r/ChicagoRealEstate

Lived in the suburbs throughout my whole 20’s. Recently got married and debating moving into a single family home (huuuge investment) or selling our current condo in the suburbs and moving to Ravenswood / Andersonville area. Makes the commute longer to work but only by an additional 20ish minutes compared to what I currently do.

I feel like I lost a social group overtime from living in the suburbs all my 20s. We want to start a family in a couple of years but afraid of buying into a $600-700,000 mortgage and missing all city experience. Once you have kids, shit gets real.

Any advice welcomed 💜

My husband and I are in our 50's and becoming empty nesters. Prior to kids, we lived in a 3 flat in Lakeview on the second floor and could hear everything our upstairs neighbor did. Then we were in a high rise apartment and found it very quiet.

We are thinking of buying a condo in a high rise next year because we miss the city and I hear the condos have social events for the residents. I'm looking for community.

I need a building that has concrete floors and something to reduce noise from shared walls. Does anyone live in a building that meets these criteria?

My wife and I are planning on buying on the north side next year. For single families, I'm shocked at how little inventory is available. We're going to revisit in the Winter / Early 2027... but any ideas why so little inventory is available? And any tips on timing?

On one hand, it's a sellers market.

On the other hand, so few are selling ?

(Filtering for any home under $2M. We may be forced into the suburbs... We see less than 20 houses available)

If you are buying a single-family home, condominium, or two-to-four-unit building in Chicago or the suburbs, most of your protection is decided in the first two weeks after your offer is accepted — not at the closing table. Ten issues worth understanding before you write an offer on Illinois residential real estate.

1. What you should have ready before you write the offer

Lender preapproval, proof of funds, earnest money, and an attorney selected before submitting. Attorney-review and inspection deadlines can begin immediately after acceptance. Searching for counsel afterward consumes part of a limited window.

2. The attorney-review provision

Five Business Days is not the whole story. Under the Multi-Board 8.0 contract, the parties' attorneys may approve, disapprove for a reason not based solely on price, or propose non-price modifications within five Business Days after the Date of Acceptance. Business Days means Monday through Friday, excluding federal holidays. The signed contract controls, and it does not automatically disappear at the end of five Business Days.

3. The inspection contingency

Know which option was selected before ordering the inspection. Multi-Board 8.0 includes an inspection waiver, an inspection with specified repair-request and termination rights, and an inspection with a termination right but no right to demand repairs or credits.

4. The mortgage contingency

A preapproval is not final loan approval. The financing contingency should match the loan you are actually obtaining — loan type, financed amount, interest-rate limit, grants, and approval deadline.

5. The appraisal

A financing contingency and an appraisal contingency are not necessarily the same thing. If the property appraises below the contract price, the buyer may have to bring cash, renegotiate, or terminate, depending on the contract and any appraisal-gap provision.

6. Earnest money

There is no universal date when earnest money automatically becomes nonrefundable. Protection depends on the attorney-review, inspection, financing, appraisal, and condominium-document contingencies — and on whether the required notices are actually served before the applicable deadlines.

7. Buying a condominium

A condominium buyer is buying the unit and entering a financial relationship with the association. Review the declaration, bylaws, rules, insurance, reserves, financial statements, litigation, rental restrictions, anticipated projects, unpaid assessments, and special assessments. Under section 22.1 of the Illinois Condominium Property Act, the association must furnish the statutory resale information within ten business days after a written request. Ask the seller to start that process immediately.

8. Buying a two-to-four-unit building

A two-flat, three-flat, or four-flat is also an operating rental property. Review every written lease, verbal tenancy, rent payment, security deposit, delinquency, prepaid rent, tenant dispute, and notice. Under the Multi-Board 8.0 Multi-Unit Addendum, the seller generally must provide specified lease and tenant information within five Business Days after the Date of Acceptance.

9. Title, survey, and the final walk-through

The title commitment identifies recorded matters affecting ownership or use — liens, easements, restrictions, judgments. For non-condominium property, the survey can reveal encroachments, boundary problems, and improvements crossing legal lines. Under Multi-Board 8.0, the seller pays for the owner's title policy and the survey; the buyer pays for the lender's title policy if financing, and the recording fees on the deed. These are contract defaults and can be modified by rider, ordinance, or condominium rules. The final walk-through is not a second inspection — it confirms the property remains in the required condition, agreed work was completed, included items remain, and unwanted property was removed.

10. What a buyer actually brings to closing

On a $400,000 Chicago purchase, buyer closing costs commonly run $5,500 to $8,000 — the city transfer-tax portion, the lender's title policy, recording fees, and lender origination and prepaids. Cash to close typically runs several thousand dollars higher than transfer taxes, recording, and attorney fees alone. Ask for a written estimate early rather than at the closing table.

