Erika and I moved to downtown Chicago 7 years ago to be right in the middle of everything. We’re moving out of downtown now, so I wanted to write up a quick recap of what we love about living in the middle of the 3rd biggest city in the US. (Population list at Wikipedia)
The big thing to understand about downtown: there are no houses.
Downtown residents live in high-rises and condos. (If you think you live in Chicago, and you read this blog, and you can afford your own house, you’re not in Chicago. You live in a suburb. Just because you own a Cubs jersey doesn’t mean you’re in Chicago, buddy.)
Shared-wall downtown buildings mean noise. Older buildings don’t have good noise insulation, so you’ll hear the neighbor’s subwoofer when they watch movies, hear the clinking glasses when they have parties, and hear the kids running around above you. But even in brand-new, well-insulated buildings, you’re still likely to hear noise from the street outside. In our current building, we’re 58 floors up, and we still hear the trains and sirens pretty clearly.

Downtown high-rise residents don’t get a yard. That’s great because you don’t have to worry about mowing grass, picking up leaves, landscaping, or shoveling snow in the winter. That’s not-so-great for dog owners – your dog ends up doing its business on small patches of grass that are heavily trafficked by other dogs. You start to look at dog feet a little differently – Ernie walks on some heavily-peed-on areas.
To some extent, city parks are our yard, and they’re awesome. Chicago and New York City have fabulous, huge downtown parks that put suburb parks to shame.
Your garage isn’t next to your front door. You park your car on the garage floor of the building, and then take an elevator (or a couple of elevators) to get into your apartment. In some buildings, shopping carts are available for you to bring your stuff from the car up to your place, but that’s fairly rare. City dwellers keep a Magna Cart in the trunk of the car to make this easier.
Because shopping is more awkward – especially fighting traffic during rush hour – downtown cities have lots of delivery service options. Peapod and Instacart will deliver your groceries, Caviar and GrubHub will deliver food, Drizly delivers booze, Postmates and Amazon Prime Now will deliver your just-about-anything.
Your garage space is muuuuuch more expensive, too, typically $200-$400 per month. In condo buildings, expect to have to purchase spaces to the tune of $30k-$50k, and they have taxes and HOA dues just like your condo does. In every building we’ve been in, wiring for an electric car simply hasn’t even been available even if you wanted to hire an electrician to do it for you.
You don’t have your own front door to the street. Home dwellers are used to just ordering big items like furniture or TVs, and the delivery guys can show up at any time. Not so in downtown – deliveries have to be arranged ahead of time in specific time windows. You may also have to reserve the loading dock and the freight elevator ahead of time because deliveries aren’t allowed through the front door of the building and the regular (fancy) elevators.

Moving, in particular, can be a pain in the butt. You have to schedule everything in advance. If you’re moving between high-rises, you have to coordinate elevator access in both buildings at the right times. Your reservation isn’t for the whole day, either – typically only 3-4 hour windows, like 9AM-noon – because other people need the elevators too.
Sharing has its advantages, though.
With a shared building come shared amenities.
Some buildings’ home associations vote to charge dues on all the owners, and use those dues for fancy gyms, pools, movie rooms, decks with BBQ gear, and more.
The ultimate amenity: 24/7 door staff. By door staff I don’t mean a doorman – someone who stands at the front door, helps with bags, gets taxis, and makes sure the riff-raff don’t get in. Residential buildings almost never have those (although hotels do.) I mean door staff, aka concierges, which are people who stand inside a building, behind the front desk. Door staff do things like:
- Unlock your unit for you if you lock yourself out
- Can let your dog walker or housekeepers into your unit (based on your OK-to-enter lists)
- Send your dry cleaning or laundry out
- Sign for deliveries if you’re not around
- Accept grocery and flower deliveries and store them in a walk-in fridge room (obviously, not all buildings have stuff like that)
If we ever bought a unit in a downtown building, we’d want a building with door staff at least 9AM-5PM. The drawback of door staff: they add significantly to the ongoing monthly cost of your unit, since the unit owners have to pay the salaries.
How much does all this cost? Your homeowners association (HOA) dues are generally based on the square footage of your unit, so larger units absorb a larger part of the building’s cost. For extreme examples, check out Chicago Curbed’s special on the priciest HOA dues downtown. These are all multi-million-dollar condos, but the HOA dues are $8k+ per month. And it rarely goes down, either – it can go up at any time when the building has maintenance emergencies.
High rises aren’t for everyone, all the time.

