Winnetka Holidays from £861

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Your Winnetka Holiday

When a city adventure is calling, answer it with a Winnetka holiday package. With all your travel needs in place before you leave, all you have to do here is focus on making unforgettable memories. Fill your free time with tours of Chicago Botanic Garden, The Glen Club and North Shore Centre for the Performing Arts, some of the attractions you simply have to see during your trip to Winnetka. Browse Expedia's wide range of travel options and begin planning your perfect holiday to Winnetka now.

Top Winnetka Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Hotel Riu Plaza Chicago
Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton
Hotel Saint Clair- Magnificent Mile

Winnetka Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
12,500
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Montrose Beach

Top hotels in Winnetka

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £101 per night from 5 Apr to 6 Apr
£101
5 Apr - 6 Apr
includes taxes & fees
8/10 Very Good! (9,992 reviews)
The bartender was fantastic ! All of the staff was amazing ! The rooms “all season “ system was not great because it was 45 degrees Friday night and 80 on Saturday so the room was freezing Friday night and so hot Sunday !!! Other than that the hotel was historically beautiful!!

Reviewed on 27 Mar 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is £121 per night from 9 Apr to 10 Apr
£121
9 Apr - 10 Apr
includes taxes & fees
9/10 Wonderful! (3,990 reviews)
Close to everything we wanted to do and the lake and beach

Reviewed on 27 Mar 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £129 per night from 5 Apr to 6 Apr
£129
5 Apr - 6 Apr
includes taxes & fees
8.6/10 Excellent! (5,777 reviews)
We ended up with the stomach bug while we were on vacation, but the staff was all so responsive and helpful to us - allowing a later check-out time and bringing us bleach wipes. The texting feature was very helpful!

Reviewed on 26 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

What to do in Winnetka

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.