Bottom line: the best time to protect a buyer is before the offer is submitted. The next-best time is immediately after acceptance, while the contingencies are still open.

Prepared by Lysinski & Associates P.C. — Established 2003 · Chicago, Illinois General information about Illinois residential real-estate transactions. Not legal advice concerning any particular property or contract.

I knew it was not going to be easy but looking for a condo in Chicago has been much harder than I thought. It’s like there is no inventory at all. It seems the only way to get a decent looking property for a good price is to go really far south which I’m not trying to do. I think I went into this whole process a bit delusional about what it was going to cost to get what I was looking for!! I guess I’m looking for a little encouragement and recommendations on neighborhoods that I should be looking in that are within my budget

A bit about me:

First time home buyer
I am working with a real estate agent
Single 30 year old African American women.
Budget $350,000
Salary: $140,000 before taxes
I only have $40,000 to put down. Which in hindsight I know is not a ton.
Looking for 2 beds ideally which I know may be hard.
I have a car.

I was considering Bronzeville for a while but I have been hearing mixed things from friends and family. I want to ensure to choose a location where I’ll be safe and still have access to some city amenities like shops, public transport etc.

I’m thinking of stopping the search for now and waiting another year to save up more for a down payment so I really can get what I want. However, I’m nervous that in this economy if I wait another year that a condo will cost my soul and my first born child(if I ever have a kid). 🤣 If you have bought a home within the last couple years I really commend you cause it ain’t easy out here!

Hi all-

My husband and I both work in Waukegan area and are looking for a single family home on a lake in Spring time, 2027. I am sure options are few and far between, but curious to hear if anyone has recommendations on good motor boat lakes to live on and their experiences. We are trying to avoid the Chain of Lakes, so leaning towards options in Lake Villa (Deep Lake) and possibly Antioch? Budget around 600-750K. TIA

Well, first of all, your Zillow estimate probably isn’t your home’s market value.

Chicago is a city of micro-markets. A condo in Lakeview can behave very differently from a single-family home in Lincoln Park. Even two seemingly identical condos can sell for different amounts because of:

• What floor it's on
• The views
• Outdoor space
• Parking
• Monthly HOA, and what's included
• Building reserves and upcoming special assessments.
• Overall condition of the unit and the building.
• Schools
• Proximity to public transport

Don't make the mistake of looking at active listings. Those don't tell you much. You want to look at closed sale (those tell you where the market was), and contingent sales (where the market is now). If you don't see enough comparable properties, you can also look at cancelled/expired listings. Those give you an insight into a price that didn't work, and therefore you can avoid the same mistake.

The other mistake is relying on automated valuations (Zillow etc). The just look at what 3bed/2bath home sold for and give an average. One could need a gut rehab, and another could have been newly renovated. Those automated valuations can't tell the difference between the two.

If you're trying to estimate value yourself, start with properties that:

1. Sold within roughly the last 3–6 months
2. Are as geographically close as possible
3. Are the same property type
4. Have similar square footage, beds/baths and parking
5. Are reasonably comparable in condition

Then look at the difference!

Chicago homeowners who have recently sold: What surprised you most when you finally learned what your home was worth?

I’ve been thinking about this a lot lately and honestly can’t decide.
On one hand you’ve got rental properties. On the other, starting some kind of business. Both seem like the classic “build wealth / create cash flow” moves people talk about, but I’m curious what the actual experience is like in the beginning.
Do either of them actually put money in your pocket early on, or do they both just eat cash for a while?
Would love to hear from people who’ve done one (or both):
• How long did it take before you saw real cash flow?
• What surprised you the most?
• If you had to pick which would you choose and why?
Just looking for real experiences and opinions. What’s your take?

Mid-30s couple, no kids, both in tech. We're currently in Atlanta and the car-dependence + traffic here has officially killed us. We're both also progressives who have lived in the South and want to get out and try living in a city/state that aligns better with our beliefs and priorities. We're introverts but not shy. We love books, crafting and smaller groups. We're not looking for nightlife.

We're looking for a single-family home with a small yard, and ideally some walkability. Budget is $650-800K. We like independent bookstores and coffee shops, quiet residential streets, and we want a neighborhood that feels like a community and not an entertainment district.

I've been digging into Oak Park and Evanston pretty hard. Both check a lot of boxes on paper. They both have walkable downtowns, good transit, solid indie business scenes. But the more I look at Oak Park the more it feels like it's built for families (great schools, family-oriented civic stuff). We don't have kids and don't plan to, so I keep wondering if we'd feel a little out of place there, or if that's me overthinking it.

