Almost every relocation call I get starts the same way: "What's the best neighborhood?"
I get why you're asking. But it's the wrong first question. Chicago isn't one housing market. It's a string of very different ones, from lakefront condos to century-old suburban estates, sometimes just a few blocks apart. The better question is what your actual day looks like. Do you want to walk to a train, or do you want a yard? Do you want quiet by 8pm, or somewhere that's still loud at 8pm?
There's one mistake I watch relocating buyers make more than any other, and it's not the neighborhood they end up picking. I'll get to it at the end of this post. First, let's walk the map with real numbers.
The North Side condo corridor
If you want to stay close to the lake and keep city life within walking distance, this is where most of my relocation clients start looking.
Neighborhood | Condo Median | Overall Median | Days on Market (Condo) | Days on Market (Overall) |
|---|---|---|---|---|
Lakeview | $500,000 | $550,000 | 27 | 29 |
Andersonville | $497,000 | $550,000 | 14 | 18 |
Edgewater | $276,000 | $300,000 | 47 | 45 |
Lincoln Park | $700,000 | $792,500 | 25 | 29 |
Source: MRED (Chicago's regional MLS), July 2026.
Lakeview, which includes Wrigleyville, is condo-heavy and genuinely lively: coffee shops, the ballpark, and the lake path a few minutes from most front doors. It's usually the first stop I take North Side relocation buyers to, because it tells them quickly whether city-condo life is actually for them. What it's not is quiet. Game days bring crowds, so if you work from home and need silence on a Wednesday afternoon, it's worth walking the block on a weekday before you decide, not just on a Saturday.
Andersonville, inside Edgewater, runs almost identical pricing to Lakeview, but the pace is nothing alike. Homes here average just 14 days on market for condos, 18 for the market overall, some of the fastest-moving inventory on the North Side. If you find something you like here, don't sit on it.
Edgewater as a whole tells a different story: a single-family median around $300,000 and a condo median around $276,000, which makes it one of the more approachable lakefront options on the North Side. It also moves slower, averaging 45 to 47 days on market. That's not a red flag. It usually just means less competition and more room to negotiate.
Lincoln Park is the North Side's most expensive neighborhood, and it's worth being direct about that upfront. Homes here move fast too: condos average 25 days on market, the overall market 29, so a strong offer still matters. What that price buys is the park itself, the zoo, the lakefront, and some of the city's strongest walkability. It's popular with relocating buyers who want city convenience but are also thinking a few years ahead. My advice: compare what you're actually buying, not just the sticker price, square footage, outdoor space, long-term resale strength.
The North Shore suburbs
The North Shore works differently, and this is where relocating buyers get surprised, especially if they only look at one number.
Suburb | Condo Median | Overall Median | Days on Market (Condo) | Days on Market (Overall) |
|---|---|---|---|---|
Evanston | $329,000 | $449,000 | 34 | 33 |
Wilmette | $525,000 | $1,159,000 | 33 | 29 |
Winnetka | $617,500 | $1,995,000 | 21 | 39 |
Source: MRED (Chicago's regional MLS), July 2026.
Evanston is still the most accessible entry point to the North Shore: a lakefront college town, home to Northwestern, genuinely walkable.
Here's the number people get wrong. The North Shore's reputation is built on its single-family estates, and those overall-median numbers are real. But if a condo works for your life, you can be in Wilmette, or even Winnetka, for a fraction of that headline price. Wilmette's overall median is $1,159,000, but its condo median is $525,000. Winnetka's overall median is $1,995,000, but its condo median is $617,500. What you're trading for the lower number is space and a yard, not the town, or the lake. Some relocating buyers want the estate. Others just want the zip code and the quiet, and a condo gets them there for a lot less.
The real mistake to avoid
The mistake I see most isn't picking Lincoln Park over Evanston, or a condo over a single-family home. It's picking a neighborhood off a "best of" list before figuring out your own day, your commute, your noise tolerance, your five-year plan, and then trying to make the numbers fit your life after you've already signed.
Do it the other way. Figure out the day you actually want to live, then let that point you to the neighborhood, and the property type, that actually fits.
Frequently Asked Questions
What's the difference between Chicago's North Side and the North Shore for someone relocating?
The North Side (Lakeview, Andersonville, Edgewater, Lincoln Park) is Chicago proper: city living, walkable retail corridors, and a mix of condos and vintage buildings close to the lake. The North Shore (Evanston, Wilmette, Winnetka) is a string of separate suburban towns north of the city line, generally offering more space and more single-family inventory, with Evanston as the most walkable and urban of the three.
Can you find a condo on Chicago's North Shore for less than a single-family home?
Yes. As of July 2026 MRED data, Wilmette's overall median (which includes single-family homes) is $1,159,000, but its condo median is $525,000. Winnetka's overall median is $1,995,000, while its condo median is $617,500. A condo can put you in either town, with the same lake access, for a fraction of the headline home price.
Which Chicago neighborhood should I look at first if I'm relocating and not sure where to start?
There's no single right answer, it depends on your day-to-day, not a ranking. If you want the liveliest, most walkable condo option, Lakeview or Andersonville are worth starting with. If you want more approachable pricing with lake access, Edgewater is worth a look. If you want space and are comfortable with suburban living, Evanston is the most walkable entry point to the North Shore.
How fast do homes move in these markets?
It varies block to block. Andersonville is currently the fastest-moving market in this group, averaging 14 to 18 days on market. Edgewater is the slowest, averaging 45 to 47 days, which typically means more room to negotiate. Most of the other neighborhoods and suburbs covered here fall in the 25 to 34 day range.
If you're relocating to Chicago's North Side or North Shore and want to walk through this together, book a free consultation with me. Let's keep it calm, even with everything else about a move that isn't.
