If a job is bringing you to Chicago, start the neighborhood search 60 to 90 days before the date you need keys. In the 30 days ending September 28, 2026, 185 Near North condos closed in downtown ZIP codes 60610, 60611 and 60654 in a median of 29 days on market, and 60% sold below their last list price. Those numbers reward a buyer who arrives with a shortlist rather than a blank page. Anne Rossley, Managing Broker with Baird & Warner, Gold Coast, has sold Chicago real estate since 1987 and organizes a relocation around questions that data can answer.

Timing: When to Start

How early should I start looking if I am relocating for work?

Plan on 60 to 90 days before your move date. Three facts explain the window. Fannie Mae retired its simplified condo review on August 3, 2026, so a financed purchase in a building of 11 or more units now involves a full review of the association's budget, reserves, insurance and litigation. A closing window under 30 days is one of the riskier choices for a financed buyer in this environment. And Illinois condominium disclosures arrive only after a contract is signed, which leaves your attorney a short window to review them. Starting early gives every step room to finish. Anne Rossley's buyer's guide walks through the sequence, and her downtown buying page explains how the process is managed.

Should I rent first or buy right away?

Both can be right. Renting for the first few months lets you walk a neighborhood in January and again in June, learn the commute and hear a building's elevators and street noise before committing. Buying immediately makes sense when the property type and neighborhood are already clear. Anne Rossley's owning versus renting resource lays out the numbers worth running either way.

Is it better to tour in person or remotely?

Use video tours to cut the list, then plan one concentrated in-person trip for the finalists. Ask to see the lobby, the mailroom, the parking entrance and the view from the unit at the time of day you would actually be home. A short list of five to eight addresses makes a two-day visit productive.

Neighborhoods: Compare Quickly Without Stereotypes

How do I compare neighborhoods quickly without relying on stereotypes?

Replace reputation with four measurable questions, asked of the same property type in the same period:

  • How long does a typical property take to sell (median days on market)?
  • How much inventory is waiting (months of supply)?
  • What is the median sales price?
  • What does the monthly assessment cover, and how is the building run?

Here is that test applied to Near North condos for the 30 days ending September 28, 2026. The Gold Coast closed in a median of 17 days, with a median sales price of $400,000 and 3.0 months of supply. River North took 21 days, with a median sales price of $448,000 and 5.6 months of supply. Streeterville took 41.5 days, with a median sales price of $585,000. Same product, same month, three different profiles. The figures come from Anne Rossley's Near North condo market update. Neighborhoods in that data are assigned by street address, so treat the boundaries as approximate.

Which neighborhoods belong on a first shortlist?

Choose the property type first, then the neighborhood. For condos, start with the Gold Coast, River North, Lincoln Park, Lakeview and South Loop building pages. Their ZIP codes are 60610, 60654, 60614, 60657 and 60605. For single-family homes, Lincoln Park and Lakeview lead the list. In the same 30 days, Lincoln Park closed 20 homes at a median of 6 days on market and Lakeview closed 13 at 7 days, according to Anne Rossley's September 2026 single-family update. Keep those home figures separate from the condo figures above, because they describe different products. To see current inventory, browse Gold Coast homes for sale, River North homes for sale and Lincoln Park homes for sale.

What should I check about a building before I fall in love with a unit?

Ask four things: the monthly assessment and what it includes, whether parking is included, who manages the building, and whether the building is approved for the financing you plan to use. A unit can be perfect while its building quietly narrows your lender options, so confirm financing status before an offer, not after.

The First 30 Days: A Working Checklist

What belongs in week one?

Speak with a lender about financing, decide between a condo and a house, and write down the non-negotiables: commute, parking, outdoor space and in-unit laundry. Those four filters remove more listings than any neighborhood nickname will.

What belongs in weeks two and three?

Tour the same two or three neighborhoods on a weekday at rush hour and again on a Saturday morning. For every condo, request the monthly assessment, its inclusions and the management company. Keep one spreadsheet so every comparison uses the same fields.

What should I expect from the market?

In the same Near North data, 60% of closings sold below their last list price by a median of 4.2%, and one-bedrooms sold in a median of 19 days. A well-priced unit moves quickly, and the negotiating room on the rest is real. Anne Rossley is a focused, energetic advocate for relocating buyers: high-conviction advocacy, tightly managed, low-friction experience.

The Bottom Line on Relocating to Chicago in 2026

Start 60 to 90 days out, compare the same property type over the same period, and let measurable facts replace neighborhood folklore. With 39 years in the business and 540+ transactions, Anne Rossley turns a first-30-days checklist into a short list of buildings worth touring.

Contact Anne Rossley at Baird & Warner Gold Coast | 773-620-5333 | anne@rossley.com | www.annerossley.com for a FREE 2026-27 Market Strategy Session