All Forum Posts by: Daniel Bourdeau

Awesome post and graph. I share the sentiment - when I started seeing Gatlinburg show up on the 'best places to invest' chart in 2022-2023, I knew it was going to lead to an oversaturation. I've largely told investors to stay away - too make investors normalizes and hurts any potential returns there. 

It'll be really interesting to see the correction there take place - I think you are spot on in where in the cycle we are at. I'd say we are entering a lot healthier time to be in STR than the boom and bust of the last few years.

@Everton Souza

Welcome to Chicago!

We have a ton of Real Estate Meetups you should think about attending (Chicago MFH Investors Club. I'm always up to connect with fellow Chicago investors as well, so feel free to reach out!

@Boris Le

Chicago is tough to make it work from a cashflow perspective. A lot of buyers are in it for the appreciation (Chicago should continue to appreciate around 5% this year) rather than cashflow.

IMO, there are limited ways to Cashflow in Chicago. Investors often make it work by doing a 'house hack' where they live in one units and LTR or STR the other half. Being creative like that is how I make the numbers work - with my in-law unit covering most of my mortgage on the whole building.

@Amy Martin Yes, the address on your ID needs to match the unit address (and unit number) if you are applying to a owner-occupied license. I have met plenty of people that 'fake' this, but I think its best to play by the rules to avoid losing a license. 

Chicago can definitely work for STRs, but its highly regulated and as such you need to play within the rules. I've met 100s of STR hosts in Chicago that make it work (myself one of them). The fact that there's stricter regulations just means that less investors are rushing in, and those that remain keep more of the pie.

@Tenzapa Wakombe @Greg Janes 

Seasonality definitely is significant in Chicago. May-September are prime booking months, and outside it of that its really just weekend travelers. Still, I'm not afraid of the seasonality since the summer booking window can make enough to have it make sense. 

@Amy Martin I'm an owner occupant in Chicago in a SFH with an in-law suite - it goes really well for me! Feel free to reach out if you have more questions

Hey all — just wanted to share some quick thoughts from my experience running a short-term rental here in Chicago and why I think more people should be paying attention to the Midwest.

I’ve been house hacking a 2BR in-law unit in Portage Park (NW side, not touristy) for the past 2.5 years. It pulls in about $32k a year, covers most of my mortgage, and has been a great way to build wealth. I also manage some Luxury ground up builds in Colorado, but this is my 'live for almost free' strategy.

Here’s why I think this kind of setup works really well here:

1. Chicago’s tough rules actually work in your favor
Chicago's short-term rental rules are strict — licenses, insurance, 2-night minimum, ect. Most important: in most cases it needs to be your primary residence (unless its in a larger building with less than 25% currently as airbnbs AND legal in the HOA). That knocks out a ton of out-of-town investors

A lot of hosts fake the “primary requirement” thing, but they’re technically breaking the rules. Since I actually live here and rent out the lower unit (which isnt technically another 'unit', I’m 100% compliant — and I’m not competing with a flood of illegal or high-volume operators. Way less saturation if you do it by the book. I will say it looks highly lucrative for the investors renting out 5/6BR homes with solid amenities, although legally dubious and not possible to launch multiple listings.

2. Midwest pricing still makes sense
Compared to places like Florida, Texas, or Tennessee — where inventory is surging and it’s turning into a buyers market — Chicago’s still solid. Inventory is super low here, which is keeping upward pressure on prices. Reventure.app is forecasting about 5% appreciation in 2025, and we’re still in seller’s market territory. That stability gives me confidence in the long-term value of the property.

Plus, entry prices here are still reasonable, and the rental demand is strong enough that the numbers actually pencil out. That mix is getting harder to find.

3. There’s demand, even outside the “hot zones”
I’m not in downtown or a trendy area, but I still stay booked. I get tourists, business travelers, folks visiting family or coming in for events. It’s steady. Summers are obviously busier, but winter doesn’t completely die — I’ve learned how to price and plan for the seasonality.

If you’re thinking about getting into STRs and like the idea of house hacking or finding something low-key that still cash flows, I think Chicago (and the Midwest in general) deserves a look. I’m a local realtor alongside a property manage and help people find these kinds of setups — happy to connect if you’re looking into it.

Anyone else running a house hack STRs in less obvious markets? Would love to hear what’s working for you.

Hey all — just wanted to share some quick thoughts from my experience running a short-term rental here in Chicago and why I think more people should be paying attention to the Midwest.

I’ve been house hacking a 2BR in-law unit in Portage Park (NW side, not touristy) for the past 2.5 years. It pulls in about $32k a year, covers most of my mortgage, and has been a great way to build wealth without having to go full “Airbnb mogul.” I also manage some Luxury ground up builds in Colorado, but this is my 'live for free' strategy.

Here’s why I think this kind of setup works really well here:

1. Chicago’s tough rules actually work in your favor
Chicago's short-term rental rules are strict — licenses, insurance, 2-night minimum, ect. Most important: in most cases it needs to be your primary residence (unless its in a larger building with less than 25% currently as airbnbs AND legal in the HOA). That knocks out a ton of out-of-town investors

A lot of hosts fake the “primary requirement” thing, but they’re technically breaking the rules. Since I actually live here and rent out the lower unit (which isnt technically another 'unit', I’m 100% compliant — and I’m not competing with a flood of illegal or high-volume operators. Way less saturation if you do it by the book. I will say it looks highly lucrative for the investors renting out 5/6BR homes with solid amenities, although legally dubious and not possible to launch multiple listings. 

2. Midwest pricing still makes sense
Compared to places like Florida, Texas, or Tennessee — where inventory is surging and it’s turning into a buyers market — Chicago’s still solid. Inventory is super low here, which is keeping upward pressure on prices. Reventure.app is forecasting about 5% appreciation in 2025, and we’re still in seller’s market territory. That stability gives me confidence in the long-term value of the property.

Plus, entry prices here are still reasonable, and the rental demand is strong enough that the numbers actually pencil out. That mix is getting harder to find.

3. There’s demand, even outside the “hot zones”
I’m not in downtown or a trendy area, but I still stay booked. I get tourists, business travelers, folks visiting family or coming in for events. It’s steady. Summers are obviously busier, but winter doesn’t completely die — I’ve learned how to price and plan for the seasonality.

If you’re thinking about getting into STRs and like the idea of house hacking or finding something low-key that still cash flows, I think Chicago (and the Midwest in general) deserves a look. I’m a local realtor alongside a property manage and help people find these kinds of setups — happy to connect if you’re looking into it.

Anyone else running STRs in less obvious markets? Would love to hear what’s working for you.

I manage a STR in Unincorporated Jefferson County (Coal Creek Canyon) and lived there for a while. I'm happy to answer any questions about the licensure process for Jefferson County. They are indeed in the process of revising it. Its indeed quite a tedious and onerous process (in addition to expensive) in unincorporated Jeffco compared to other areas, but its generally friendly to non-primary residence STRs

Scale those number up to a 50%, 100% or 200% increase in supply and you'll see where the problem lies.

Not every market is a city. In remote areas, Long-Term housing is already extremely difficult to find, and they're not readily available commutable areas. You seem to be minimizing this problem.

Building short-term rentals is only marginally more expensive than acquiring existing structures. You can build a primary residence with 5 or 10% down, and you can build an investment property for the same 20% down ( plus some construction interest) that's you can acquire it for. It's far less 'elitist' and out of reach than you say. 

We've already seen some legislation propose this year restricting large entities from acquiring single family residences, and if I were a betting man, I assume that this trend will continue and it'll be harder and harder to acquire and make money off of single family residences.