What Chicago Home Sellers Actually Ask Me

Updated June 2026

I’ve spent more than two decades selling condos and homes in downtown Chicago, and the same questions come up on almost every listing. Here’s what I tell my sellers, in plain language, before we ever get to the closing table.

What does it cost to sell a home in Chicago?

Most sellers are surprised that the sale price isn’t what lands in their account. Plan on roughly 7% to 10% of the sale price in total costs. That covers the real estate commission, title and closing fees, your attorney, the city and county transfer taxes, and your property tax proration credit to the buyer. If you still have a mortgage, your payoff comes out of the proceeds too.

I give every seller an estimate up front so there are no surprises. The title company prepares the actual figures, and your attorney reviews them with you about a week before closing, so you’ll know your real numbers well before closing day, not at the table.

Who pays the Chicago transfer tax, and how much is it?

This is the one almost everyone gets wrong. The combined transfer tax in Chicago is $10.50 per $1,000 of the sale price, plus small state and county amounts, and it’s split between buyer and seller.

The buyer pays $7.50 per $1,000, which is the City of Chicago’s portion. The seller pays $4.00 per $1,000 total: $3.00 to the city, plus $0.50 to Cook County and $0.50 to the state.

So on a $500,000 sale, the buyer’s transfer tax is $3,750 and the seller’s is $2,000. These amounts appear on your settlement statement, which you’ll review with your attorney before closing.

Do I still have to pay the buyer’s broker commission after the NAR settlement?

This is the most misunderstood change in real estate right now. A lot of sellers think the settlement means they no longer pay the buyer’s side. That’s not what changed.

First, a point that trips people up: the commission is paid to the buyer’s brokerage, not to the agent directly. The buyer signs a written agreement with the brokerage, with their agent named in it, and that agreement sets the commission the buyer negotiated, commonly 2.5% to 3%. The brokerage is paid at closing and then pays the individual agent according to their own split. An agent is never compensated directly. The same is true on my side as the listing agent, my brokerage is paid, then I’m paid from that.

When the buyer’s agent writes the offer, the contract includes a field for the buyer’s broker compensation that has to be completed. So the compensation is part of the deal from the very first offer.

What the settlement changed is how that compensation is marketed, not whether it exists. Before, the listing side could publish the buyer’s broker commission right on the MLS and advertise extras like a bonus. That’s no longer allowed. Compensation is now negotiated deal by deal and written into the offer instead of broadcast on the listing.

Here’s the part sellers miss: the commission comes out of the transaction no matter who is named as paying it. If you decline to cover the buyer’s broker, the buyer still owes that commission under the agreement they signed, so they pay it themselves, out of pocket, on top of their down payment and closing costs. A buyer draining cash to cover it will simply offer less to make up the difference. And when you cover it, the buyer can fold that commission into their mortgage instead of paying cash, which keeps their offer stronger.

So the real question isn’t whether the commission gets paid. It’s whether it comes off your sale price through a lower offer, or gets handled as seller-paid compensation the buyer can finance. I walk every seller through that math on their specific deal so the decision is based on the actual numbers, not on a headline about a lawsuit.

How do property tax prorations work at closing?

Cook County bills property taxes a year behind. Because the county is always collecting last year’s taxes, you’ll give the buyer a credit at closing for the time you owned the home but haven’t been billed for yet.

Here’s the part most sellers don’t know: the credit is calculated as a percentage of the most recent tax bill, and that percentage is negotiated in the contract. It’s typically somewhere between 100% and 110%, sometimes as high as 115%, with a cushion built in because Chicago taxes tend to rise. The higher the percentage, the bigger the credit you give the buyer, so it comes straight out of your proceeds.

This is one of the most overlooked negotiation points in a Chicago sale, and it’s not locked in stone when you sign. If your attorney doesn’t agree with the proration rate, they can renegotiate it during the attorney review period. On a home with a $10,000 tax bill, the difference between 100% and 110% is about $1,000 of your money, so it’s worth getting right. I walk every seller through their specific proration so they see exactly where the number comes from.

Why do I need a real estate attorney to sell in Chicago?

In Cook County, both the seller and the buyer hire their own attorney. It’s not optional the way it is in some states. Your attorney reviews and modifies the contract during the attorney review period, drafts the deed, handles the title work, clears any city items, reviews your closing figures with you ahead of time, and represents you at closing.

Most real estate attorneys charge a flat fee for the entire transaction, and the average is around $950. It’s one of the best values in the whole deal. A good attorney is one of the most important people on your team, and I work with mine on every deal so nothing falls through the cracks.

What is the attorney review and inspection period?

Once you and the buyer both sign, there’s a five-business-day window. During that time the buyer does their inspection, and both attorneys can approve the contract, propose changes, or renegotiate terms based on what turns up. The deal isn’t fully firm until that period closes.

This is where a lot of transactions wobble, and it’s the part I track most closely. Knowing exactly where you are in that window, and what’s still outstanding, is half of keeping a deal together.

Do I have to be there for showings or closing?

For showings, it’s usually better if you’re not there. Buyers explore more freely and ask more honest questions when the owner isn’t in the room, and your agent manages the whole process. I handle showings so you don’t have to be home for them.

