Grateful for advice on Investing in the Four Seasons Chicago
Hi đź‘‹ this is our first post. We found a beautiful 3 bedroom unit in the Chicago Four Seasons that we would like to buy and rent (cash buy).
Would love advice on:
1. demand for long term furnished rentals in the gold coast.
2. worries about Chicago following NY's lead and taxing 2nd homes.
3. Appreciation outlook for the gold coast area?
4. Any rumors that anyone has heard on this building? (This actual property has been on the market for 70 days. The asking price is down 30% from 2023.)
Thank you.
PS - we enjoy luxury rentals for the 15 days per year vacation plus capital appreciation. We would love cash flow, but break even is fine.
Most Popular Reply
Great first post and honestly a very solid market to be looking in. The Gold Coast and buildings like the Four Seasons attract a very specific type of renter and buyer, so you’re already in a strong segment.
On furnished long term rentals, there is definitely demand in that area. You’re typically attracting executives, corporate relocations, medical professionals, and international tenants who want turnkey living. The key is that it has to be done right. High-end furniture, clean design, and a true luxury feel. Those units can command a premium, but they also need to match the building and the expectations of that tenant profile. If it feels even slightly mid-tier, it will sit.
Short term rentals are also something you should seriously consider in that building. The Four Seasons operates as a condotel, which means rentals are allowed and that gives you flexibility a lot of other luxury buildings in Chicago don’t offer. That’s a big advantage.
Demand in that area is not just driven by tourism. Yes, you have the lake, shopping, restaurants, and all the downtown activity, but there’s also a strong business and medical component. Northwestern Memorial Hospital is right there and has been ranked the number one hospital in Illinois for years, with national recognition across multiple specialties. That brings in doctors, traveling nurses, specialists, and families visiting loved ones who often prefer a private, high-end stay over a hotel. That type of demand is consistent and not seasonal.
On top of that, Chicago has events happening year-round. Conferences, conventions, festivals, and corporate travel all keep that area active. So whether you’re looking at short term, mid-term, or long term furnished rentals, there’s a steady stream of tenants when the unit is positioned correctly.
From a regulation standpoint, Chicago still allows short term rentals with proper registration and compliance. It's much more flexible compared to New York, where short term rentals under 30 days are heavily restricted unless the owner is present. That puts you in a better position here because you have options on how to operate the unit depending on your strategy. On the concern about Chicago following New York with second home taxes, it's a fair question and something investors are watching. Chicago is already a higher tax environment, so you want to underwrite your deal assuming taxes and HOA could increase over time. If the numbers still work under those assumptions, you're in a much safer position.
For appreciation, the Gold Coast has historically been more of a stability play than a rapid appreciation play. Prime location, consistent demand, but the luxury condo segment has softened a bit, which is likely why you’re seeing that price reduction. That doesn’t make it a bad deal, it just means your entry point matters.
The fact that it's been on the market for 70 days and is down 30 percent is where I would really lean in. In a building like that, units typically move when priced right. That could be an opportunity, or it could mean there's something specific about the unit or the financials. I would take a close look at the HOA, reserves, any upcoming assessments, and how similar units in that building are performing.
Buying cash gives you strong negotiating power, just make sure you’re not overpaying for a luxury asset that could take time to move later.
For context, I’m a mortgage broker with over 25 years in the mortgage and real estate space. I live in the area and have done a lot of business in the Gold Coast working with real estate investors and condotels, so I’m very familiar with how these buildings perform and what to watch for.
If you want, I can take a look at that specific unit with you, break down realistic rental scenarios across short term and long term, and help you structure it the right way whether you keep it all cash or decide to leverage it later. That usually gives you a much clearer picture before moving forward.