Title: Winnetka Holidays 2026 from £819 | Expedia.co.uk [Winnetka Travel Guide](https://expedia.co.uk/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.co.uk/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Holiday Rentals in Winnetka](https://expedia.co.uk/Winnetka-Holiday-Rentals.d175751.Travel-Guide-HolidayRentals)[Flights to Winnetka](https://expedia.co.uk/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights)[Winnetka Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winnetka.d175751.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winnetka Holidays from £819 ## 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](https://www.expedia.co.uk/Chicago-Botanic-Garden-Chicago.d6064029.Attraction), [The Glen Club](https://www.expedia.co.uk/The-Glen-Club-Chicago.d6227490.Attraction) and [North Shore Centre for the Performing Arts](https://www.expedia.co.uk/North-Shore-Center-For-The-Performing-Arts-Chicago.d6152652.Attraction), 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 Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £819 per person 19 Mar - 24 Mar found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10 Reviewed on 9 Feb 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £1,063 per person 12 Mar - 16 Mar found 3 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 2026 ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago £1,180 per person 19 Mar - 24 Mar found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Gorgeous property, facilities, and location. Reviewed on 6 Feb 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago £837 per person 19 Mar - 24 Mar found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! Reviewed on 2 Feb 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £886 per person 19 Mar - 24 Mar found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on 31 Jan 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](https://www.expedia.co.uk/Rosemont-Theatre-OHare.d6064061.Attraction), [Parkway Bank Park Entertainment District](https://www.expedia.co.uk/Parkway-Bank-Park-Entertainment-District-OHare.d553248621561882886.Attraction) and [Montrose Beach](https://www.expedia.co.uk/Montrose-Beach-Uptown.d6277595.Attraction) | ## Top hotels in Winnetka ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay £77 11 Feb - 12 Feb includes taxes & fees 8/10 Very Good! (9,848 reviews) Wonderful hotel Reviewed on 4 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=175751) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL Fully refundableReserve now, pay when you stay £176 7 Mar - 8 Mar includes taxes & fees 8.2/10 Very Good! (2,211 reviews) Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay. Reviewed on 2 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=07%2F03%2F2026&endDate=08%2F03%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=175751) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL Fully refundableReserve now, pay when you stay £88 22 Feb - 23 Feb includes taxes & fees 8.4/10 Very Good! (5,643 reviews) Positives- As my friend said as we went to breakfast “the people here are so nice and look happy to work here!” I agree! Eloisa (I hope that is correct-our bartender ) made happy hour on Friday night even happier! She was friendly and knowledgeable, suggesting drinks we hadn’t had before just by ... Reviewed on 8 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=175751) [See all 4,625 properties in Winnetka](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026®ionId=175751) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Popular places to visit ![Wrigley Field featuring a city, a sporting event and city views](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 4.5/5(40 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction) ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue 4.5/5(14 reviews) 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. [](https://expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4/5(125 reviews) A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.co.uk/Navy-Pier-Downtown-Chicago.d6069215.Attraction) ### What to do in Winnetka ![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Navy Pier Centennial Wheel Ticket £18 per adult **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago £28 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour £30 per adult **94%** of travellers recommend [](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) [See all activities in Winnetka](https://expedia.co.uk/things-to-do/search?rid=175751) ## Explore a world of travel with Expedia - 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[Visit Morton Grove ](https://www.expedia.co.uk/Morton-Grove.dx8978) - [Mount Prospect Holidays ](https://www.expedia.co.uk/Mount-Prospect.d8988.Holidays-City-Breaks) - [Norridge Holidays ](https://www.expedia.co.uk/Norridge.d138872.Holidays-City-Breaks) - [Visit North Suburbs ](https://www.expedia.co.uk/North-Suburbs.dx6059336) - [Northwestern University ](https://www.expedia.co.uk/Northwestern-University-Chicago.d6034942.Attraction) - [Oak Park Holidays ](https://www.expedia.co.uk/Oak-Park.d9228.Holidays-City-Breaks) - [River Forest Holidays ](https://www.expedia.co.uk/River-Forest.d5986.Holidays-City-Breaks) - [Rosalind Franklin University of Medicine and Science ](https://www.expedia.co.uk/Rosalind-Franklin-University-Of-Medicine-And-Science-Chicago.d6142963.Attraction) - [Rosemont Holidays ](https://www.expedia.co.uk/Rosemont.d7581.Holidays-City-Breaks) - [Unity Temple ](https://www.expedia.co.uk/Unity-Temple-Chicago.d6064079.Attraction) - [Wrigley Field ](https://www.expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction) - [Car hire Evanston ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Evanston.d8049.Car-Hire-Guide) - [Car hire Glenview ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Glenview.d8006.Car-Hire-Guide) - [Car hire Golf ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Golf.d6132095.Car-Hire-Guide) - [Car hire Lincolnwood ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lincolnwood.d8624.Car-Hire-Guide) - [Car hire near North Suburbs ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-North-Suburbs.d6059336.Car-Hire-Guide) - [Car hire Northbrook ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Northbrook.d9142.Car-Hire-Guide) - [Car hire Skokie ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Skokie.d6903.Car-Hire-Guide) - [Enterprise Rental Cars in Golf ](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Golf.d6132095-c15.Car-Rental-Guide-Suppliers) - [Midway Car Rental Rental Cars in North Suburbs ](https://www.expedia.co.uk/Midway-Car-Rental-Car-Rentals-In-North-Suburbs.d6059336-c27.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in Golf ](https://www.expedia.co.uk/Sixt-Car-Rentals-In-Golf.d6132095-c35.Car-Rental-Guide-Suppliers) - [Evanston Holiday Rentals ](https://www.expedia.co.uk/Evanston-Holiday-Rentals.d8049.Travel-Guide-HolidayRentals) - [Golf Holiday Rentals ](https://www.expedia.co.uk/Golf-Holiday-Rentals.d6132095.Travel-Guide-HolidayRentals) - [Northbrook Holiday Rentals ](https://www.expedia.co.uk/Northbrook-Holiday-Rentals.d9142.Travel-Guide-HolidayRentals) - [Northfield Holiday Rentals ](https://www.expedia.co.uk/Northfield-Holiday-Rentals.d6132153.Travel-Guide-HolidayRentals) - [Wilmette Holiday Rentals ](https://www.expedia.co.uk/Wilmette-Holiday-Rentals.d54976.Travel-Guide-HolidayRentals) - [Things to do in North Suburbs ](https://www.expedia.co.uk/Things-To-Do-In-North-Suburbs.d6059336.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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