Closing is the same story. In most Chicago sales, the seller signs the closing documents in advance, prepared by their attorney, and the attorney attends the closing on the seller’s behalf. You don’t have to be present on the closing date itself. This surprises a lot of sellers, especially anyone who’s moved out of state or is juggling a busy schedule. I make sure my sellers know well ahead of time exactly what they need to sign and when, so closing day is a non-event.

What’s the difference between the two contracts used in Chicago?

You’ll likely sign one of two standard forms, and they’re both binding, widely used contracts.

The first is the Multi-Board Residential Real Estate Contract, currently version 8.0. It’s the longer, more detailed form, approved by a wide group of REALTOR and bar associations across Illinois. It spells out financing contingencies, inspection options, condo association requirements, and deadlines in precise language. Many attorneys prefer it because the timelines and contingencies are clearly defined, which leaves less room for disputes later. It’s the contract I use with my buyers.

The second is the Chicago Association of REALTORS Condominium contract, a shorter form written specifically for condo sales. It covers the condo essentials, parking and storage, association document delivery, and the same five-business-day attorney review, in a more streamlined format.

Both get you to the same place. I lean toward the 8.0 because the added structure protects everyone and keeps the timeline crystal clear, and my attorney prefers it too.

What documents do I have to provide if I’m selling a condo?

If you’re selling a condo, Illinois law requires you to give the buyer a disclosure package under Section 22.1 of the Condominium Property Act. That includes the association’s budget, declaration and bylaws, a summary of insurance, and recent board meeting minutes.

Buyers and their lenders read these closely. If your building has low reserves or a special assessment coming, expect questions, and sometimes a request that you pay the assessment at closing. I help my sellers get this package together early so it doesn’t slow the deal down.

Can I sell my condo if I have a tenant in it?

Yes, but it takes more planning than a vacant unit, and the building’s rules matter as much as the lease.

Start with the lease. If your tenant is on a lease, it transfers with the sale, the new owner takes the unit subject to that lease. For an investor buyer that can be fine. But here’s what most people miss: many downtown buildings have rental caps, and some have a waitlist to rent. So even an investor who’s happy to inherit your tenant may find that once the lease expires, they can’t re-rent the unit without going on the building’s waitlist. That makes a tenant-occupied unit in a rental-capped building far less attractive to investors than it looks on paper. And most owner-occupant buyers don’t want to inherit a tenant they have to wait out before they can move in. So depending on your building’s rules, the smart move is often to time the closing for after the tenant moves out, so you’re delivering a vacant unit.

The Chicago Residential Landlord and Tenant Ordinance lets you show the unit with the tenant in place during the 60 days before the lease ends. So if your building isn’t investor-friendly, you can use that window to market the unit while timing the closing to the tenant’s move-out.

There’s also the question of how your tenant keeps the place. You can ask a tenant to clean up or have the unit staged, but you don’t fully control how it shows day to day. If the tenant is messy or the unit is poorly furnished, it won’t photograph or show well, and that costs you. On the other hand, a clean tenant in a well-kept, nicely furnished unit can actually show better than an empty condo. It’s genuinely case by case, and it’s one of the first things I’d talk through with you before we set a listing timeline.

How do I find out if my building has assessments that could affect my sale?

Order a paid assessment letter (sometimes called a status letter) from your condo association early. It confirms you’re current on dues and discloses any outstanding balance or upcoming special assessment. Buyers and their lenders will ask about it, along with the building’s reserves and financial health, so it’s better to have it in hand before questions come up. These letters can take time and there’s often a fee, so I get them ordered early in the process. A delay here is one of the avoidable ways a closing slips, and I’d rather it never come up.

When is the best time to list in Chicago?

The Chicago market is seasonal. Buyer activity picks up from late winter into early summer, with a second, shorter wave right after Labor Day. The deep winter months tend to be slower, with fewer buyers and longer days on market.

That said, the best time depends on your building, your price point, and your competition right now. I’d rather look at what’s actually happening in your neighborhood than give you a calendar rule.

How long does the closing process take?

Once you accept an offer, plan on about 30 to 45 days to close. That window covers attorney review, the inspection, the appraisal, and the buyer’s mortgage underwriting. Cash deals can move faster. I keep every party on schedule so we hit the closing date we agreed to.

Should I sell my New Eastside or Lakeshore East condo off-market or as a private listing?

No, and the evidence is one-sided. When sellers skip the MLS, they consistently leave money behind. Zillow's analysis of 10 million transactions put the total at more than $1 billion lost over two years, around $5,000 for a typical seller and as much as $30,000 in some markets. The academic numbers are even starker: a Bright MLS and Drexel University study of over a million sales found on-MLS homes sold for 17.5% more, roughly $54,000 extra for the average seller. Private listings also dragged on far longer before selling, and nearly 90% landed on the MLS eventually anyway. Every home I list goes on the MLS through MRED, in front of the whole buyer pool, because the only party a private listing reliably serves is the brokerage holding it.  I answer this and other seller questions on my FAQ page.