From downtown Chicago, drive up north for 16 miles on I-94 W or Lake Shore Dr to visit Winnetka. The village is one of the wealthiest places in the nation in terms of household income and the number one wealthiest town in Illinois. Winnetka is also known as the home of the iconic movie house from Home Alone!

From this walk, you will see a lot of cool designs of many houses and mansions surrounded by big trees during winter. At the end of the walk, you will see the house at 671 Lincoln Ave from one of the most iconic holiday, Home Alone. In 2021, the homeowner offered a one-night stay for up to four guests at the McCallister residence through Airbnb for only $25.

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