Winnetka Holidays from £861
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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
Downtown Chicago
Price was £980, price is now £861 per person
£861
per person
2 May - 4 May
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on 24 Mar 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,167, price is now £919 per person
£919
per person
2 May - 4 May
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors.
Reviewed on 27 Mar 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,120, price is now £1,004 per person
£1,004
per person
2 May - 4 May
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
If you want to be central to downtown Chicago this is the hotel. I really enjoyed my stay. Great rooftop bar and 2 attached restaurants you can go to if you don't want to travel outside the hotel. However, the hotel pillows are trash. Bring your own pillow if you dont want a stiff neck
Reviewed on 25 Mar 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was £975, price is now £884 per person
£884
per person
2 May - 4 May
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
Front desk people are out of this world, they are here for the customer.
Reviewed on 26 Mar 2026
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
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
Hilton Chicago/Magnificent Mile Suites
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
Embassy Suites by Hilton Chicago Downtown River North
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
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
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Winnetka
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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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. Flight-inclusive packages are ATOL protected.