I love both the city and country life, but at different times. I like city life for making a living, and country life for retirement. I love sitting on a beach, unwinding, with nobody else around. (Other than the bartender who keeps bringing me drinks, and the cook making the food. They can stay. Everybody else, out.)
While I’m still working, I love the convenience of having anything around at a moment’s notice. I’ve had the chance to experience so many incredible things in Chicago – watching world-class chefs at work, marathon winners zip past, hear amazing concerts – and then just walk a few blocks home, or I can be at the airport and then anywhere in the US with no layovers.
Next, we’re trying a low-rise (3-5 stories tall) a little bit out of downtown near the Ukrainian Village. We lose the door staff, pool, crazy amenities, etc, but we’re still close in enough that we can be at our favorite restaurants in 10-15 minutes.
But while I still can, if you’ll excuse me, I’m going to go downstairs and get a cup of coffee and a freshly baked cookie from The Goddess and the Baker.
13 Comments. Leave new
Whatever happened to San Diego? (Not Carmen Sandiego that is)
Brian – we ended up staying here in Chicago instead. I love San Diego, and we’ll get there eventually.
Interesting post, thanks Brent.
I live in central London, and pretty much everything you’ve said about living in downtown Chicago applies here too. I guess it’s pretty much the same for any major city that you care to mention.
It was good to read someone else’s thoughts on the trade offs between living bang smack in the middle of everything, and living a little way outside.
Thanks! It’s true, yeah – if you move even just a little outside, it totally changes everything.
It’s funny Brent. I was thinking of you this morning before this post went up. Was thinking about our visit in Chicago this past fall and us talking about city life vs rural life and how I’d enjoy the city life. I was thinking about that while doing my chores and realized “nah. green acres really is for me” but I sure do love visiting the City and loved your neighborhood, your yard and your restaurants 🙂
This morning, I fired up the tractor, loaded it up with hay and drove down to the fence gate. I opened the gate up and drove in – a wall of snow that I had made yesterday with the same tractor on either side surrounding me like I was driving into a tunnel. Gently drove forward a few paces shaking the bucket, but not too much it would fall out and I’d have to get down and put the bales back in, trying to tell the cows and sheep “MOVE! I’M GOING TO PUT IT INTO THE FEEDERS!!”. Finally I got there, took out my knife and cut open the bales, putting hay into each of three feeders, stopping to talk to the sheep, cows and goats with little pets along the way (for the ones who don’t mind that sort of thing). Then I walked up to each waterer, broke all the ice and checked the level. Walked inside and fed the pigs and chickens, checked out their waterers, and headed out. Along the way, I stopped at the egg boxes to steal 5 eggs, 3 of which were still quite warm even on this 14 degree morning. Hopped back in the tractor, drove back up and stopped to marvel at all the snow and watch the trees with their snow on them. I don’t have Rick Bayless a walk away(That was such a good meal!!!), but I’m still crazy enough to love having the freezers full of grass fed, well cared for chicken, pork, lamb and beef from the farm.
Of course yesterday, while I was moving all the snow and trying to juggle the time and the hassle of animal feeding chores, I would have traded for a day in a high rise in Chicago 😉
Great post. And great points 🙂
Hahaha, and this morning, I walked Ernie to a cafe. We both had to deal with the animals. 😉
Not in a million years. Too many people. Too much noise. Just too much. I live in the mid-west with lots of wide open space where cost of living doesn’t require me to be a rock star consultant to live comfortably 😉
We chose to live close-in and have a rowhouse on a 20-foot lot. At some point I knew my son would start to question why our house isn’t bigger. The reason is because we are not millionaires. But then he started talking about which “houses” he liked better and he meant the garden apartments his friends live in on the top floor with the cathedral ceilings (actually smaller than our house). It all depends on what you are used to, I guess.
Andrew – hahaha, wow!
Like you he’s kind of interested in the amenities. The door staff, the pool and the game room especially.
I’ve always wanted to live downtown.
Something about the noise and people says, “The world is waiting for you! Get
out there!” Loved being in a downtown condo in Seattle(PASS) and throwing open my windows.
I have to wait for my youngest (10) to be grown and out on her own first. But one day…
Arlene – yeah, it’s really amazing when events happen, too. I’ll just be sitting at home doing stuff, and hear protests going by, or a marathon runs past the house, or people gather to celebrate the Cubs winning. It makes you feel alive!
All those listed Cons are a Huge negative for me, personally. I’m a relatively anal person who gets irritated Easily with other people and their habits and ways. I need my own personal home; downtown condo building living is not for me.
i WAS 50/50 on the edge between either a condo building or home…but now 98% a home.