Where should you live in Chicago?
Twenty honest guides from a team that sells in every one of these neighborhoods - what each actually feels like, what homes cost as of 2026, and who it suits. When you want the block-level truth, ask Hollis or call (312) 766-9073.
Lincoln Park
North Side · lakefrontLincoln Park is Chicago's classic north-side neighborhood: leafy streets of greystones and brick three-flats between the lake and the Chicago River branch, anchored by the free Lincoln Park Zoo, the park itself, and DePaul University.
$300Ks condos to $2M+ single-familyLakeview
North Side · lakefrontLakeview is Lincoln Park's bigger, slightly more affordable northern neighbor - a huge lakefront neighborhood that contains Wrigleyville, Southport Corridor, and Boystown (Northalsted).
$200Ks condos to $1.5M+ single-familyLogan Square
Northwest Side · the boulevardsLogan Square is the Northwest Side's cultural engine: historic boulevards lined with greystones, a nationally known restaurant scene on Milwaukee Avenue, and one of the strongest appreciation stories in Chicago over the last decade.
$300Ks condos to $1M+ single-familyWicker Park
West Town · the six cornersWicker Park is Chicago's original creative-turned-prime neighborhood: the six-corners intersection of Milwaukee, North, and Damen anchors boutiques, restaurants, and nightlife, while the side streets hold some of the city's most striking Victorian mansions and workers cottages..
$300Ks condos to $2M+ single-familyBucktown
West Town · north of the 606Bucktown is Wicker Park's quieter northern twin: same six-corners access to restaurants and nightlife, but leafier side streets, more single-family homes, and a family-forward feel.
$300Ks condos to $2M+ single-familyWest Loop
Near West Side · Fulton MarketThe West Loop is Chicago's fastest-transformed neighborhood: former meatpacking blocks now hold Restaurant Row on Randolph, the Fulton Market office district (Google, McDonald's HQ), and a wave of luxury condo and apartment towers.
$300Ks condos to $3M+ penthousesSouth Loop
Downtown south · museum campusThe South Loop puts the lakefront, Grant Park, and the Museum Campus at your doorstep for meaningfully less than River North.
$200Ks condos to $1M+ townhomesRiver North
Downtown · gallery districtRiver North is downtown Chicago's classic high-rise neighborhood: full-amenity condo towers, the gallery district, Michigan Avenue shopping next door, and the river walk below.
$200Ks studios to $3M+ penthousesGold Coast
Near North · historic lakefrontThe Gold Coast is Chicago's marquee address: landmark mansions and vintage co-ops between Michigan Avenue and the lake, Oak Street Beach at the end of the block, and the city's most storied residential architecture.
$200Ks vintage co-ops to $5M+ mansionsOld Town
Near North · historic triangleOld Town is the historic triangle between the Gold Coast and Lincoln Park: crooked pre-fire streets, Second City comedy, Wells Street's restaurant row, and some of the most charming single-family blocks in the city.
$300Ks condos to $3M+ single-familyLincoln Square
North Side · Giddings PlazaLincoln Square is the North Side's favorite grown-up neighborhood: a walkable European-flavored square at Lincoln, Lawrence, and Western, the Old Town School of Folk Music, Giddings Plaza's summer concerts, and calm residential blocks that families rarely leave once they land..
$200Ks condos to $1.5M single-familyRavenswood
North Side · Metra corridorRavenswood is the quiet achiever between Lincoln Square and Andersonville: leafy residential streets, the Metra corridor's brick industrial buildings turned breweries and lofts, and some of the most reliable family-home value on the North Side..
$200Ks condos to $1.3M single-familyAndersonville
Far North Side · Clark StreetAndersonville is Chicago's most beloved main-street neighborhood: the Swedish-heritage Clark Street strip of independent shops, bakeries, and restaurants, one of the country's most established LGBTQ+ communities, and blocks of well-kept vintage homes that rarely hit the market..
$200Ks condos to $1.5M single-familyEdgewater
Far North Side · lakefrontEdgewater is Chicago's most affordable lakefront neighborhood: beaches at Foster and Kathy Osterman, vintage high-rises along Sheridan with lake views at condo-in-the-suburbs prices, and the Bryn Mawr historic district's Art Deco streetscape..
$100Ks condos to $1.2M single-familyUptown
North Side · entertainment districtUptown is the North Side's live-music neighborhood - the Aragon, the Riviera, and the Green Mill jazz club - wrapped around Montrose Harbor, Montrose Beach, and some of the best lakefront parkland in Chicago.
$100Ks condos to $1M+ single-familyAvondale
Northwest Side · next in lineAvondale is where Logan Square's energy is heading: the same Milwaukee Avenue spine one stop further out, a Polish-heritage housing stock of brick two-flats and cottages, and a restaurant scene growing fast around Belmont and Milwaukee.
$200Ks condos to $900K single-familyIrving Park
Northwest Side · historic districtsIrving Park is the Northwest Side's quiet architecture showcase: the Villa District's Prairie-style bungalows, Old Irving Park's Victorian farmhouses on oversized lots, and a commuter's dream position on the Blue line, Metra, and the Kennedy - all at prices below the lakefront neighborhoods..
$200Ks condos to $1M single-familyHyde Park
South Side · university · lakefrontHyde Park is the South Side's intellectual capital: the University of Chicago campus, the Museum of Science and Industry, Frank Lloyd Wright's Robie House, Jackson Park and the coming Obama Presidential Center - plus a lakefront housing market that delivers space and architecture at prices the North Side cannot match..
$100Ks co-ops to $1.5M+ historic homesPilsen
Lower West Side · arts districtPilsen is Chicago's Mexican-American cultural heart and its most vibrant arts neighborhood: 18th Street's murals, taquerias, and galleries, the National Museum of Mexican Art, and a brick two-flat housing stock minutes from downtown that keeps drawing buyers priced out of the West Loop..
$200Ks condos to $800K multi-unitsBridgeport
South Side · old neighborhood, new energyBridgeport is the South Side's most quietly transformed neighborhood: the historic home of Chicago mayors and the White Sox, now layered with art spaces like the Zhou B Art Center, a growing restaurant scene on Halsted and Morgan, and housing prices that make North Side buyers do a double take..
$200Ks cottages to $700K new construction