Where I’d Buy in Chicagoland Right Now: 5 Chicago Neighborhoods and 5 Suburbs With Real Investment Upside

Real estate investors love asking one question:

“Where’s the next hot area?”

Which is usually code for:

“Where can I buy before everyone else discovers it, before prices go completely insane, and ideally before the coffee shop starts charging $9 for something called a lavender cloud latte?”

As of June 2026, Chicagoland is still a very interesting market. Prices have not crashed. Buyers are still dealing with higher mortgage rates. Inventory is still tight in many areas. And affordability is still a major issue.

According to Redfin’s May 2026 Chicago housing market update, the median sale price in Chicago reached approximately $379,900, up 5.4% year over year.

So no, the market is not exactly throwing a clearance sale in the middle of the street.

But that does not mean buyers and investors have no opportunity. It just means you have to be smarter.

The best investment areas are not necessarily the cheapest places. Cheap does not automatically mean good. Sometimes cheap means “bring a contractor, a therapist, and possibly a priest.”

The better question is:

Where do affordability, location, rental demand, transportation, housing stock, and long-term resale potential all come together?

Here are 5 Chicago neighborhoods and 5 suburban towns I’d be watching closely right now.

Top 5 Chicago Neighborhoods to Watch

1. Albany Park

Albany Park continues to be one of the most interesting investment neighborhoods on the North/Northwest Side.

Recent Redfin market data showed Albany Park home prices were up approximately 21.0% year over year over the three months ending April 2026, with a median sale price around $417,000. Redfin also reported March 2026 prices up approximately 15.3% year over year, with a median sale price around $400,500.

That is a big number. Not “I found a $20 bill in my winter coat” big. More like “wait, why did everyone suddenly realize this neighborhood exists?” big.

Why is Albany Park so attractive? Because it has the magic combination investors love: public transportation, rental demand, diverse housing stock, and relative affordability compared with nearby neighborhoods like Lincoln Square, Ravenswood, North Center, and Logan Square.

Albany Park is not some sleepy hidden secret anymore, but it still feels like one of those areas where buyers can get more for their money than they can in several surrounding neighborhoods.

You have Brown Line access, a strong rental base, great food, multi-unit buildings, single-family homes, condos, and a neighborhood that still has room to grow.

Also, the food scene is ridiculous. If you buy there and gain 12 pounds, do not blame the real estate market.

Investment angle:Albany Park is strong for long-term rental demand, owner-occupant house hackers, 2-flats, condos, and buyers priced out of more expensive North Side neighborhoods.

2. Bronzeville

Bronzeville has one of the strongest long-term upside stories in the city.

Recent Redfin market data showed Bronzeville home prices were up approximately 25.0% year over year in March 2026, with a median sale price around $305,000.

That kind of year-over-year jump gets attention. It also means buyers need to be careful. A neighborhood can have major upside and still require very smart property selection.

Bronzeville has historic architecture, proximity to downtown, lakefront access nearby, public transit, and a deep cultural identity that gives the neighborhood real staying power.

For investors, Bronzeville can be especially interesting because it still offers opportunities at price points that are lower than many North Side neighborhoods, while still being close to major employment centers, the lakefront, public transportation, and downtown Chicago.

That said, this is not a neighborhood where you blindly buy anything with four walls and a roof and call yourself Warren Buffett.

Bronzeville is very block-by-block. You need to understand pricing, condition, rental demand, resale comps, and where development is happening.

Investment angle:

Bronzeville is a strong long-term play for buyers who want historic housing stock, rental potential, and upside — but you absolutely need local guidance before jumping in.

3. Portage Park

Portage Park is one of those neighborhoods that keeps getting more attention because it offers something many buyers want but cannot always afford closer to the lake: space.

Recent Redfin market data showed Portage Park home prices were up approximately 5.1% year over year in March 2026, with a median sale price around $475,000.

That is a healthier, steadier type of growth. Not as dramatic as Albany Park or Bronzeville, but still very strong for a neighborhood that already has a lot of established buyer demand.

Portage Park offers classic Chicago bungalows, brick 2-flats, single-family homes, decent yards, garages, and a neighborhood feel that appeals to both owner-occupants and investors.

It is also a great example of a neighborhood that is not “cheap” anymore, but still looks practical compared with areas that have gone completely off the rails.

A buyer who wants a house in Lakeview may need a financial miracle. A buyer who wants a house in Portage Park may still need a strong pre-approval, but at least they may not need to sell a kidney on Facebook Marketplace.

Investment angle:Portage Park is a good fit for long-term holds, single-family rentals, 2-flat buyers, and house hackers looking for stable demand on the Northwest Side.

4. Humboldt Park

Humboldt Park is one of the more complicated neighborhoods on this list — and that is exactly why it belongs here.

