Chicago home sellers could ask more. Agents say don’t.

By Dennis Rodkin, Crains Chicago Business, March 17, 2026 05:50 AM CDT

When putting a home on the market, the temptation to put an ambitious price tag on it is always strong, and recent data show Chicago-area sellers can afford to push it up a little.

Even so, many real estate agents are cautioning their clients not to stretch the asking price.

A key reason is that they worry sellers with an aggressive ask can risk upending the prevailing mode of selling homes, where multiple offers put the sellers in a power position where they can dictate other terms of the deal, such as the closing date.

As the spring homebuying season warms up, sellers may want to consider which route they prefer.

Home prices have been rising steadily in the Chicago metro area, but sellers’ asking prices aren’t keeping up, the latest data from online real estate marketplace Redfin show.

In the month ended March 8, the median price of homes sold in the Chicago metro area was up 5.5% from a year earlier. Meanwhile, the median price asked by sellers was up by a little less than half that, 2.71%.

The space in between those two figures suggests sellers could push their prices higher to capture the total price that’s waiting for them in the market.

“It doesn’t take a chief economist to see that the market can stand higher asking prices,” said Phil Skowron, a Compass agent. “Inventory is very low, and there is a lot of demand out there. The answer is people can ask a little more.”

One reason asking prices aren’t keeping up may be Midwesterners’ habitual conservatism, both Skowron and Jim Kinney of Baird & Warner said.

“What you’re seeing is trepidation from people about raising prices too much,” Kinney said. Sellers “aren’t realizing how much of an up market we’re in.”

Chicago-area home price growth has been leading the nation for much of the past year. Another sign of the up market that a big share of listed homes go under contract to buyers in less than two weeks.

Sellers in the northern suburbs may be more hip to the market’s strength. Their asking prices aren’t only keeping up with selling prices, they’re running ahead. In the Lake County, Illinois, metro area, the second metro area in the Chicago region, the median sale price is up 7%, according to Redfin’s data, and asking prices are a little above that, up 7.29%.

The data from Redfin is metro-wide, and as such doesn’t account for the fine points of sub-markets. In the Chicago metro that would include the upper-end condo market downtown, where prices have been slow to recover from the pummeling they took in the early 2020s. One among many examples is the high-floor Park Tower condo that came on the market three and a half years ago at $13.5 million but now is down to asking $5.9 million.

In the nation’s other major metros, the data show a mix of optimistic pricing and caution.

The biggest optimism gaps are in Phoenix, where the median sale price is down 2%, but sellers are asking nearly 2% more than they were a year ago, and Dallas, with roughly the same gap as measured in percentage points. Sale prices there are down 5%, but asking prices are up 0.62%.

The largest caution gap by far, more than six percentage points, is in Philadelphia. Sale prices are up 8% from a year ago, but sellers are asking only 1.72% more than they were then.

Here’s why agents are counseling their clients not to fill the gap: in much of the Chicago-area market, it’s become the norm to set the asking price where it will attract lots of attention from potential buyers and multiple bids.

Birthed by years of low inventory, the notion of scarcity has morphed into a selling strategy. The aim is to “compress the time on the market by creating a sense of urgency,” said Jennifer Ames of Engel & Volkers.

Because buyers, as well as their agents, are zeroed in on what homes in their target zone are worth, “the risk is that if somebody asks more, the buyers will not show up or they’ll dribble in instead of rushing in,” Ames said.

Price it below where it’s likely to sell and they’ll come, both Ames and Jeff Lowe of Compass said.

Like a nightclub with a red velvet rope out front, a home with a low price makes everybody eager to get inside. And crowds “give the seller leverage,” Lowe said.

“If you swing for the fences” with an overly ambitious asking price,” Lowe said, “you might strike out.” Better to hit a single or a double and let buyers bid it up the rest of the way, he said.

Bidding will very likely push the sale price up above the asking price, but on top of that, “you have leverage on all your terms,” Lowe said.

When in competition to land their dream house, buyers may be more willing to accept the sellers’ preferred closing date, to ask for credits based on deficiencies found during the property inspection, or in other ways keep the seller from getting annoyed and moving to the next-best offer.

Kim Kerbis of @properties Christie’s International Real Estate is another proponent of what she calls strategic under-pricing. She suggests that in one sense it’s good for the buyer as well as the seller.

All home sales are about what the market will pay for a property, and under-pricing, Kerbis said, helps reinforce prices.

When a buyer learns the property is so sought-after that the sellers’ agent has a dozen or more showings scheduled in the first few days, she said, “they feel better about the price and about stretching up from there.”

Skowron concurs. “When buyers see that a lot of people want something,” he said, “they step up.”

That too is a mark of financial conservatism. “Nobody wants to be the one who went all out and paid way too much,” Kinney said. “We don’t do that in the Midwest.”