The Most Expensive Chicago Neighborhoods: Luxury Living at Its Finest

Located right on the shores of Lake Michigan, Chicago is one of the largest cities in the United States and has a reputation for delivering the very best of the country’s dining, art, culture, entertainment, and architecture. The Windy City is home to a number of neighborhoods, each of which has its own unique feel, go-to restaurants, local shops, and noteworthy attractions. Some of Chicago’s most desirable neighborhoods also happen to be some of the city’s most expensive, but for those looking to relocate to these Chicago neighborhoods, the steep price tag may very well be worthwhile.

Gold Coast

An historic district with charming streets and luxurious homes, Chicago’s Gold Coast is a neighborhood known for its gorgeous architecture, upscale restaurants, and local boutiques. The Gold Coast borders Lake Michigan and residents can delight in the area’s stunning views. The neighborhood’s residences vary in style, but the most noteworthy are the expansive and timeless greystones that have been beautifully maintained over the last century. The Gold Coast has excellent public schools, but is also home to a wealth of renowned private schools. The neighborhood offers a variety of homes in all styles and sizes, from one-bedroom apartments to large single-family homes. While apartments can be priced as low as the high $100s, grand, historic homes in the Gold Coast neighborhood can be priced as high as $15M.

River North

Known for its upscale eateries, trendy nightclubs, and lively bars, River North is one of Chicago’s most bustling neighborhoods, especially after hours. An epicenter of art and design, creative types flock to River North to enjoy close proximity to a multitude of art galleries, historical architecture, and museums. River North is also home to some of the city's most buzzworthy restaurants, and celebrity chefs have been known to set up shop in this must-visit neighborhood. Home prices in the River North neighborhood are indicative of the demand, as studio apartments are priced starting in the mid-$100s and larger homes in luxury buildings are priced as high as $9M.

South Loop

The South Loop is a neighborhood that offers a mix of modern living and historical significance. The area features contemporary high-rises, historic row houses, and loft-style condos. The South Loop is home to cultural landmarks like the Field Museum, Shedd Aquarium, and Soldier Field. Its proximity to Grant Park and the lakefront makes it an attractive option for those who enjoy outdoor activities. The average home price in the South Loop is around $600,000, appealing to both young professionals and families.

Lakeview 

Lakeview offers the perfect blend of urban amenities and neighborhood charm. Boasting a diverse community, it’s known for its lively entertainment scene, including the famous Wrigley Field. The housing market in Lakeview includes everything from historic greystone homes to modern apartments. Residents enjoy a variety of dining options, shopping, and outdoor activities along the lakefront. The Lakeview area’s average home price is approximately $700,000, making it an attractive option for those seeking upscale living with a strong sense of community.

Streeterville

Situated along Lake Michigan and bordered by the Magnificent Mile and Michigan Avenue, it’s hard to find a better location in all of Chicago than Streeterville. Some of the area’s most noteworthy landmarks include the Navy Pier, the East Lake Shore Drive Historic District, and Ohio Street Beach, which extends into Lake Michigan. The neighborhood is also where many of the city’s most impressive skyscrapers can be found, including the famed John Hancock Center, Water Tower Place, and 900 North Michigan Avenue. One bedroom condos in Streeterville are priced starting in the mid-$100s, however grander, more luxurious three and four bedroom homes can fetch prices into the $7M range.

Wicker Park 

Wicker Park is a dynamic neighborhood known for its artistic flair and trendy lifestyle. The area features an array of vintage shops, art galleries, and hip cafes. Residential options include historic homes, modern condos, and stylish lofts. Wicker Park attracts a creative and diverse community, making it one of Chicago's most unique neighborhoods. The average home price here is around $650,000, appealing to those looking for a vibrant and eclectic living environment.

West Loop

What was once an industrial zone has become one of the trendiest, most highly-sought after areas in The Windy City. Chicago’s West Loop is where locals and visitors will find some of the city’s most renowned dining as well as up and coming eateries, right along the famed Randolph Restaurant Row. In addition to world-class cuisine, the West Loop area is home to a wealth of local art, including bold, one-of-a-kind murals that have become neighborhood landmarks. Those looking to relocate to the West Loop neighborhood can expect to pay top dollar, as one bedroom apartments are priced starting in the mid-$200s while larger homes in more modern, luxurious buildings are priced as high as $6M and above.

Bucktown 

Adjacent to Wicker Park, Bucktown shares its artistic spirit while offering a more upscale living experience. The neighborhood is popular among young families and professionals, featuring a mix of historic homes and new developments. Bucktown is known for its independent boutiques, innovative restaurants, and lively nightlife. The 606, a converted rail line turned greenway, provides a scenic outdoor space for residents. Average home prices in Bucktown are approximately $675,000, making it a desirable area for those seeking a balance of creativity and luxury.

Old Town

Beloved for its charming, picturesque streets lined with mature trees and unique shops, Old Town is a neighborhood that residents are excited to call home. The neighborhood features historic buildings, many of which reflect Victorian-era architectural styles. Those in search of a laugh flock to Second City comedy club, a neighborhood landmark and Chicago institution. Old Town boasts a number of quaint coffee shops, old-fashioned pubs, and cute eateries that blend old-world charm with modern city life. The neighborhood offers residents access to excellent schools as well as a wealth of cultural attractions. Prospective homebuyers can expect to pay top dollar for an address in Chicago’s Old Town neighborhood, with studio apartments priced starting in the high $100s and expansive townhomes commanding prices as high as $6M.

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$15,750,000

800 North Michigan Avenue Ph67, Chicago, 60611

6 Beds 8 Baths 9,250 SqFt Residential MLS® # 12118228

Contingent

$13,950,000

14 West Superior Street 7300, Chicago, 60654

3 Beds 5 Baths 6,085 SqFt Residential MLS® # 11702353

$11,700,000

800 North Michigan Avenue Ph64, Chicago, 60611

5 Beds 7 Baths 8,500 SqFt Residential MLS® # 12086519

$11,650,000

65 East Goethe Street 3, Chicago, 60610

7 Beds 11 Baths 12,435 SqFt Residential MLS® # 12142837

$11,000,000

9 West Walton Street 3800, Chicago, 60610

6 Beds 7 Baths 7,500 SqFt Residential MLS® # 12039535

$9,900,000

209 East Lake Shore Drive 14, Chicago, 60611

7 Beds 9 Baths 12,250 SqFt Residential MLS® # 12153665

$8,995,000

800 North Michigan Avenue 63ph, Chicago, 60611

5 Beds 6 Baths 8,400 SqFt Residential MLS® # 12114621

$8,900,000

↓ $600,000

159 East Walton Place Ph, Chicago, 60611

4 Beds 5 Baths 7,880 SqFt Residential MLS® # 11954424

$7,950,000

65 East Goethe Street 3n, Chicago, 60610

5 Beds 7 Baths 8,045 SqFt Residential MLS® # 12142843

$7,950,000

↓ $950,000

500 West Superior Street 2703, Chicago, 60654

3 Beds 6 Baths 10,000 SqFt Residential MLS® # 12085997

$7,500,000

14 West Superior Street 6800, Chicago, 60654

4 Beds 5 Baths 6,085 SqFt Residential MLS® # 12064485

$6,995,000

451 East Grand Avenue Ph66, Chicago, 60611

4 Beds 6 Baths 7,147 SqFt Residential MLS® # 12162907

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