The big three

Homes in New York, LA, and Chicago

Back in February, my friend and I booked a trip to San Francisco. The plan was to rent a car and do a road trip around Northern California. Must-see places included Alcatraz, Lake Tahoe, Yosemite, and Big Sur, among others. The tickets were booked for the end of May.

Looking back now, it seems ridiculous that I was gearing up to board a plane not too long ago. The idea of sitting inside a cramped cabin — breathing in recycled air while a disease that passes through airborne particles ravages our nation and the rest of the globe — gives me crippling anxiety.

Traveling is something that I plan on readily returning to when some semblance of normalcy finds its way back to our planet… whenever that may be. But for the time being, one of the only ways that I can satisfy the travel bug is by looking at real estate in other parts of the country. And sometimes even close to home.

A WFH-friendly apartment in Brooklyn

For a lot of young people, moving into your own place is often a rite of passage into adulthood. This is especially true in places like New York, where the cost of living is extremely high and rent prices are continually on the rise. But after the pandemic hit and many folks began working from home indefinitely, living with roommates suddenly became a way for people to socialize safely in a time when seeing friends is done at a distance and going out in public for leisure is not just frowned upon, but also kind of scary. These days, having a live-in social circle doesn’t seem that bad.

This adorable two-bedroom, one-bath apartment in Brooklyn’s Clinton Hill neighborhood offers a great WFH-friendly loft bedroom. Features of this pre-war unit include hardwood floors, high ceilings, lots of natural light, and a renovated kitchen with a dishwasher. This apartment would be great for two friends to share. The cost is $2,600 per month. [Douglas Elliman]

A Santa Monica stucco beauty

Ahhhh, Santa Monica. Who doesn’t love this beachside city? When I visited LA in October of last year, a girlfriend and I went to a rooftop bar in Santa Monica called Élephante, which had amazing cocktails. It was extremely trendy, with stylish Californians surrounding me in every direction. I was wearing overalls and was very sweaty. I’d happily go there again in sweatpants if it meant I could enjoy another one of their icy cucumber drinks.

This home — originally built in 1932 — is gorgeous. And it has a steep price tag to match its incredible beauty. Living inside of this stucco Spanish-style retreat in Santa Monica is going to cost you $2.8 million. And according to the listing, the taxes on this place cost over $24,000 last year. While the cost that this property incurs seems wildly unattainable to many, there’s nothing wrong with daydreaming about living within its four walls anyway. The 2,230-square-foot home includes four bedrooms, three bathrooms, French oak floors, Carrera marble countertops in the master bathroom, and a guest house out back with a wet bar. [Compass]

A time capsule just outside of Chicago

Speaking of rooftop bars with great cocktails, Chicago is home to my favorite: Cindy’s — right across the street from Millennium Park. I went nearly four years ago and I still remember the cocktail that I had was made with pistachio milk and cost me, like, $16. (By the way, I’ve been to both restaurants mentioned in this newsletter with my very on-trend friend whose talent appears to be knowing the best rooftop bars in every city.)

One of the most enticing aspects of Chicago and the surrounding suburbs is that, out of the three most populous cities in the US, it has the lowest cost of living. If the national average cost of living is valued at 100, Los Angeles is at 173. Manhattan is a whopping 258. But the Windy City’s cost of living is just 107. The downside? Property taxes are some of the highest in the country, so it all sort of evens out in the end.

Designed by John Van Bergen in 1917 — a studio head for the famous Frank Lloyd Wright — this incredible time capsule of a home includes a two-story great room, three bedrooms, and two and a half bathrooms inside 1,700 square feet of living space. The house needs some cosmetic tweaks here and there, but there has been some work done in recent years: The plumbing, electric, roof, bathrooms, and the kitchen have all seen updates. History buffs will love owning a home that has local historic landmark status. The asking price is $599,000. [Sotheby’s International Realty]