Destination guide

Take in the lush beauty of Winnetka

The forests and surrounding scenery provide a peaceful ambiance to your vacation home in Winnetka. Renowned for its shopping, sporting events and restaurants, this city welcomes all visitors. Wrigley Field and John Hancock Center are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Activities and attractions in and around Winnetka

Are you looking for top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Winnetka has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Skydeck Ledge (16.5 mi / 26.5 km)
  • Lincoln Park Zoo (13.9 mi / 22.4 km)
  • Navy Pier (16.2 mi / 26.1 km)
  • Wagner Farm (1.9 mi / 3.1 km)
  • Willowhill Golf Course (3.1 mi / 4.9 km)
  • The Glen Club (3.9 mi / 6.3 km)
Natural features

Exploring the natural features in Winnetka

Whether you're looking for adventure or just want to spend some time taking in the scenery, Winnetka is a great place to get out in nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Millennium Park (16.5 mi / 26.5 km)
  • Lincoln Park (11.9 mi / 19.1 km)
  • Kent Fuller Air Station Prairie (3.3 mi / 5.3 km)
  • Gallery Park (3.7 mi / 5.9 km)
  • Chicago Botanic Garden (4 mi / 6.4 km)
  • Ravinia Park (4.2 mi / 6.8 km)
How to get there

Transportation to and around Winnetka

Fly into Chicago, IL (PWK-Chicago Executive), the closest airport, located 7.6 mi (12.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Chicago, IL (ORD-O'Hare Intl.), which is 11.6 mi (18.6 km) away.

If you prefer train travel, make your way to Winnetka Station or Winnetka Indian Hill Station to see more of the city.

What is the best area to stay when traveling to Winnetka?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winnetka:

  • Chicago Loop: 573 vacation rentals
  • Wrigleyville: 329 vacation rentals
  • Gold Coast: 182 vacation rentals
  • South Loop: 132 vacation rentals
  • Old Town: 201 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Winnetka?

HomeAway offers a large selection of vacation rentals near lovely places in Winnetka. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Winnetka Station: 1,215 vacation rentals
  • Winnetka Indian Hill Station: 1,221 vacation rentals
  • Grant Park: 988 vacation rentals
  • McCormick Place: 1,106 vacation rentals
  • Chicago Water Tower: 1,288 vacation rentals

But there are many other points of interest around Winnetka listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Winnetka?

Yes, of course. HomeAway has 39 Houses in Winnetka. Our other popular types of vacation rentals in Winnetka include:

  • Condos/Apartments: 131 rentals available
  • Townhouses: 7 rentals available
  • Studios: 116 rentals available

Can I find a vacation rental with pool in Winnetka?

Yes, you can select your preferred vacation rental with pool among our 7 vacation rentals with pool available in Winnetka. Please use our search bar to access the selection of vacation rentals available.

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