Everyone has their imperative routines. The kind of coffee you order without thinking. The first thing you do when you walk in the door. The way you settle into a season without even realizing it. These habits, especially the subtle ones, often reflect something deeper about how we live and what kind of environment we feel most comfortable in.
Fall drinks are a good example. Whether you stick to your usual black coffee or go all-in on something seasonal, that choice hints at your pace, your preferences, and maybe even the type of home and neighborhood that would actually fit you.
This isn’t meant to be serious matchmaking. But if you’ve ever wondered what your go-to order says about the space you want to come home to - and where that space might exist in Chicago - this list is a fun place to start.
If You Love a Classic Pumpkin Spice Latte:
You want charm, character, and curb appeal
Neighborhood: Lincoln Square
Pumpkin spice fans tend to lean into cozy details, warm design, and a sense of community. You want a home with personality, maybe something with original woodwork or a front porch perfect for fall planters. You’re not drawn to the flashiest listings; you want charm, comfort, and something that feels lived-in in the best way.
Lincoln Square fits that vibe beautifully. Tree-lined streets, family-owned bakeries, and homes with soul. It’s the kind of neighborhood where fall just works.
If You Reach for Hot Apple Cider
You want peace and a connection to nature
Neighborhood: North Park
Cider lovers tend to move at their own pace. You’re not in a rush, and you appreciate quiet moments. Maybe that means a backyard with space to breathe, or at least somewhere you can hear birds instead of buses.
North Park is an underrated gem if this sounds like you. With its proximity to the North Branch Trail and LaBagh Woods, it offers a slice of nature without giving up access to the city. Homes here often come with space to grow, whether that means gardening or just stretching out on a Sunday afternoon.
If You Go Straight to Chai or Herbal Tea
You’re all about calm, clean design, and simple living
Neighborhood: West Town
Tea drinkers tend to lean minimalist, but not sterile. You probably love a neutral color palette, thoughtful design, and some indoor plants that somehow stay alive all year. You want your home to be calm but creative, stylish but not overdone.
West Town could be your perfect match. It’s full of airy lofts, modern renovations, and low-key cafes where you can sip your tea without hearing a single Pumpkin Spice order. You’ll also find a great mix of contemporary architecture and classic Chicago flats with updated interiors.
If You’re Into Spiked Cider or a Fall Old Fashioned
You want a place that’s built for entertaining
Neighborhood: Logan Square
You’re the host. The one with the best glassware, the curated playlists, and a signature cocktail. You want a home that lends itself to open layouts, room to gather, and maybe even a rooftop deck for those freak warm October nights.
Logan Square is made for people like you. It’s lively but still has that residential feel. The housing stock includes classic greystones with updated interiors, modern condos with open kitchens, and spaces that beg for a dinner party or game night.
If You Stick With Black Coffee, No Matter the Season
You’re focused, practical, and not easily swayed by trends.
Neighborhood: North Center
You're not here for gimmicks. While the rest of the city is chasing seasonal menus, you’re ordering your usual and getting on with your day. When it comes to real estate, you value smart investment, solid construction, and neighborhoods that actually feel like neighborhoods.
North Center fits that mindset perfectly. It’s residential, well-kept, and has some of the best schools in the city. The housing stock is a mix of timeless single-family homes, updated two-flats, and newer builds that don’t scream trendy but still offer the quality you're after. It’s a place where people settle in for the long haul (and you’re probably one of them).
Drink Up!
These connections may be playful, but there’s truth to the idea that your habits say something about the space you want to live in. Your ideal neighborhood isn’t just about price points or square footage. It’s about how it feels to live there day in and day out.
The good news? Chicago has something for just about every lifestyle and taste. If you're ready to start looking - or just curious where your favorite coffee order might lead - KlopasStratton would love to help you find your place.
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