Winnetka Holidays from £1,424
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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.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was £1,820, price is now £1,424 per person
£1,424
per person
20 Jun - 25 Jun
found 10 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,361 reviews)
This is our favorite hotel in chicago. Great location and staff. Rooms very comfortable.
Reviewed on 11 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £2,531, price is now £1,804 per person
£1,804
per person
14 Jun - 21 Jun
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on 8 May 2026
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was £1,959, price is now £1,506 per person
£1,506
per person
14 Jun - 21 Jun
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Breakfast menu was good, staff at the lounge was good. Checking in was not so good, they wanted to charge me $25 to check in 15 minutes before the time. I think it would be better to say the room is not ready yet the saying your room is ready but is not 2 and if you want it now it will be an extra $25. That I think is ridiculous, which took away from my experience.
Reviewed on 11 May 2026
L7 Chicago by LOTTE
Downtown Chicago
Price was £2,162, price is now £1,705 per person
£1,705
per person
14 Jun - 21 Jun
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (3,985 reviews)
We celebrated my husband's birthday and Laura (or Lauren) was amazing! Super pleasant check in experience, we got aa beautiful room with a magnificent vibes of the Chicago River. We had a dinner at the Korean restaurant on premises, absolutely delicious and interesting. Definitely would recommend this hotel as a romantic getaway, amazing location too.
Reviewed on 12 May 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was £2,922, price is now £2,353 per person
£2,353
per person
14 Jun - 21 Jun
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
I loved staying here!! Very upscale. Staff was so nice. I can’t wait to go back.
Reviewed on 4 May 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
The price is £117 per night from 26 May to 27 May
£117
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.
Reviewed on 12 May 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £151 per night from 25 May to 26 May
£151
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,122 reviews)
Stay was very good, everything was excellent , staff was perfect. BUT at about 1:30 am someone in one of the room near us were fighting ,yelling vey loud, it kept on for quite a while . I worried that someone may have gotten hurt . On phone next to bed I dialed zero was unable to call anyone because ...
Reviewed on 12 May 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 25 May to 26 May
£131
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,302 reviews)
Staff was helpful and friendly. The rooms were clean and spacious!
Reviewed on 12 May 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
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4/5(127 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(147 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Winnetka
Skydeck - Willis Tower Admission
£32
per adult
96% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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- Advocate Illinois Masonic Medical Center
- Allstate Arena
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- Visit Deerfield
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- Visit Evanston
- Gallery Park
- Garfield Park Conservatory
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- Visit North Suburbs
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- 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.
