Grateful for advice on Investing in the Four Seasons Chicago
Member since 2026 路 1 post 路 3 votes
Grateful for advice on Investing in the Four Seasons Chicago
Most Popular Reply
Lender 路 Chicago, IL 路 Member since 2025 路 204 posts 路 101 votes
5moGreat 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鈥檙e already in a strong segment.
On furnished long term rentals, there is definitely demand in that area. You鈥檙e 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鈥檛 offer. That鈥檚 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鈥檚 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鈥檙e looking at short term, mid-term, or long term furnished rentals, there鈥檚 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鈥檙e seeing that price reduction. That doesn鈥檛 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鈥檙e not overpaying for a luxury asset that could take time to move later.
For context, I鈥檓 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鈥檓 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.
9 Replies
- Lender 路 Chicago, IL 路 Member since 2025 路 204 posts 路 101 votes5mo
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鈥檙e already in a strong segment.
On furnished long term rentals, there is definitely demand in that area. You鈥檙e 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鈥檛 offer. That鈥檚 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鈥檚 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鈥檙e looking at short term, mid-term, or long term furnished rentals, there鈥檚 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鈥檙e seeing that price reduction. That doesn鈥檛 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鈥檙e not overpaying for a luxury asset that could take time to move later.
For context, I鈥檓 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鈥檓 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.
- Real Estate Agent 路 Chicago, IL 路 Member since 2017 路 2k+ posts 路 2k+ votes5mo
Hi Sandi! No worries about Chicago doing 2nd home taxes like NY, everything has to go through IL which thankfully has many protections against those type of policies (why we do not have rent control, etc.). Gold coast is a nice area but has actually lagged the rest of chicago in growth as you see in the 30% lower price and I would expect very slow appreciation and even potential depreciation of the ever increasing HOA buildings there. I would strongly recommend go for Old Town or Lincoln Park instead and buy a house or 2-4 unit not a condominium, these areas the rents and prices go up steadily every year with high demand we often have bidding wars for both rentals and sales in these areas all 700+ class A tenants and vacancy runs under 3%. Sold a 3 there last year got $150k over ask. Maybe a luxury 2 or 3 unit there could be a good fit!
Not sure what the person posting above is talking about but Chicago does NOT allow non-owner occupant Airbnb, only way to be approved for Airbnb license is if you state you are living in the unit and the address must be on your ID which city requires you to upload a photo of in order to renew the license. They have cracked down on this since 2 years ago with very few exceptions such as some commercial areas or if you have a 5+ unit building you own entirely then can do one unit as an Airbnb. You can do furnished 30+ day rentals if the HOA allows but many require 12 month leases. With a 2-4 unit or house can of course always do monthly furnished rentals as long as 30+ days to avoid the STR laws.
If ever want to chat about Chicago more feel free to shoot me a PM!
- Lender 路 Chicago, IL 路 Member since 2025 路 204 posts 路 101 votes5mo
@Henry Lazerow This is The Four Seasons. It's a Condotel..... It鈥檚 basically like owning an Airbnb, but inside a Four Seasons Hotels and Resorts property. All Condotels have this program where the owner/investor add their unit to the hotels rental pool. Instead of the owner of the condo living there The Four Seasons has a rental program the owner can participate in. Whereas the Hotel manages their guests, bookings, and cleanings, the hotel handles everything for the owner / investor, and their unit gets rented out to travelers just like a high-end short-term rental. They still earn income from the bookings, but there is a percentage after their management and service fees, just like an AirBNB. This is why Condotel鈥檚 are in high demand in Cities like Chicago and Miami. I do these type of deals often.
- Contractor 路 Chicago, IL 路 Member since 2016 路 4k+ posts 路 2k+ votes5mo
Hey There @Sandi Lewis - Welcome to BiggerPockets and love that you are going to invest here in Chicago!
I used to have a Chicago AirBnB, but also moved away from it because of the tight requirements that @Henry Lazerow mentioned. Now you even have to have your ID with the exact address that you are applying for.
@Ebonie Beaco made a good point - if it's down 30% its either one of two things a deal that no one else has seen or a potential problem.
I honestly didn't know you could buy a condo in the four seasons - thats awesome. I'll be on that level some day with you Sandi!
Quality Builders4.966 Reviews - Lender 路 Chicago, IL 路 Member since 2025 路 204 posts 路 101 votes5mo
Yes! There are several Hotels in downtown you can buy condos in and participate in the hotel rental. Some of those hotel's actually market those units on AirBNB and VRBO, in addition to their websites. The benefits is they not only do all the marketing and upkeep of the owners investments, but it also attracts a different type of professional clientele, verses the traditional AirBNB where the owner/investor is fully responsible. Condotels are great for out of state investors, especially those who frequently visit that City where their investment is located in.
- Real Estate Agent 路 Chicago, IL 路 Member since 2017 路 2k+ posts 路 2k+ votes5mo
@Ebonie Beaco wow that is cool! I did not even realize chicago had those thought was more of a FL thing to do the condo hotels. Only issue is the HOA is $3000 a month roughly so likely would not make a very good investment, probably why the price is down 30%.
If it's like the Vegas condotel I looked at. It's also not meant to be a place you ever live personally or rent it out without using them. They double the HOA if you aren't in their rental plan.
You say they list it on Airbnb? Is there anything left after they both take 25-30%?
- Real Estate Broker 路 Chicago, IL 路 Member since 2014 路 2k+ posts 路 1k+ votes5mo
Quote from @Sandi Lewis:
Hi 馃憢 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.One of the reasons I love BP is there's always something new to learn. I wasn't aware of Condotels.
I don't have the data on demand for long term rentals. I'd have to research that but regarding appreciation. The chart below shows that when considering all price points there's been between a 6 to 7% appreciation in condo prices on the Gold Coast. Please note the data below only captures what is sold through realtors.
When just considering condos above $500K depending on the zip code in the gold coast the the appreciation is mixed: In 60610 the appreciation year over year is a solid 7.8%. In 60611 there's been negative growth.
Regarding the Chicago 4 Seasons Hotel- Units have been selling between Several luxury units have been sitting on the market for a while and are taking significant price cuts. At the time of this post you can see one publically listed. There are a few more that are pocket listings, all $1.9M and up.
If you are targeting a unit that is in the $2M range it does not surprise me that the asking price is 30% down since 2023.
- Investor 路 Hendersonville, NC 路 Member since 2016 路 498 posts 路 285 votes5mo
Quote from @Sandi Lewis:
Hi 馃憢 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.If it鈥檚 been sitting 70 days and down 30%, I鈥檇 assume there鈥檚 a reason and go in trying to figure out what you鈥檙e missing, not what you鈥檙e getting.
Gold Coast will always have demand, but long-term furnished is more niche. You鈥檒l get renters, just not as consistently as standard leases, and turnover/management tends to be higher. I wouldn鈥檛 underwrite that aggressively unless you鈥檝e got a really clear picture of who your tenant is.
On the policy side, Chicago already isn鈥檛 exactly landlord-friendly, so I wouldn鈥檛 bank on things getting easier. Doesn鈥檛 mean don鈥檛 do the deal, just make sure it works without appreciation or best-case rent assumptions.
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