r/ChicagoRealEstate

Officially started the home-buying process and my husband and I have a modest budget of $300k for a condo in Chicago (not considering outer burbs). In chatting with our realtor he’s painted a very grim picture lol - can anyone who’s bought within this budget offer some insight? Thanks!!

EDIT: looking for 2 bed specifically, considering fringe/up and coming neighborhoods. Super open to location and we also dont mind needing to upgrade appliances/minor work.

Looking at prices of condos in my neighborhood has me itching to sell. It's honestly insane what places similar to mine are going for right now. There's a part of me that wants to list my place and capitalize on this market.

But I don't.

Because in this market, selling high means buying high. Someone buys my overpriced condo and then I have to buy someone's overpriced house.

I also currently have a 2.6% mortgage rate. Buying with a rate double that makes me cry. My current mortgage is lower than rents for 1br's in my n'hood. Increasing my mortgage payment by so much, even for a SFH, in this economy makes me nervous.

So here I sit.

Anyone else in a similar situation?

I have a rental property that was previously my primary residence. I’ve been renting it for the past 4 years. Unfortunately it’s expected to sell about $50k less than I purchased it for.

I’ve heard there can be tax advantages in situations like this when you go to sell. Can anyone point me to some knowledge resources, calculators, or even just a super high level explanation of my options to not totally lose 50k out of this. I’d like to avoid using a tax consultant if it’s not actually that complicated after I can wrap my head around it.

Editing to clarify this is in River North. …sigh… the only neighborhood that didn’t appreciate in the past 10 years.

I’ve been thinking about this lately as I watch the North Shore market.

For people who own a home and like where they live, what would actually have to happen for you to decide it’s time to sell?

Would it be:

• needing more space
• wanting less maintenance
• a job change
• interest rates dropping
• taxes getting too high
• kids graduating
• finally getting your “dream kitchen”
• a certain price number
• something else entirely

I feel like a lot of people are emotionally attached to their current mortgage rate right now, even if the house itself no longer fits their life perfectly.

Curious what would truly move the needle for you in Northbrook, Glenview, Deerfield, Wilmette, etc. Are you staying put no matter what, or is there a scenario where you’d seriously consider making a move?

Hey everyone,

I’m trying to figure out whether buying makes sense right now or if I should just keep renting. Would really appreciate any thoughts - I’ll be in Chicago with my company for at least 4-5 years, maybe longer, and I’m weighing the pros/cons of pulling the trigger on a 2-bedroom condo with a total monthly cost around $4k–$5k all-in (mortgage + taxes + HOA). I wish a normal mortgage was $3500 or less but welcome to Chicago taxes and hoa as you already know!

The idea would be to live in it for the next several years and then rent it out when I eventually move. Rents for nice 2-beds downtown are already $4k–$5.5k+ and keep going up, so I’m wondering if buying could help lock in costs and build some equity.

Preferred areas: River North, Streeterville, Gold Coast, Old Town — maybe Wicker Park or Lincoln Park if the numbers work.

I’m currently in a 1-bed near the river (rent was $2600 years ago and now $3200…) and would really like a decently high floor with a good view, balcony, and nice windows if possible. I know that pushes the price up and might not be the absolute best investment move (a duplex or something with rental upside could be smarter), but I’m in sales with a busy schedule and don’t have time for big renovations. Want to be downtown near my office/train and looking for move-in ready or close to it.

Chicago’s high taxes, HOA fees, and special assessments are my main worry. Does this overall strategy make sense for someone in my spot? Is buying better than renting long-term, especially with the plan to rent it out later?

Would love any recent experiences with high-rise condos in these neighborhoods, and any strong opinions on how the value will grow over time in say streeterville vs wicker.

What are the biggest things to watch out for (assessments, tenant laws, condo boards, resale, rental market, etc.)?

Any thoughts or data points would be really helpful — thanks in advance!

I'm a new broker entering the Chicago market and trying to figure out the best brokerage/team ft before jumping in.

I'm especially curious about.

. Zillow Flex teams

. mentorship-heavy eXp teams

• boutique brokerages

•and places that are supportive of personal branding/content creation.

For those already in Chicago real estate:

• Where would you start if you were brand new today?

• Which brokerages actually train?

Any teams/ offices that are hidden gems?

Appreciate any advice. Trying to make a smart long-term decision instead of chasing hype.

Thanks!

I’ve been looking at luxury apartments in Chicago, to move to in the fall, and I’m shocked at the reviews I’ve been reading, almost every single one contains problems such as hidden fees, extra charges, package/mail theft, to cars getting broken into while parked on site… list goes on…

I definitely do not want to pay $3100 for a tiny studio only to go through any of the problems I mentioned above.