Recent Redfin market data showed Humboldt Park home prices were up approximately 9.8% year over year over the three months ending April 2026, with a median sale price around $535,000. Redfin also reported March 2026 prices up approximately 15.2% year over year, with a median sale price around $530,000.

That tells us the neighborhood is still moving upward, but not in a completely irrational way. In investor language, that can be interesting. In normal human language, that means: “Maybe there is still opportunity, but please do not just buy the first building with exposed brick and vibes.”

Humboldt Park has already seen major price growth in many pockets, especially because of its proximity to Logan Square, Wicker Park, Ukrainian Village, and West Town. But even with that growth, there are still areas where buyers may find opportunity.

The park itself is a major amenity. The location is strong. The housing stock is varied. And demand from renters and buyers remains very real.

However, this is not a “buy anything anywhere” situation. Humboldt Park can change dramatically from one block to the next. One block can feel like a great long-term investment. Another block can make you wonder if your GPS is mad at you.

Investment angle:Humboldt Park is a higher-upside, higher-research neighborhood. It may work well for investors who understand block-by-block pricing, renovation costs, rental demand, and long-term appreciation potential.

5. Avondale

Avondale is not the secret it used to be.

The secret left years ago, probably on a scooter, holding a craft beer.

Recent Zillow data showed Avondale’s average home value at approximately $519,328, up 6.1% over the past year, as of May 31, 2026. Zillow also reported homes in Avondale going pending in around 6 days.

That is fast. Very fast. That is “you saw the listing during breakfast and it was under contract by lunch” fast.

Avondale still deserves attention because it has a powerful combination of location, transportation, housing stock, restaurants, and spillover demand from Logan Square.

For buyers priced out of Logan Square, Roscoe Village, North Center, and parts of Lakeview, Avondale still offers a compelling alternative. It has Blue Line access nearby, expressway access, multi-unit buildings, condos, single-family homes, and a growing reputation as one of the more desirable Northwest Side neighborhoods.

Investment angle:

Avondale works well for buyers looking for long-term appreciation potential, rental demand, and proximity to some of the city’s hottest neighborhoods without paying the absolute highest prices.

Top 5 Suburban Towns to Watch

1. Berwyn

Berwyn is one of the most obvious suburban investment plays near Chicago.

Recent Redfin market data showed Berwyn home prices were down approximately 3.4% year over year over the three months ending May 2026, with a median sale price around $374,776.

Now, before anyone panics and throws their laptop into the alley, a year-over-year decline is not automatically bad for investors. In fact, that can sometimes be where opportunity starts.

A market that has pulled back slightly may give buyers more room to negotiate, especially if the long-term fundamentals are still strong.

Berwyn is close to the city, has a ton of vintage brick housing stock, offers more space than many Chicago neighborhoods, and attracts buyers who want affordability without moving 97 miles away and pretending their commute is “not that bad.”

Berwyn has bungalows, 2-flats, single-family homes, and a dense, city-like feel. It is especially appealing for buyers who are priced out of Chicago neighborhoods but still want access to the city.

It is not perfect. Property taxes matter. Condition matters. Block-by-block research matters. But Berwyn continues to be one of the first suburbs I’d look at for investors who want proximity to Chicago.

Investment angle:

Berwyn is strong for long-term holds, small multi-unit buildings, single-family rentals, and buyers who want city access with suburban pricing.

2. Brookfield

Brookfield is one of my favorite practical investment suburbs.

Recent Redfin market data showed Brookfield home prices were up approximately 3.6% year over year over the three months ending May 2026, with a median sale price around $394,764.

That is not explosive growth, but it is healthy. And healthy is good. Healthy does not make headlines like “prices up 900% because everyone wants to live next to a taco place,” but healthy can be exactly what a long-term investor wants.

Brookfield has Metra access, cute housing stock, a real community feel, and one of the best amenities in the western suburbs: Brookfield Zoo.

It also benefits from being near more expensive areas like La Grange, Riverside, and Western Springs. When buyers get priced out of those towns, Brookfield often starts looking very attractive.

That is the real estate equivalent of being the normal person standing next to someone wearing a $7,000 jacket. Suddenly, you look extremely reasonable.

Brookfield has a mix of bungalows, ranches, two-stories, and smaller homes that may work well for buyers looking for value in the western suburbs.

Investment angle:

Brookfield is a strong long-term suburb for buyers who want Metra access, neighborhood charm, and proximity to higher-priced communities.

3. Skokie

Skokie is one of the strongest north suburban value plays.

Recent Zillow data showed Skokie’s average home value at approximately $426,036, up 6.3% over the past year, as of May 31, 2026. Zillow also reported homes in Skokie going pending in around 8 days.

