Debra’s Insight into the Rise of Chicago’s Top 5 Affluent Neighborhoods

Traversing the streets of Chicago’s most affluent neighborhoods for 40 years of my professional life as a realtor and even longer as a resident, I’ve witnessed their ascent from modest beginnings to peaks of glory. This city, rich in heritage and ambition, houses enclaves where luxury is not just a detail but the very fabric of their existence. The transformation of these areas into the wealthiest neighborhoods in Chicago speaks to a narrative of progress and prosperity. Let’s explore these havens of wealth and luxury living, where the city’s rich tapestry of history and modern-day opulence meet.


I first met Lincoln Park in my early 20’s, way back in 1978! Fast forward to 1982, when I opened Baci, Chicago’s first gelateria at the corner of Arlington Ave and Clark St. A few years later, I am a newly minted real estate agent working in the West Loop and Lincoln Park. Fast forward to 2003, when I bought a sweet little frame house on Howe St and planted myself firmly at home.

In 1984, a townhome at 1829 N Orchard sold for $92,000. In 2016, a limestone mansion built on that lot sold for $6.1M. No wonder Lincoln Park is the most sought-after neighborhood in Chicago; there is something for everyone when it comes to housing, and you are the park and lakefront just a few blocks to the east. Easy access to public transport and the highway. Loads of restaurants, shops, and cafes. You can still buy a townhome, though starting prices are now $400,000, and a single family home on Orchard sold for $10M in 2023.

Most Expensive Homes For Sale in Lincoln Park


From the mob and bootlegging to punk rock and one of the largest art scenes in the country to an art and food mecca, River North has proven to be resilient, adaptable, and invigorating. In the early 20th century, River North was known as Smokey Hollow, nicknamed for the billowing smoke blanketing the area in a dark smog. In 1974, thanks to the efforts of commercial real estate developer Albert Friedman, River North turned into the creative and vibrant neighborhood it remains today, home to photographers, art galleries, and advertising agencies and named The River North Gallery District.

The “Great Gallery Fire” in 1989 wiped out most of the gallery district, sending most of the art scene to Wicker Park and Bucktown. But true Chicago spirit, River North is back and claims to be home to the largest concentration of private galleries in the U.S. outside of Manhattan.

When it comes to housing, you can buy an amazing condo with a pool for $6.9M or a gorgeous home for $10K. Back in 1980, you could buy a 1 bedroom condo for $57K! The art galleries are now surrounded by glass, brick, and steel highrise luxury rental and condo buildings.

Most Expensive Homes For Sale in River North


My first apartment was in the Gold Coast at the corner of Stone and Goethe St. I paid about $400 per month for a junior convertible. If I stood on my tiptoes, I could see the lake. That building is now home to the 65 Goethe luxury condos, price range $4M to $14M. Originally called the Astor Street District and named for John Jacob Astor, one of the richest men in the country. Around 1882, after the Chicago Fire, the Palmer family started building one of the first mansions on Lake Shore Drive. Often overlooked when talking about the history of the Gold Coast is the first leather bar that opened in the country in 1958 and smack the heart of the Gold Coast, by Chuck Renslow.

Today, the Gold Coast is one of Chicago most affluent neighborhoods and home to The Gold Coast Historic District and its stunning and architecturally significant mansions and co-op apartments. There are three primary styles to be found: the Queen Anne, the Richardsonian Romanesque and the Georgian revival style. My favorite building in the Gold Coast is the Benjamin Marshall masterpiece, 1550 N State Parkway, where I’ve had the pleasure of selling 3 special apartments.

Most Expensive Homes For Sale in Gold Coast


History has it that this neighborhood was named for George “Cap” Streeter, a gunrunner and squatter, who arrived in Chicago with his wife Maria and ran aground at the mouth of the Chicago River in the late 1800’s. He claimed the sandbar and surrounding area as his own. When Chicago began rebuilding after The fire, Mr Streeter began illegally selling parcels of land as dumping sites. Potter Palmer and other industrialists of the era did what they could to take Streeter’s land but it was decades later that Chicago Land & Trust won the parcel in court in 1928. From its checkered past, Streeterville has come a long way.

In 1984 a condo at 860 N Lake Shore sold for $87,000. In 2023 you can grab a condo for as little as $116,000 and at the top end, $15M+. The neighborhood is now filled with the crown jewel of Michigan Avenue, Northwestern Hospital and University, the Museum of Contemporary Art, and shops and restaurants galore.

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Talk about a neighborhood that has seen a meteoric transformation! My first job after I got my real estate license in 1984 was to work for a development team on one of Chicago’s first 3 loft condo conversion projects - 4ll S Sangamon and 913 W Van Buren. I bought my first condo in 411. As a side note, interest rates were 13%. Oprah’s Harpo studios opened in the late 1980’s. The West Loop was gritty. Between the hookers, pimps, and drug dealers, and the fishmongers and meatpackers, and some amazing restaurants and clubs, the area became known as the Wild West Loop. I loved it. Back in 1984, prices started at $90K or so. Today, 2023, prices in the West Loop range from $162K up to $7M. The fishmongers and meatpackers have been replaced by Google and Tock and some of Chicago’s hottest restaurants, and the list goes on and on. Steel and glass highrises are springing up like daisies. This neighborhood is on fire, but I am nostalgic for that gritty ‘hood I fell in love with.

Most Expensive Homes For Sale in West Loop

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