All Forum Posts by: Tom Casey

I may be biased (yes I am a realtor lol), but I believe that one of the best ways to find good deals is to have an active and attentive boots-on-the-ground and investor-focused real estate agent looking for deals every single day. Most agents will not do the work necessary to effectively help flippers or even understand the numbers/analysis you need to run your business. But when you find one who does, treat them well because they can be your best asset.

Cheers!

@Paul De Luca Thank you! @Howard Maidens please take a look at my recent forum post here https://www.biggerpockets.com/topics/1062934

Let me know if you have any other questions and I’d be happy to help!

Awesome, looking forward to it! We need more of these in Chicago!! Thanks for hosting

Oh Ben, how did I forget the PIZZA!! There are so many good options, it really all just comes down to personal preference. My personal favorite is Pizzeria Uno (they also have Pizzeria Due), not the biggest crowd pleaser but I love their style. Another one of my favorites is called The Art of Pizza. Theirs is more the traditional style, like Giordano's on deliciousness steroids. People will tell you that Lou Malnati's is the best, but honestly you'll do better with the ones I mentioned. But I'm one of the few Chicagoans who actually likes Giordano's more than Lou Malnati's. 

But anyway, so many good options. I didn't even mention some of the fan favorites like Pequod's, and there is even a deep dish pizza pot pie in Lincoln Park! You kinda can't go wrong and the fun is all in the adventure finding your personal favorite. Cheers!

Hey Ben!

House hacking in Chicago is a great way to break into the market. If you're looking to stay no more than 30 minutes from Streeterville with traffic, Cicero might be a stretch. East Garfield Park, Tri-Taylor, and United Center area are all up-and-coming neighborhoods right off of 290 where you can find some MFR buildings that pencil out numbers-wise. I'd also recommend keeping your eye on a few off of 55, like Heart of Chicago, McKinley Park, Pilsen, and Bridgeport. Also, a few good options in near south side neighborhoods such as Bronzeville, Kenwood, and Oakland.

Overall, Chicago is very block-by-block and you're going to have good and bad pockets in every neighborhood. I like where your thoughts are to avoid the exorbitant rents of downtown Chicago by househacking. But just remember to have realistic expectations on your initial margins/return. Even with a 3- or 4-unit, your tenants' rent will not cover all of your expenses (PITI + vacancy, maintenance, capex). You'll still be paying something like $1000-2000 for yourself. But that is a beautiful thing because once you move out and rent it out, it will at least breakeven and you will build your net worth immensely. Chicago is an awesome market to invest but you have to be willing to compromise on cash flow in the short term, especially if you have to be close to downtown.

Hope that helps and happy to talk more. Let's connect!

Hey Frank!

I live and specialize in downtown Chicago! Tons of options close to downtown under $200K. Seasonally, you're looking at an excellent time to be buying as well, especially as we get into October and November. Would love to connect and help you find something that fits your needs.

So lately A TON of clients have approached me with the idea to buy an STR (Airbnb, Vrbo, etc) in Chicago, usually downtown or close to city center. The conversation almost always goes something like, "I'm looking for a one- or two-bed unit close to downtown that I can Airbnb out whenever I want and then use for myself when I'm in town." Sounds great doesn't it? On paper, the numbers for this are amazing, home run for sure! But as most of you probably know, nothing truly great in this life comes easy... and Airbnbs in Chicago are no exception to that rule. Here's what should be top of mind when thinking about STRs and MTRs in or close to downtown:

First and foremost, 99.9% of condo associations in Chicago do not allow short-term rentals. Even the ones that do usually limit minimum lease terms to 31+ days. There are specifically two full amenity buildings downtown that allow 31-day short term leases. Those are 30 W Huron and 545 N Dearborn. The prices are pretty high in these buildings though and oftentimes the numbers aren’t going to pencil out unless you’re buying cash as an appreciation play.

So if condos aren’t really a good option (without having to break the rules), what’s next?

Next option would be multi-unit buildings. These are going to give you a little more freedom because there won't be any association to worry about. However, you're still going to face some limitations/roadblocks here. For one, by Chicago STR regulations, you are only allowed 1 Airbnb/STR for 2-4 unit buildings and only up to 25% for 5+ unit buildings. Since you'll have to register all your Airbnb units through the City of Chicago, they are likely to catch on if you are not following this rule. Majority of people doing Airbnbs are doing it for one unit and then doing either MTR or normal 12-month leases for the others. However, even this strategy has implications. Technically, the City of Chicago ordinance states that you cannot operate an STR in your building if you're not living in the actual UNIT that is being used as an STR (not just in the building). Though I have some clients who are still operating Airbnb units without living in the actual unit (some don't even live in the same building), these clients are technically breaking the rules according to the ordinance. Will they get caught? Maybe, maybe not... But they're definitely taking on some risk there.

Airbnb/STRs in Chicago are great on paper, but they present a multitude of challenges. The regulations have been becoming more and more stringent and limiting over the years. In my opinion, if you're not too risk-averse, your best option is to buy a multi-unit and Airbnb out one of the units while renting the others out normally (if you can live in one unit, even better!). But I would definitely make sure that it at least pencils out to break even as a standard rental building, so that if the city decides to crack down, you at least have a solid investment property after all is said and done. 

As always, please feel free to reach out with any questions and/or responses. Let's all win together!

Good point @Brie Schmidt, thank you! An agent did mention that to me on a showing, makes it super tough to make it work with ANY building...UGHH. But I do have a few clients who still currently operate Airbnb units that are not owner occupied. Hopefully Airbnb/City of Chicago don't crack down too hard on that aspect of the STR ordinance.

Hey Charles!

I live and specialize in downtown Chicago. Here’s what should be top of mind when thinking about STRs and MTRs in or close to downtown.

First and foremost, 99.9% of condo associations in Chicago do not allow short-term rentals. Even the ones that do usually limit minimum lease terms to 31+ days. There are specifically two full amenity buildings downtown that allow 31-day short term leases. Those are 30 W Huron and 545 N Dearborn. The prices are pretty high in these buildings though and oftentimes the numbers aren’t going to pencil out unless you’re buying cash as an appreciation play.

So if condos aren’t really a good option (without having to break the rules), what’s next?

Next option would be multi-unit buildings. These are going to give you a little more freedom because there won't be any association to worry about. However, you're still going to face some limitations/roadblocks here. For one, I'm told that by Chicago STR regulations, you are only allowed 1 Airbnb/STR for 2-4 unit buildings and only up to 25% for 5+ unit buildings. Since you'll have to register all your Airbnb units through the City of Chicago, they are likely to catch on if you are not following these rules. Majority of people doing Airbnbs are doing it for one unit and then doing either MTR or normal 12-month leases for the others.

Though Airbnb/STRs are great on paper, they do present a multitude of challenges especially in Chicago where the regulations have been becoming more and more stringent and limiting. In my opinion, your best option is to buy a multi-unit and Airbnb out one of the units while renting the others out normally. Once you’re settled in and you get a feel for the market, adjust accordingly.

Hope that helps, and would always love to talk more. Please don’t hesitate to reach out anytime if you have other questions regarding the Chicago market.

Best,

@Keith T Williams try Steve Wrought. He does a great job, has amazing attention to detail. You can reach him at (773) 426-0458