That is solid growth for a suburb that already has strong demand.

Skokie has great access to Chicago, strong buyer demand, shopping, restaurants, parks, public transit options, and proximity to the North Shore without full North Shore pricing.

That last part is important.

Because once you start looking at certain North Shore towns, your budget may start sweating.

Skokie appeals to a wide buyer pool: families, commuters, downsizers, first-time buyers, condo buyers, and people who want to be close to Chicago without paying Chicago prices or Evanston/North Shore premiums.

Investment angle:

Skokie is strong for stable resale demand, rental demand, condos, townhomes, and single-family homes with long-term buyer appeal.

4. Des Plaines

Des Plaines is an underrated northwest suburban investment town.

Recent Zillow data showed Des Plaines’ average home value at approximately $349,129, up 5.8% over the past year, as of May 31, 2026. Zillow also reported homes in Des Plaines going pending in around 9 days.

That is a very respectable increase, especially for a suburb that still offers relatively attainable pricing compared with some nearby northwest suburbs.

Des Plaines has Metra access, proximity to O’Hare, relatively attainable prices, and a wide mix of condos, townhomes, and single-family homes.

For buyers who want the northwest suburbs but cannot quite make the numbers work in Park Ridge, Arlington Heights, Mount Prospect, or Glenview, Des Plaines can become very attractive.

It also has a practical, commuter-friendly location. And in real estate, practical is not boring. Practical pays the bills.

You know what is boring? Buying something “exciting” that has negative cash flow, surprise repairs, and an HOA that acts like it runs a small country.

Investment angle:

Des Plaines is a strong choice for investors looking for attainable pricing, rental demand, commuter access, and long-term suburban stability.

5. Villa Park

Villa Park is one of those west suburban towns that still feels like it has room to run.

Recent Zillow data showed Villa Park’s average home value at approximately $354,427, up 6.0% over the past year, as of March 31, 2026.

That is a strong number for a suburb that is still more affordable than many nearby west suburban options.

Villa Park is close to Elmhurst, Lombard, Oak Brook, and major job and retail corridors. It has good transportation access, relatively approachable pricing, and a lot of buyers who start looking there after realizing Elmhurst may require either a larger budget or a winning lottery ticket.

Villa Park has single-family homes, smaller homes, starter homes, and investment opportunities that can make sense for the right buyer.

It may not have the same name recognition as some nearby suburbs, but that can be part of the opportunity.

Sometimes the best investment is not the town everyone is already bragging about at a barbecue.

Investment angle:Villa Park is a strong “before it gets too expensive” suburb for buyers who want west suburban access without paying the highest prices in the area.

Quick Market Snapshot

Here is how these areas stack up based on recent year-over-year data:

Chicago Neighborhoods

Albany Park: Up approximately 21.0% year over year over the three months ending April 2026

Bronzeville: Up approximately 25.0% year over year in March 2026Portage Park: Up approximately 5.1% year over year in March 2026

Humboldt Park: Up approximately 9.8% year over year over the three months ending April 2026

Avondale: Up approximately 6.1% over the past year as of May 31, 2026

Suburban Towns

Berwyn: Down approximately 3.4% year over year over the three months ending May 2026

Brookfield: Up approximately 3.6% year over year over the three months ending May 2026

Skokie: Up approximately 6.3% over the past year as of May 31, 2026

Des Plaines: Up approximately 5.8% over the past year as of May 31, 2026

Villa Park: Up approximately 6.0% over the past year as of March 31, 2026

The important thing to remember is that a bigger percentage does not always mean a better investment.

Sometimes a huge year-over-year increase means the area has major momentum.

Sometimes it means you may already be late to the party.

And sometimes a slight decline, like Berwyn’s recent year-over-year number, can mean buyers may have a better shot at negotiating — especially if the long-term location and housing stock still make sense.

In other words, do not buy based on one statistic.

That is how people end up owning a property they found on a spreadsheet but would never want to visit after dark, during rain, or after seeing the basement.

Honorable Mentions

Forest Park

Forest Park deserves attention because it has walkability, Blue Line access, Madison Street restaurants, and proximity to Oak Park and River Forest.

It can be a very interesting alternative for buyers who like Oak Park but do not love Oak Park prices or taxes.

Evanston

Evanston is not exactly a bargain, but it has lakefront access, Northwestern University, transit, restaurants, rentals, and long-term demand.

If you buy well, Evanston can be a very strong long-term hold.

Woodlawn and South Shore

These areas can offer major upside, especially with continued attention around the South Side and the Obama Presidential Center area, but they require careful, block-by-block analysis.

There can be opportunity, but this is not the place to wing it because you saw one TikTok video and suddenly decided you are a developer.

The Big Takeaway

The best investment areas in Chicagoland right now are not necessarily the cheapest areas.

