If you're standing in a suburban home that's suddenly too big and quiet, and you keep catching yourself daydreaming about a lock-and-leave condo with a lake view, you're in good company. Some of my favorite clients are empty nesters making exactly this move, trading a house with three unused bedrooms and a lawn for the walkability, culture, and simplicity of downtown Chicago condo living.
The most common question I hear at this stage isn't "which building?" It's "should we rent before buying, or just buy?" It's a smart question, and the honest answer is: it depends on you. Below is the same guidance I give clients considering Lakeshore East and the New Eastside, so you can decide with clarity instead of pressure.
Why do some empty nesters rent before buying downtown?
After decades in one home, moving from a large house into a condo isn't just a real estate transaction. It's a lifestyle change. Renting first gives you a low-commitment way to test that change before you make it permanent.
Empty nesters often rent first to:
- Try downtown living on for size. A weekend at a hotel isn't the same as living somewhere Monday through Sunday. Renting tells you whether you love the energy of the Loop and the lakefront, or whether you'd rather be a little quieter.
- Learn the micro-neighborhood. Lakeshore East, the New Eastside, Streeterville, and the West Loop each feel different. Renting lets you find out which one fits your rhythm.
- Get to know the buildings from the inside. You can't fully judge a building's staff, soundproofing, elevators, or amenities until you've lived with them.
- Give themselves room to downsize gradually. Renting removes the pressure to purge a lifetime of belongings in a single frantic month.
When does renting before buying make sense?
Renting first is usually the right call when any of these are true for you:
- You're new to downtown. If you've lived in the suburbs for 20+ years, a year-long rental is a relatively small price for learning what you actually want in a permanent home.
- You're not sure which neighborhood is "yours" yet. Renting in or near Lakeshore East lets you walk to Millennium Park, the Riverwalk, and the lakefront path and see how it feels day to day.
- Your suburban home hasn't sold yet. Renting can keep you from carrying two mortgages or feeling rushed into a purchase to line up closing dates.
- You're downsizing dramatically. Going from 3,500 square feet to 1,400 is a big adjustment. A rental is a forgiving place to figure out how much space you truly need.
- You want to "date" a building before you commit. Some buildings look perfect on paper and feel different once you're living with the elevators, the neighbors, and the assessments.
When might buying right away make more sense?
Renting isn't automatically the safer choice. For plenty of empty nesters, buying directly is the better financial and emotional decision. Buying right away often makes sense when:
- You already know and love the area. If you've spent years coming downtown for work, the symphony, or dinners on the Riverwalk, you may not need a trial run.
- You've found the right floor plan in the right building. Well-designed units in the most sought-after New Eastside buildings don't sit for long. Renting "to be safe" can mean watching the exact home you wanted get bought by someone else.
- You want stability and equity. Renting means a year or two of payments that build someone else's equity. If you're confident in the move, buying puts that money to work for you.
- You're ready to be done moving. Renting first means two moves instead of one. For some people, the emotional cost of moving twice outweighs the flexibility.
- You want to customize. You can paint, renovate, and truly settle into a home you own in a way a lease won't allow.
The real challenge: downsizing from a large house to a condo
Whether you rent or buy, the hardest part is rarely the real estate. It's the downsizing. Moving from a big suburban home into a Chicago condo means making thoughtful choices about what comes with you and what doesn't.
The things that surprise my clients most:
- Furniture that doesn't fit. The sectional, the dining set that seats twelve, the king bed in a guest room. Much of it simply won't work in a condo footprint, or won't fit in the elevator. It helps to measure before you move, not after.
- Storage is finite. Many condos come with a storage locker, but it's smaller than a suburban basement or garage. Seasonal decor, tools, and "someday" boxes need a plan.
- Vertical living is different. Groceries, packages, and pets all move through a lobby and an elevator instead of a garage. It's easier than people expect, but it's a new routine.
- Less to maintain, more to enjoy. The trade-off for all of this is real: no snow to shovel, no roof to replace, no yard to mow. Most empty nesters tell me the freedom is exactly what they were hoping for.
