Winnetka Holidays from £962
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages 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.
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Price was £1,221, price is now £962 per person
£962
per person
1 Sept - 6 Sept
found 14 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.6/10 Excellent! (1,033 reviews)
Great hotel. Checked in and staff were friendly. The star of this hotel are the manager Maya!!! She was amazing to speak to and had a warm presence. There was a breakfast attendant we had on our second day that was also very nice but I cant remember her name. Will definitely stay here again as the hotel is very secure and clean.
Reviewed on 25 Jun 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was £1,804, price is now £1,235 per person
£1,235
per person
1 Sept - 6 Sept
found 14 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Views were amazing on the water with a bonus fireworks show. Thanks Sable!
Reviewed on 26 Jun 2026
Hilton Chicago
Downtown Chicago
Price was £1,352, price is now £999 per person
£999
per person
1 Sept - 6 Sept
found 14 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.6/10 Excellent! (2,860 reviews)
The hotel is in a great location in Chicago. It is a massive big hotel. A bit outdated but room was clean and bed was very comfortable. For some reason it was not cleaned or serviced every day. Overall, had a good stay.
Reviewed on 27 Jun 2026
Level Chicago Fulton Market
Downtown Chicago
Price was £1,941, price is now £1,517 per person
£1,517
per person
15 Aug - 20 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on 25 Jun 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was £1,248, price is now £976 per person
£976
per person
1 Sept - 6 Sept
found 14 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.8/10 Excellent! (2,047 reviews)
It was an ok stay. Room was clean and the hotel was close to the sites/museums we wanted to see.
Reviewed on 26 Jun 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 £123 per night from 29 Jun to 30 Jun
£123
29 Jun - 30 Jun
includes taxes & fees
8/10 Very good! (10,133 reviews)
"The hotel is a bit run down, but my room was very clean. The breakfast was good, although it is not included, and for some reason I thought it was. The receptionist was amazing. She was very kind and allowed me to check in early, which I really appreciated. The location is also excellent. I’m giving ..."
Reviewed on 26 Jun 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is £148 per night from 5 Jul to 6 Jul
£148
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (4,464 reviews)
"Location was great. Everything at the hotel from checkin to chef out was very smooth."
Reviewed on 26 Jun 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £183 per night from 5 Jul to 6 Jul
£183
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (4,547 reviews)
"No hot water in shower and toilet didn’t flush properly."
Reviewed on 27 Jun 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.
Stay near popular Winnetka attractions
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
Explore a world of travel with Expedia
- 5 Star Hotels in North Suburbs
- Chicago Hotels
- Spa Hotels in Deerfield
- Deerfield Hotels
- Cheap Hotels in Evanston
- Gay-Friendly Hotels in Evanston
- Evanston Hotels
- Four Seasons Hotels in Glencoe
- Glencoe Hotels
- Glenview Hotels
- Golf Hotels
- Gay-Friendly Hotels in Highland Park
- Highland Park Hotels
- Hotels near Home Alone House
- Four Seasons Hotels in Kenilworth
- Kenilworth Hotels
- Lincolnwood Hotels
- Morton Grove Hotels
- Niles Hotels
- Gay-Friendly Hotels in North Evanston
- Gay-Friendly Hotels in North Suburbs
- La Quinta Inn & Suites Hotels in North Suburbs
- Luxury Hotels in North Suburbs
- Pet-Friendly Hotels in North Suburbs
- Spa Hotels in North Suburbs
- North Suburbs Hotels
- Cheap Hotels in Northbrook
- Gay-Friendly Hotels in Northbrook
- Hotels with Entertainment in Northbrook
- Luxury Hotels in Northbrook
- Northbrook Hotels
- Holiday Homes in Northbrook
- Northfield Hotels
- Hotels near Northwestern University
- Hotels near Ryan Field
- Beach Resorts & in Skokie
- Cheap Hotels in Skokie
- Hotels with Indoor Pools in Skokie
- Skokie Hotels
- Techny Hotels
- Gay-Friendly Hotels in Wilmette
- Wilmette Hotels
- Advocate Illinois Masonic Medical Center
- Allstate Arena
- Austin Holidays
- Chicago Water Tower
- Chicago Holidays
- Visit Deerfield
- Ernest Hemingway Museum and House
- Visit Evanston
- Gallery Park
- Garfield Park Conservatory
- Glencoe Holidays
- Golf Holidays
- Heritage Park
- Home Alone House
- John Hancock Center
- Lake Forest Holidays
- Lakeview Holidays
- Lincoln Hall
- Lincoln Park Conservatory
- Lincoln Park Zoo
- Lincoln Park Holidays
- Lincolnshire Holidays
- Montrose Beach
- Visit Morton Grove
- Mount Prospect Holidays
- Norridge Holidays
- Visit North Suburbs
- Northwestern University
- Oak Park Holidays
- River Forest Holidays
- Rosalind Franklin University of Medicine and Science
- Rosemont Holidays
- Unity Temple
- Wrigley Field
* 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.
