Moving to Chicago and want to Invest

Antonio Ward Jr · 2026-03-11T09:44:05-07:00

Hello,So my partner and I are moving to Chicago. For context, We have 3 doors currently in Michigan (2 rented out and 1 we are living in with the intentions to rent once we move). I am a travel nurse and relocating to take on a full time position in new role and my partner has a tax accounting internship for the summer and then plans to transition into a part time role afterwards. We have been looking at investing in the multifamily market of Chicago with the goal of acquiring a triplex or quad. I have a decent amount of capital saved up from my W2 approx 30K currently. I was thinking of using the FHA strategy since I would quality to use the loan product due to me relocating. After obtaining the property we live in one unit and rent the other two units out by the room. I guess my question is do you guys see any critiques to this strategy? What are some neighborhood or areas we should focus our market research in on? Have you invested in the Chicago market? Appreciate any tips and insight during this transition!

Caleb Brown

Real Estate Agent · Kansas City · Member since 2018 · 4k+ posts · 3k+ votes

7mo

Welcome to BiggerPockets. There's a couple solid agents there that should chime in on the area. Strategy wise I don't see anything wrong. You already have 3 doors from doing this so it'll work. I think going for the 3 or 4 unit would be a step up from a single family but same fundamentals.

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Derek BrickleyBusiness Member

Lender · Ann Arbor, MI · Member since 2021 · 676 posts · 229 votes

7mo

Hey Antonio!

As long as it's for employment reasons and over 100 miles definitely could work well. Depending on credit score and the full situation, the 5% down conventional can help too since there isn't a self sufficiency requirement but chances are in that price range you'd be okay either way. Also depends on debt to income ratio too though which one might make more sense. Either way definitely on the right track, if it's helpful to go through some more details though feel free to reach out

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Jay Kauffman

Real Estate Agent · Chicago, IL · Member since 2015 · 2 posts · 2 votes

7mo

Congratulations on your new role and welcome to Chicago! I made that move from Michigan 16 years ago, so I understand the adjustment that's coming. Buying a 3-4 unit building with a 5% loan may be doable with 30k, but you will be limited to certain areas of the city. FHA is unlikely to work for a 3- or 4-flat due to the Self-Sufficiency Rental Income rule. Don't discount the 2-flats though, especially if it has a non-conforming unit. There are a lot of those and they've been appreciating rapidly the last few years, and with your numbers it'll open you up to more neighborhoods. My team specializes in mult-units and house hacking (we're all house hackers!), so feel free to reach out if you want to go over some scenarios.

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Aaron ZimmermanBusiness Member

Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes

7mo

Welcome. I'd consider a 5% conventional down product instead. As Jay said, FHA is going to be challenging with self sufficiency on 3 and 4 units.

I'd encourage you to listen to the straight up Chicago investor podcast as well for useful tips and come to some networking events when you move here!

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Jonathan KlemmBusiness Member

Moderator

Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes

7mo

What's up @Antonio Ward Jr and welcome to Chicago the Windy City!

100% you should house hack and find a 2-4 unit multi-family. Depending on which neighborhoods you are looking at, it may be easier to find a 2-unit so you don't have to follow the self-sufficiency test.

You may not often cash flow well, but knowing you are buying in a quality area where you'd want to live and paying less than you'd pay in rent is a win!

I followed the exact same strategy. I'd also consider the Homestyle renovation loan product if you are considering doing some rehab, which can greatly increase your equity position.

Happy to make some connections and introductions for you.

Also, highly recommend checking out the local Chicago meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...

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Paul De Luca

Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes

7mo

@Antonio Ward Jr

House hacking is a great strategy for building your portfolio in Chicago. Use an FHA loan or 5% down conventional loan and build a large seller credit into your offer to reduce your cash to close and keep more money in reserves. While you can get more seller concessions with an FHA loan (up to 6% of the purchase price), in practice it will be difficult for you to find a legal 3-4 unit property that passes the FHA self-sufficiency test. If you really want to get an FHA loan I would suggest targeting a legal 2-flat with a finished attic or basement unit (SST doesn't apply to legal 2-units). Otherwise, the 5% down conventional loan is a more attractive option since that doesn't have the SST.

I'm sure @Zack Karp would be open to answering any questions you have about financing strategy.

As for neighborhoods to target, I would suggest connecting with a lender to understand your budget and then from there you can focus on the neighborhoods that make sense for you.

I'm a 4-time house hacker myself and work with a lot of house hackers so if you have any questions, let me know.

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Eudith VacioPro Member

Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes

7mo

Hey @Antonio Ward Jr 👋🏽

Chicago has an abundance of multi-family properties, so you can definitely find a 3-4 unit property. You just have to decide which neighborhood you want to invest in, Chicago is generally divided between the south and north side going east / west. I love the south side of chicago where you can find cheaper inventory and cashflow really well. Its where I invest in and it's worked out well for me!

Definitely recommend going the conventional route because most 3-4 units don't meet the self sufficiency test with an FHA loan.

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Zack KarpPro Member

Lender · Schaumburg, IL · Member since 2015 · 833 posts · 774 votes

7mo

@Paul De Luca thanks for the tag!

@Antonio Ward Jr happy to help answer any mortgage financing questions and map out a game plan for you.

I will also echo what others here have said, Conventional might be a challenge because not only will you need the 5% down plus closing costs, but also 6 months reserves on the new mortgage payment, plus reserves of 2% of the existing mortgage balance of your property in MI. If you have a 401K/retirement/investment account that helps a lot with covering the reserves.