Furniture, storage, and building lifestyle considerations
Condo living comes with a rhythm that a single-family house never had. Before you fall in love with a view, it's worth thinking about how you actually want to live:
- Amenities you'll really use. A pool, fitness center, dog run, party room, and 24-hour door staff sound wonderful, and many are. But amenities drive monthly assessments, so it's worth being honest about which ones matter to you.
- Parking. Downtown parking is often deeded and sold or rented separately from the unit. If you're keeping a car or two, confirm the details early.
- Pets. Buildings vary widely on breed, size, and number of pets. If you have a dog, this can quickly narrow your list.
- Noise, light, and views. A lake view and a city view are very different experiences at 7 a.m. Floor height, exposure, and proximity to Lake Shore Drive all shape daily life.
- Move-in logistics. Most buildings require you to reserve the freight elevator and follow move-in windows. It's a small thing that's much easier when you know it in advance.
Questions to ask before choosing a rental or a condo
Whether you're signing a lease or writing an offer, these are the questions I want my clients to have answers to:
- What do the monthly assessments, or for a rental, the total monthly cost, actually include?
- Are there any special assessments planned or recently completed, and how healthy are the building's reserves?
- What is the building's rental cap or leasing policy? This matters even for buyers, because a building crowded with renters can affect financing and resale.
- How is parking handled? Is it included, deeded, or separate?
- What are the pet, storage, and move-in rules?
- How responsive is building management, and how well is the building run day to day?
- What has actually sold or rented recently in this tier and floor plan, and for how much?
That last one is where guesswork gets expensive. Two units with the same square footage in the same building can live, and price, completely differently based on floor, exposure, and finishes.
Why local building knowledge matters more than the listing photos
Here's the part you can't Google. In Lakeshore East and the New Eastside, the difference between a great decision and a regret often comes down to details that never appear in a listing: which buildings are exceptionally well managed, which have a special assessment on the horizon, which floor plans feel bigger than their square footage, which stacks get the quiet lake view, and which face the traffic on Wacker or the Drive.
I spend my time tracking these buildings specifically: the sales, the rentals, the assessments, the management. That's the knowledge that helps you avoid the wrong unit and recognize the right one when it comes up. Listing photos tell you what a home looks like; local building knowledge tells you what it's like to live there.
Let's figure out the right move for you
There's no single right answer to "rent or buy." There's only the right answer for you, based on your timeline, your comfort with the change, and what you want this next chapter to feel like. That's exactly the kind of conversation I love having.
If you're an empty nester thinking about Lakeshore East, the New Eastside, or downtown Chicago condo living, I'm always happy to be a sounding board. No pressure, and no rush. Whenever the time feels right, reach out to Ginger Menne, even if it's just to talk things through.
Frequently asked questions
Is it better to rent or buy in Lakeshore East as an empty nester?
It depends on your timeline and how familiar you are with downtown living. Renting first makes sense if you're new to the area, still selling a suburban home, or unsure how much space you need. Buying right away tends to make sense if you already know and love the neighborhood, have found the right floor plan, and want to build equity instead of paying rent.
What is the difference between Lakeshore East and the New Eastside?
The New Eastside is the broader downtown Chicago area east of Michigan Avenue between the Chicago River and Randolph Street. Lakeshore East is the newer master-planned neighborhood within it, built around a central park and known for its walkability to Millennium Park, the Riverwalk, and the lakefront.
How much do I need to downsize to move into a downtown condo?
Most empty nesters moving from a large suburban house downsize significantly, often by half or more. The key is planning ahead: measure your furniture against the new space and the building's elevators, and decide what truly earns a place in your next home before you move.
What monthly costs should I expect beyond the mortgage or rent?
Condo assessments, also called HOA fees, typically cover building operations and amenities, and can also fund reserves for future repairs. Ask what's included, whether any special assessments are planned, and how parking, storage, and pets are handled. These vary widely by building.