Any recommendations? I’m a healthcare professional and looking to work in either Rush Hospital, or Northwestern Memorial Hospital, so I want something near downtown Chicago, a studio or a 1 bedroom. Please help!!!

Hi everyone — follow-up question after my earlier post.
A lot of people mentioned that a 3-bed condo or townhome in Lakeview, Lincoln Park, or West Loop around $650k–$700k may not be very realistic.
So I’m trying to better understand the affordability side before adjusting our search.
For people buying in Chicago right now, what does the realistic all-in monthly payment look like for homes nearer to $800k?

I’m thinking all-in as in:
Mortgage
Property taxes
HOA
Homeowners insurance
Other recurring costs I may be missing

Also, what percentage of take-home pay do people feel is actually comfortable for housing in the city right now?
I know there are general rules based on gross income, but I’m more curious about what feels realistic in practice, especially for condos/townhomes in neighborhoods like Lakeview, Lincoln Park, West Loop, West Town, etc.
Would love to hear real examples from recent buyers or people currently house hunting. Thank you!

I’m currently in the process of buying a 1940s Cape Cod in Jefferson Park, and I’m feeling pretty stretched thin with closing costs. My realtor suggested a few addon inspections like raddon testing, a sewer scope, and a chimney cert. At first, they felt like upsells, but after looking into the repair costs, I’m second guessin my skepticism.

From what I’ve gathered, a sewer scope is basically non negotiable. Finding out a pipe is collapsed after you move in could be costly, whereas the scope is relatively cheap. Radon also seems to be a common issue in this region, and since the test is inexpensive and it poses health risks, it feels like a better safe than sorry situation.

I’m considering skipping the chimney inspection since we don't plan on using the fireplace immediately, but I’m curious if that’s a mistake. For those of you who have bought older homes recently, which extras did you pay for? Did anyone skip the sewer scope and end up regretting it, or did you find it was mostly peace of mind?

Hey all,

I property manage and do renovations. I have about 5-10 small work orders a month and have about 2 active projects at all times. I want to hire an individual who knows the trades and can be my right hand. I find myself troubleshooting and managing work orders with contractors and although I don't think I'm financially ready to hire someone I think it's needed in order for me to grow. Im located in the Chicago and was wondering where I am able to find someone like that.

Thanks in advance

I'm recently divorced and need to move out of the 3 flat that I was bought out of by my ex. It feels like prices have skyrocketed since negotiation of the decree and I've screwed myself out of significant equity value. My daughter is going to continue to go to school in Ravenswood and there is simply little to no 2 br inventory that is "affordable" (less than $400k) to a single income. I'm looking at 30% down and losing out to cash offers. I don't mind going a little further neighborhood wise if i can get a space that has a good place for a home office (i wfh) or ideally a 3br, but that inventory is low too and the sold prices get higher every day. I don't want a 20 min drive each way to my daughters school AND be crammed into a too small space. I've been searching and looking at places with my realtor and been out bid. Rent in Ravenswood is also out of hand so I won't fair much better giving up on buying. Just writing to vent and commiserate about how tough it is right now. I tried negotiating to stay in my unit (I'm in the 2nd floor unit he's in the 1st floor unit) while my daughter is young but my ex wouldn't cooperate.

After 11 years selling homes all across Chicago I've watched people light serious money on fire on pre-listing renovations that did nothing for their final sale price.

If you’re thinking about spending $30k or $40k gutting a kitchen before you list, this is for you.

The person buying your home has their own taste and their own contractor. In a market where serious buyers are still waiving inspections to stay competitive, they are walking through fast and making mental decisions on the spot. 

A kitchen renovation based on your taste is not the asset you think it is.

What IS affecting your offers right now is the stuff that tells buyers whether this building is going to cost them money after closing.

Your parapet walls. Chicago's freeze-thaw cycle is brutal on masonry and experienced buyers know it. When buyers are moving fast and waiving inspections, they are not walking through blind. If they see fresh mortar slapped over crumbling brick on the parapet wall, they know what it means. Water is already inside. 

They don't need an inspector to tell them that. They can see it. And the offer reflects it. A proactive tuckpointing job runs $3,000-$5,000 on most north side buildings. The return on that specific spend is hard to match.

Your mechanical room. Buyers who've lost a few offers and are coming in without contingencies go straight to the basement. Furnace date, water heater date, electrical panel.

Your listing photos. Buyers are scrolling at 11pm on their phones. Bad photos of a great home are just a home people skip. Professional photography runs $300-$500. The impact on showing volume is not small.

Spend $8,000 on the right things and you'll recover it and then some. Spend $$ gutting a kitchen and you might break even if the buyer happens to share your exact taste.

Fix the stuff that keeps the water out. Let the buyer pick the paint colors.

Curious what other people have seen on this. Happy to answer any questions in the comments