FHA will be tough on legal 3-4 unit properties because of the self-sufficiency test in most areas of Chicago. But one thing Chicago has a lot of are legal 2-unit properties with additional income streams (garden unit, attic, garage, etc). And 2-units are not subject to the SST. That would be the play IMO.

Feel free to reach out, I'd be happy to hop on a call to discuss your numbers or any other questions you might have. Been doing mortgages for 28 years, investors and house hackers are my niche, and I've worked with a lot of travel nurses too so I understand that dynamic.

Best of luck!

847-387-5513

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V.G JasonPro Member

Investor · Member since 2022 · 3k+ posts · 3k+ votes

7mo

$30k for downpayment or does that include reserves for your other properties?

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Henry Lazerow

Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes

7mo

I house hack in Rogers Park. I love the area, and rents have gone up around 10% year-over-year for the last few years so the area is growing. I work with many house hack clients, primarily along the blue line is popular, for example logan square, west bucktown, avondale. These areas have lower prices then east of highway neighborhoods but you can still significantly increase the rents with a cosmetic rehab. Average MLS rents get bumped up 30-50% once throw in white cabinets, white stone, SS appliances, refinish floors and paint so is a huge boost to cashflow. That is the strategy I always recommend clients use. $30k may get you a downpayment but for these Chicago 100 year old multi unit buildings, it's ideal to have extra money for repairs and updates or at least some reserves. For financing FHA does not work unless you want a 2 unit due to something called the self sufficiency test, also FHA looks weak so you will not get a good deal in our very competitive 2-4 unit market. Most of my clients use 5-10% down conventional financing, which is also what I used at 5% to buy my 4-unit house hack.

Happy to chat more, feel free to send me a PM.

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Michael Eskenasy

Investor · Pacific Northwest · Member since 2026 · 538 posts · 309 votes

7mo

Antonio — you’re already ahead of most people just by thinking about house hacking your next move instead of trying to jump straight into full-time investing.

A couple strategic thoughts based on what you wrote:

First, the $30K capital number matters less than how resilient the deal is once you’re in it. Chicago 2–4 unit buildings are often 80–120 years old, and the first surprise repair can wipe out thin reserves quickly. I’d spend as much time stress-testing maintenance and vacancy scenarios as you do looking at the purchase price.

Second, the room-by-room rental strategy can work well in certain neighborhoods (especially around transit or universities), but it changes the management profile of the property. You’re effectively operating something closer to shared housing rather than a traditional multifamily rental. That can increase income potential, but it also increases turnover and coordination.

Third, the 2-flat strategy people mentioned above is actually underrated in Chicago. A lot of the best house hacks in the city are legal 2-units with an additional garden or attic unit that provides extra income without triggering some of the financing constraints on 3–4 units.

One thing I’d strongly recommend while you’re researching neighborhoods is paying attention to how ownership patterns look block-by-block. In Chicago, two streets that look identical on paper can behave completely differently depending on whether the buildings are primarily owner-occupied, investor-owned, or long-held family properties.

That ownership structure often tells you more about stability and tenant quality than headline rent numbers.

Your plan is directionally solid — the biggest thing will just be making sure the first property is financially durable, not just barely workable on day one.

Welcome to Chicago and good luck with the move.

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John Clark

Member since 2018 · 1k+ posts · 1k+ votes

7mo

For best value look at the southwest side of Chicago. Follow the Orange Line.

West Lawn (NOT Wood Lawn) and West Elsdon are good but starting to get pricey. Wood Lawn, Bronzeville, are expensive. Brighton Park, Archer Heights, McKinley Park, are getting to be fully priced.
.
North side of Chicago is expensive. Northwest side is fully priced but you won’t lose money.

Another option is following the Green Line.

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Piotr Senkow

Real Estate Agent · Chicago, IL · Member since 2026 · 13 posts · 12 votes

6mo

@Antonio Ward Jr - lots of great advice in this thread already, especially on the FHA self-sufficiency test and the 2-flat-with-garden-unit strategy. One thing nobody's mentioned that will directly affect your numbers: tax exemption lapse.

Most owner-occupied multifamily properties in Cook County have a Homeowner Exemption on the tax bill, and many older owners also have a Senior Exemption or Senior Freeze.

When you buy the property, those exemptions disappear. The tax bill on the MLS listing is the seller's bill - yours will be higher.

Here's a real example. This 2-flat in Auburn Gresham is listed at $289,900 with a $1,484/yr tax bill

The current owner has Homeowner and Senior exemptions. When those lapse after the sale, the projected tax jumps to $2,743/yr - almost double. That's $105/mo in cash flow you'd lose if you underwrote the deal using the listed tax amount. On a house hack where margins are already tight, that can be the difference between a deal that works and one that doesn't.

Most spreadsheets don't catch this because they just use the MLS tax number. Scroll to the investment analysis section on that listing - it flags the lapse automatically and shows you the projected tax. Worth checking on any property you're seriously evaluating.

At $30K with 5% down you're realistically looking at the $250-350K range after closing costs and reserves. The south side neighborhoods people mentioned have the most 2-4 unit inventory in that range. Good luck with the move - Chicago's multifamily stock is the best in the country for house hacking.

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Moving to Chicago and want to Invest

Moving to Chicago and want to Invest

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