email protected], or rileyhextell.com.
Step Four: Get Pre-Approved — Not Just Pre-Qualified
Pre-qualification is a quick calculation based on what you tell a lender about your finances. Pre-approval means the lender has pulled your credit, verified your income and assets, and issued a conditional commitment. In Lakeview's market, sellers and listing agents take pre-approval seriously and may not consider offers from buyers who only have a pre-qualification letter.
Use a lender who closes loans on time and communicates well. A seller with multiple offers will sometimes favor a buyer with a local lender over an online bank — not because it affects the terms, but because listing agents know from experience which lenders can actually execute. Ask your agent for lender recommendations, and interview two or three before committing.
Step Five: Understanding Lakeview's Condo Market Specifically
A significant portion of Lakeview home purchases are condos, and condos require a layer of diligence that single-family purchases do not. Before you write an offer on a condo, ask the listing agent four things: What is the reserve fund balance, and is the building well funded? Are there any upcoming special assessments? Have there been past special assessments, and what were they for? Are there any known major issues with the building?
Those four questions will tell you whether the building is financially healthy enough to pursue. If the reserve fund is thin and there is a big-ticket item on the horizon — a new roof, tuckpointing, elevator work — that could translate into a special assessment that costs you thousands out of pocket after closing.
Everything else — the meeting minutes, bylaws, rules and regulations, the 22.1 disclosure from the condo association — is reviewed after you go under contract, during the attorney review period. That is the appropriate time to dig into those documents with your real estate attorney.
Lakeview has a mix of well-run and poorly-run condo associations. Vintage buildings from the 1920s and 1930s can be beautifully maintained or quietly deferred — the financials will tell you which. Newer construction typically has cleaner documentation but may carry higher HOA dues.
Step Six: Making an Offer as a Couple
Illinois is an attorney review state, which means every residential real estate contract includes a five-business-day attorney review period during which either party can modify or cancel the contract without penalty. This is a meaningful protection for first-time buyers, and you should absolutely hire a real estate attorney — your own, not one recommended by the other party.
When you make an offer as a couple, you need to decide how you will hold title. Joint tenancy means each partner owns an equal share with right of survivorship. Tenancy in common allows for unequal ownership percentages, which can matter if one partner is contributing significantly more to the down payment. Your attorney will walk you through the implications; just know the question is coming and think about it in advance.
Offer strategy in Lakeview varies by submarket. In well-priced condo listings in East Lakeview and near the Red Line, multiple offer situations are not rare. In larger buildings or on properties that need work, there is often more room to negotiate. Your agent should give you a specific comp analysis — not a general neighborhood overview, but a breakdown of similar sales in the last 90 days on comparable properties — before you decide on a number.
Step Seven: The Closing Process and What to Expect
From accepted offer to closing in Illinois typically takes 30 to 45 days for a standard purchase with financing, though timelines vary. During that window you will have your home inspection, your attorney review period, your appraisal, and your final loan underwriting. Each of these can surface issues that require negotiation or decisions.
The inspection is a full review of the property's systems and condition. Inspectors are not pass-fail arbiters — they document what they find and you decide how to respond. For a condo, the inspection covers the unit itself; common elements like the roof and boiler are the association's responsibility. For a single-family or multi-unit, the scope is much broader.
Budget for the unexpected. Even well-maintained properties have items that come up in inspection. Know your limits in advance: what is a deal-breaker, what is worth negotiating a credit for, and what you are willing to take on as a project.
After attorney review is resolved and inspection is complete, your lender will order the appraisal. If the property appraises below the purchase price, you will need to negotiate with the seller, make up the difference in cash, or walk away. In a competitive market, some buyers include an appraisal gap clause in their offer to address this scenario upfront.
The final walk-through happens within 24 hours of closing. Review the property's condition and confirm that any agreed-upon repairs were completed. Closing itself is typically held at a title company, and you will need to wire your down payment and closing costs in advance.
Building a Life in Lakeview
Buying your first home as a couple is one of the more meaningful financial decisions you will make together — not because of the dollar figure, but because of what it requires: honest conversations about money, aligned priorities, and a shared commitment to a place. Lakeview is a neighborhood that rewards that investment with walkable streets, an active community, and housing that tends to hold value over time.
The couples who navigate this process best are the ones who slow down before they start looking — who get their finances in order, ask hard questions of each other and of their agent, and treat the purchase as a financial decision first and an emotional one second. The emotions are not wrong; they are part of it. But the structure protects you.
If you are newly engaged or recently married and thinking about making Lakeview your first home together, Riley Hextell works with couples exactly like you. His track record in Chicago's competitive market speaks for itself, and if you want to understand what drives results for buyers in this city, his journey to Rookie of the Year gives you a clear picture of how he approaches his work.
Frequently Asked Questions
Should both partners be on the mortgage when buying a home together in Chicago?
Not necessarily. If one partner has significantly stronger credit, applying for the mortgage in that person's name alone can result in better loan terms. The trade-off is that the non-borrowing partner's income cannot be used to qualify. Both partners can still be on the title even if only one is on the loan. This is a nuanced decision — discuss it with your lender and your real estate attorney before applying.
How much do we need saved before buying a condo in Lakeview?
For a conventional loan with 10 percent down on a $500,000 condo, you would need $50,000 for the down payment plus roughly $10,000 to $15,000 for closing costs, which include the Chicago and Illinois transfer taxes, title insurance, and lender fees. Some loan programs allow as little as 3 to 5 percent down, but in a competitive market a higher down payment often strengthens your offer. Factor in moving costs and a reserve for post-move expenses.
Is Lakeview a good neighborhood to buy in if we are not sure how long we will stay?
Lakeview condos tend to be relatively liquid compared to some other Chicago neighborhoods because demand from renters and buyers is consistently strong. If you buy at or below market value in a well-run building and stay at least three to five years, you are likely to recoup your transaction costs and potentially see appreciation. If your timeline is genuinely two years or less, renting may be more financially sound. Your agent can help you model the rent-versus-buy math with current Lakeview data.
What makes buying a home during an engagement different from buying as a married couple?
Legally, unmarried partners buying together in Illinois should be especially deliberate about how they hold title and how they document any unequal financial contributions. A real estate attorney can draft an agreement that protects both parties in the event the relationship changes before closing or shortly after. Married couples purchasing in Illinois are generally afforded more automatic legal protections, but documentation of individual contributions to the down payment is still worth formalizing.