Stately homes line the streets of residential enclaves, sheltered beneath an awning of towering, shady trees.

Welcome to Winnetka

An affluent, iconic lifestyle on the shores of Lake Michigan


Located along the scenic North Shore, Winnetka is one of the greater Chicago area’s most affluent, historic neighborhoods. One of the nation’s highest household incomes has afforded locals access to top-rated schools, both public and private, Lake Michigan beaches, exclusive golfing clubs, fine dining, and swanky boutiques. Stately homes line the streets of residential enclaves, sheltered beneath an awning of towering, shady trees.


Several of Winnetka’s original structures are still standing today. The Schmidt-Burnham Log House, built-in 1837, is the oldest existing home in town and is on the National Register of Historic Places. Original churches, personal residences of famed architects, and the iconic Georgian colonial beauty from “Home Alone” are all located in Winnetka. Today, residents live among history, architectural significance, and modern businesses established to give locals a better life along Chicago’s North Shore.


For more options, check out these nearby neighborhoods:


What to Love

  • An elevated standard of living includes more prestigious schools, amenities, and dining
  • Lakefront lifestyle with ample historic value
  • Conveniently located Metra line provides transportation into central Chicago

Local Lifestyle

Winnetka locals enjoy a high level of comfort in every aspect of life. Parents rest assured knowing their children attend some of the best-performing public and private schools in the state of Illinois. Days out of the office are spent enjoying fine cuisine prepared by some of Chicago’s most talented chefs, shopping for refined additions to their homes and closets, basking in the sunlight on the shores of Lake Michigan, and hanging around one of the community’s exclusive golf clubs. Friendly neighbors seal the deal for families considering a move from the inner cities.


Dining, Entertainment, and Shopping

Modern creations prepared with old-fashioned techniques reign supreme in Winnetka. From plant-based dinners to gourmet French desserts, and one-of-a-kind shopping, there is something for everyone to appreciate.


Frank and Betsy’s Restaurant is the best place to celebrate festive happenings. Luxurious French and Californian cooking techniques are the house specialty, with the locally sourced lamb shank stealing the show. A cozy yet elegant stop on the North Shore since 1984 has also built a loyal following for their delectable dessert menu, the perfect way to top off any special occasion.


Classical French baking can be appreciated at Cafe Fleurette, located inside Winnetka’s Metra station. Uniquely authentic techniques, not often found in the United States, have given a special treat to lucky passengers waiting to catch trains into Chicago. Chocolate croissants, streusel, homemade bread, and other specialty desserts are just a few of their tantalizing creations.


More healthy options are served at Spirit Elephant, North Shore’s first entirely plant-based restaurant and bar. A bright and airy space has curated a globally inspired menu featuring classics from across the globe, such as breakfast tacos, pad thai, cauliflower wings, flatbreads, and crabless cakes, to name a few. Their brunch is an especially big hit, boasting a rotating selection of seasonally-themed cocktails.


One of Winnetka’s better-known shopping destinations is Material Possessions, a home decor shop selling a classy selection of gifts, dinnerware, bar accessories, entertainment essentials, jewelry, and more. A popular wedding registry spot among locals, Material Possessions carries nationally recognized brands L’Objet, Simon Pearce, and Juliska, among others.


Things To Do

Winnetka benefits from a scenic waterfront location along the North Shore of Lake Michigan, allowing for frequent beach days during summer’s warmer months. Maple Street Beach & Park is a great place for swimming, sunbathing, and enjoying days off with friends and family. The Lloyd Park and Stepan Family Boat Launch is the communal launching point for boaters and kayakers setting off into Lake Michigan from the southern shore of Tower Beach. Winnetka’s southernmost park, Centennial Park, is a members-only beach serving as the community’s dedicated shoreline for four-legged friends to wander freely off-leash. A bit more inland, the Winnetka Golf Club is a gorgeous public course featuring private lessons, indoor winter training, adult and children’s programs, and memberships offering reserved tee times.



Winnetka residents are zoned to some of the best schools in the state, with several excellent private school options also located close by. Some of these campuses include:


  • New Trier High School, grades 9-12; one of Illinois’ best high schools, also features one of the state’s best-ranked STEM programs 
  • North Shore Country Day School, junior kindergarten-12th grade; this rigorous college preparatory school was ranked as Niche’s best K-12 school in the state and boasts a 100% success rate in college and university placement
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