Winnetka Holidays
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Top hotels in Winnetka
Congress Plaza Hotel
The bar being open late is nice and the staff are very helpful.
Reviewed on 12 May, 2026
Hotel Riu Plaza Chicago
Very happy with this hotel! Would definitely stay here again. The rooftop bar was super cool!
Reviewed on 12 May, 2026
Hilton Chicago/Magnificent Mile Suites
Very nice hotel in a great location.
Reviewed on 12 May, 2026
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
What to do in Winnetka
Skydeck - Willis Tower Admission
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
