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Windy City Magazine
Discover Chicagoland and the Businesses That Drive It

Lake Forest & Lake Bluff

Lake Forest and Lake Bluff are the north end of the North Shore, where the estates get bigger and the Metra ride gets longer. Lake Forest was planned in 1857 around a curving, park-like street plan, and Market Square, built in 1916, is often called the first planned shopping center in the country. Lake Forest College sits near the lake, and the bluffs south of downtown hold the estates of Chicago’s old fortunes. Lake Bluff, the smaller neighbor to the north, has a village green, a small downtown and a beach at the foot of a ravine. Both are in Lake County.

Where it is

On the map, Lake Forest runs from Highland Park and Fort Sheridan north to Lake Bluff between the lake and I-94, with a west side that reaches past Route 41 to the tollway; Lake Bluff continues north to Great Lakes Naval Station. Metra’s Union Pacific North line stops at Lake Forest and Lake Bluff, about an hour to Ogilvie, and the Milwaukee District North line has a separate Lake Forest stop on the west side. Sheridan Road, Green Bay Road and Route 41 run north-south, and I-94 has exits at Route 60 and Route 176.

What to know if you’re moving here

This is estate country with a college town’s downtown, and the numbers reflect it.

  • Housing is estates and single-family homes built from the 1860s on, with typical prices of roughly $600,000 to $8 million and up as a broad editorial estimate as of September 2026.
  • Parking is driveways and garages; Market Square has free lots and street parking.
  • Public schools are Lake Forest District 67, Lake Bluff District 65 and Lake Forest High School District 115.
  • Lake County property taxes apply, and Lake Forest has some of the largest lots and strictest zoning on the shore.
  • Two Metra lines serve Lake Forest, but the ride to the Loop is about an hour either way.
  • The drawback is distance from the city, and a social scene built around clubs and the college rather than restaurants and bars.

What to do if you’re visiting

Market Square and the lakefront are the stops, and both are a short walk from the Lake Forest Metra station; downtown Lake Bluff is one stop north.

  • Market Square on Western Avenue, designed by Howard Van Doren Shaw in 1916, is the walkable shopping district with a landmark clock tower, and the Shlifka family’s Kiddles Sports has sold bikes and team gear from 258 Market Square since 1968.
  • Across Western Avenue, Lake Forest Book Store has been an independent bookseller since 1949, and Gerhard’s Elegant European Desserts a few doors down bakes chocolate mousse cake and almond croissants from scratch.
  • Two blocks east on Illinois Road, the 1929 Deer Path Inn is on the National Register of Historic Places and pours pints in the White Hart Pub and afternoon tea in the lounge.
  • Forest Park Beach at the foot of Deerpath is the public beach, with a breakwater and a bluff-top park.
  • In Lake Bluff, Maevery Public House on Scranton Avenue is the sit-down dinner a block from the Metra station, with shrimp and grits and four wines on tap.
  • West of town on Rockland Road, The Silo has baked deep dish pizza inside a barn and silo since 1968 and won the Taste of Chicago People’s Choice award in 1991 and 1992.

Nearby in the directory

Showing 30 of 344 businesses in and around Lake Forest & Lake Bluff. Browse all of Lake Forest or the full directory.