Living in the Near North and North Shore Chicago Suburbs (Evanston, Wilmette, Winnetka, Lake Forest): A Guide for Newcomers

What are the Near North/North Shore Suburbs Like?

The Vibe
This corridor is wealthy, leafy, academically serious, and deeply tied to Lake Michigan. Architecture ranges from historic Tudors to lakefront estates to walkable town centers with boutique shopping and cute cafes. There's a heavy emphasis on schools, culture, and green space. Evanston feels a bit more urban, liberal, and youthful thanks to Northwestern, while Winnetka and Lake Forest are quieter, polished, and exclusive.


Major Cities/Neighborhoods

  • Evanston – A lively college town (home to Northwestern University) that blends urban walkability with suburban charm.
  • Wilmette – A polished, family-friendly village with top schools, a lovely downtown, and access to beaches and the Metra.
  • Winnetka – One of the most affluent suburbs in the Midwest, full of historic mansions, elite schools, and manicured parks.
  • Lake Forest – A prestigious suburb farther north with stately homes, country clubs, a historic downtown, and forest preserves.

Why It Works

  • Public schools (New Trier, Evanston Township) are nationally ranked.
  • Easy commutes to Chicago via Metra trains and Lake Shore Drive.
  • Beautiful beaches, parks, and lakefront living without the density of city life.
  • Small-town downtowns with bookstores, coffee shops, and farmers' markets.
  • Strong community pride and well-funded civic amenities (libraries, rec centers).

Watch Out For

  • Extremely high home prices and property taxes, especially in Wilmette, Winnetka, and Lake Forest.
  • More traditional or conservative social scenes in the farther north suburbs.
  • Commute times can creep up if you’re farther north of Evanston.
  • Homes can be historic, charming, but expensive to maintain.

Good Fit For

  • Families who want elite public schools and a safe, green environment.
  • Executives commuting to Chicago or working remotely.
  • Academics and professionals connected to Northwestern University.
  • Buyers who want historic homes, tree-lined streets, and beach access.

Things to Do

  • Northwestern University events – Sports, lectures, music, and art exhibitions.
  • Gillson Park (Wilmette) and Evanston beaches – Lakefront swimming, biking, and picnics.
  • Chicago Botanic Garden – One of the largest and most beautiful in the U.S., just inland.
  • Historic Downtown Lake Forest – Boutique shopping and classic Americana.
  • Dining along Central Street, Evanston and Wilmette’s downtown—some of the best suburban food scenes in Illinois.

Housing Snapshot
Type: Historic single-family homes, some condos, and townhomes near downtown Evanston and Wilmette.

Buy:

  • Evanston: $450K–$1.2M+
  • Wilmette: $750K–$1.5M+
  • Winnetka: $1.2M–$3M+
  • Lake Forest: $750K–$2M+

Rent:

  • Evanston apartments: $1,700–$3,500 (depending on size and location).
  • Wilmette, Winnetka, and Lake Forest have limited rental markets, but expect $2,500–$5,000+ for homes.

Commute & Transit
Metra Union Pacific North Line provides direct, reliable train service to downtown Chicago. Driving via Sheridan Road, I-94 (Edens Expressway), or Lake Shore Drive. Evanston has access to the CTA Purple Line, providing a more urban transit option. Commutes range from 25–60 minutes, depending on suburb and time of day.


Is This Area Right for You?
If you want beautiful homes, top-ranked schools, a safe and green lifestyle, and easy access to Lake Michigan and Chicago, this stretch of the North Shore suburbs is hard to beat—if your budget can handle it.

If you want to expand your search to the greater metro, check out the LookyLOO Review of the Chicago Metro.