They are the areas where several things line up:

• Buyers still see value

• Renters still want to live there

• Transportation makes sense

• Housing stock has long-term appeal

• Nearby areas are more expensive

• There is still room for improvement and appreciation

In other words, the goal is not to buy the cheapest house in the cheapest area.

The goal is to buy the right property in the right location at the right price with the right plan.

That is where investors win.

And that is also where a good Realtor matters — because “this seems like a deal” and “this is actually a deal” are two very different sentences.

One makes you money.

The other makes you call three contractors, your lender, your attorney, and possibly your mother.

Thinking About Buying or Investing in Chicagoland Real Estate?

Whether you are looking for a Chicago 2-flat, a suburban rental property, a first home, a house hack, or just trying to figure out where your money actually goes the furthest, I can help you compare neighborhoods, suburbs, numbers, rents, resale potential, and red flags.

I’m Jason Rosenberg, a Chicagoland Realtor serving Chicago and the entire Chicagoland area.

Full-Service Real Estate. Lower Commission. Better Results.

Call/Text: 312.882.9797

Website: www.jasonrosenbergrealestate.com

Sources

This article used recent public housing market data available as of June 2026 from Redfin and Zillow. Market data changes frequently, and median sale prices, average home values, inventory levels, days on market, and year-over-year percentages can shift month to month.

Chicago Market Data

Redfin reported that the median sale price in Chicago reached approximately $379,900 in May 2026, up approximately 5.4% year over year.

Source: Redfin — Chicago, IL Housing Market Update: May 2026 https://www.redfin.com/blog/chicago-il-housing-market-may-2026/

Chicago Neighborhood Data

Redfin reported that Albany Park home prices were up approximately 21.0% year over year over the three months ending April 2026, with a median sale price around $417,000. Redfin also reported March 2026 prices up approximately 15.3% year over year, with a median sale price around $400,500.

Source: Redfin — Albany Park Housing Market https://www.redfin.com/neighborhood/34764/IL/Chicago/Albany-Park/housing-market

Redfin reported that Bronzeville home prices were up approximately 25.0% year over year in March 2026, with a median sale price around $305,000.

Source: Redfin — Bronzeville Housing Market https://www.redfin.com/neighborhood/35129/IL/Chicago/Bronzeville/housing-market

Redfin reported that Portage Park home prices were up approximately 5.1% year over year in March 2026, with a median sale price around $475,000.

Source: Redfin — Portage Park Housing Market https://www.redfin.com/neighborhood/30954/IL/Chicago/Portage-Park/housing-market

Redfin reported that Humboldt Park home prices were up approximately 9.8% year over year over the three months ending April 2026, with a median sale price around $535,000. Redfin also reported March 2026 prices up approximately 15.2% year over year, with a median sale price around $530,000.

Source: Redfin — Humboldt Park Housing Market https://www.redfin.com/neighborhood/32139/IL/Chicago/Humboldt-Park/housing-market

Zillow reported that Avondale’s average home value was approximately $519,328, up approximately 6.1% over the past year, as of May 31, 2026.

Source: Zillow — Avondale Chicago, IL Housing Market https://www.zillow.com/home-values/269573/avondale-chicago-il/

Suburban Market Data

Redfin reported that Berwyn home prices were down approximately 3.4% year over year over the three months ending May 2026, with a median sale price around $374,776.

Source: Redfin — Berwyn Housing Market https://www.redfin.com/city/1485/IL/Berwyn/housing-market

Redfin reported that Brookfield home prices were up approximately 3.6% year over year over the three months ending May 2026, with a median sale price around $394,764.

Source: Redfin — Brookfield Housing Market https://www.redfin.com/city/2231/IL/Brookfield/housing-market

Zillow reported that Skokie’s average home value was approximately $426,036, up approximately 6.3% over the past year, as of May 31, 2026.

Source: Zillow — Skokie, IL Housing Market https://www.zillow.com/home-values/20514/skokie-il/

Zillow reported that Des Plaines’ average home value was approximately $349,129, up approximately 5.8% over the past year, as of May 31, 2026.

Source: Zillow — Des Plaines, IL Housing Market https://www.zillow.com/home-values/17761/des-plaines-il/

Zillow reported that Villa Park’s average home value was approximately $354,427, up approximately 6.0% over the past year, as of March 31, 2026.

Source: Zillow — Villa Park, IL Housing Market https://www.zillow.com/home-values/7703/villa-park-il/

Important Note

This article is intended for general educational and market discussion purposes only. It is not a guarantee of future appreciation, rent growth, investment returns, or resale performance. Real estate investment decisions should be based on property-specific analysis, condition, location, financing, rental numbers, taxes, insurance, and current market conditions.