Winnetka Vacations

A popular destination within the dynamic city of Chicago, Winnetka has a great deal to offer tourists. The city center of Chicago is just 17 miles (27 kilometers) away, while O'Hare International Airport is located 13 miles (21 kilometers) to the northwest of Winnetka.

While you are in Winnetka, why not spend a few hours sightseeing in nearby areas, like Wilmette, Glencoe and Gross Point.

Chicago’s city center is full of fascinating sights, like Willis Tower and McCormick Place. If you have enough time, it’s worth investigating Millennium Park and Hancock Tower before returning to Winnetka.

Sports lovers vacationing in Winnetka should get tickets for nearby Ryan Field, Evanston to see the Northwestern Wildcats football in action. On game days the area around the stadium becomes a sea of purple and white, as college football fans join together to cheer on their beloved team.

When it’s time to put your feet up after a busy day discovering the many charms of Winnetka, check in to one of the area's range of short and long stay accommodation options. If you're looking for great service and a comfortable bed, it’s hard to go past the Hampton Inn & Suites Chicago-North Shore/Skokie, the Renaissance Chicago North Shore Hotel, Northbrook, and the Extended Stay America Chicago - Skokie.

Read less

Top Hotel Deals

See all Winnetka hotels
1.0 out of 5 stars
1.5 out of 5 stars
2.0 out of 5 stars
2.5 out of 5 stars
3.0 out of 5 stars
3.5 out of 5 stars
4.0 out of 5 stars
4.5 out of 5 stars
5.0 out of 5 stars
Most popular package deals found by our travelers
Most popular package deals found by [originCity] travelers

Top Flight + Hotel Deals

See all Winnetka packages

Top Deals on Flights

See all Winnetka flights

Book a Vacation to Winnetka