Evanston I like a lot culturally. It feels very suited to us, but it's scraping the very top of our budget and the inventory in the area seems tight right now.

So I basically have two main questions:

1. if you live in Oak Park without kids, how has that actually felt, is the family thing overstated or is it real.
2. Are there other Chicagoland neighborhoods or nearby towns we should be looking at? Walkable, detached SFH in budget, progressive, low-key, not a ton of nightlife. Open to city or suburb.

Appreciate any honest takes. Thanks!

With climate change bringing such wild weather here on a consistent basis, I'm wondering how important covered, off street parking will be moving forward. With such a frequent threat of hail, flooding, damage from trees, etc., I don't think I'd want to make a long-term investment in a home without it.

Looking to move to Lincoln Park/Lakeview at the start of October. I saw all the horror of lines out the doors for rentals in these areas and was curious if this is still the case? (no I am not looking at other neighborhoods, I work in Lakeview and would like to bike or walk). Anyone have any experience either as a renter or landlord? Thank you!

What's something you feel like your neighborhood misses out on? I live in a pretty secluded area and miss being able to walk to places.

I'm curious how much of an increase in your insurance premiums have gone up compared to last year. I live in a 3 unit condo building and our building's insurance premiums have gone up by 21% this year (this is insurance that covers the building and not my individual unit). The year before that, the insurance premiums went up by 25%. Our building is 7 years old and has never had any claims.

Would love to hear if others are experiencing the same thing. The sticker shock is definitely making me reach out to insurance brokers to find new coverage.

I’ve been seeing a lot of people say “once you hit 10 doors you can retire.” Some treat it like a hard rule, others say it’s way more complicated and depends on a bunch of factors.

From what I’ve gathered, it seems to come down to things like whether the properties still have mortgages or are mostly paid off, how strong the actual cash flow is after all the real-world expenses, the market you’re in, and how much income you personally need to live on. Self-managing versus hiring a property manager also seems to change the picture a lot for people.

I’m still trying to figure out what “enough” actually looks like in practice.

• How do you personally think about the number of doors needed for retirement or financial freedom?

• What’s been more important for you — nr of door count, cash flow quality, or getting properties paid off?

• Anyone already at a point where their rentals cover (or almost cover) their living expenses? What does that look like day-to-day, and how many doors got you there?

• Any big surprises or lessons that changed how you view the “10 doors” idea?

I know this is a long shot but kinda desperate. Looking for a needle in a haystack in Chicago:

Currently living in lakeview east and want to be closer to downtown. Not really picky on location, just want to be slightly lower south. Looking at Old Town, Gold Coast, Lincoln Park, and Streeterville.

Looking for a studio or 1 bedroom under $2k per month.

For a studio, I want to have enough room to have a couch and bed, not just a bed. I’m only interested in the floor plans that have the kitchen somewhat in its own space, not right on top of the bed area.

Would absolutely love to have hardwood instead of carpet.

24/7 doorman/nice building in general is a huge plus.

I feel like at this point the only way I’ll find something is a sublease or condo rental of sorts from someone because I’m def looking for something more higher end but on a budget? Thoughts or ideas?? Don’t flame me plssss

Was originally thinking of moving earlier but due to some unforeseen circumstances we’re still here until November. I’m trying to decide if I should still sell in the off peak season(maybe still hot in this market) vs renting for 6 to 18 months and listing again during a better season.

Hello Chicago Real Estate community!

I'm a rising junior studying Math and Economics at a liberal arts, and I've spent the last year proving that real estate is the right path. I've done finance internships, Tuck Business Bridge Program at Dartmouth, and now the ULI Foundations in Real Estate (FoRE) certificate.

I'm reaching out to see if anyone would be open to chatting about a learning opportunity for Summer 2027, or just about the industry in general. I'd love to learn more about different paths within real estate and the people who've built careers here.

I don't have direct real estate experience yet, but I'm a fast learner, proactive, and eager to bring real value to a team while developing my technical skills.

Happy to share my resume if anyone's willing to take a look.

Thank you for reading, and for any time or advice you're willing to offer!

We have a 3 bed 2 bath in Hyde park. It's 200k and we make 240k gross but creeping up on 300-305k gross. It's our first place and we wanted to move in 5-7 years to a single family 4 bedroom with a little more room.

I'm wondering if it's just Worth hanging out where we are and pay this condo off and chill for a bit. I look consistently and I typically only see single family condos with no true balcony. I wouldn't want our next place to be more than 300-500k.