Title: Winnetka Holidays 2026 from £777 | 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/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Winnetka Holidays from £777 ## 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 Save 100% on your flight £777 per person 12 Mar - 18 Mar found 1 day ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) The hotel was nice, clean and spacious. I lowered my stars because the staff was not friendly to the point of being rude when we checked in and out or asked for assistance with bags. I did not feel welcomed. It was like I was imposing on the staff. Reviewed on 26 Dec 2025 ![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 Save 100% on your flight £1,070 per person 13 Mar - 18 Mar found 11 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on 21 Dec 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago £1,340 per person 10 Mar - 17 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on 3 Dec 2025 ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago Save 100% on your flight £841 per person 12 Mar - 18 Mar found 1 day ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots. Reviewed on 18 Dec 2025 ![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 £797 per person 12 Mar - 18 Mar found 1 day ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) The room was fantastic, the rest of the hotel (lobby, gym, bar) is spotless. We arranged an engagement photoshoot in the bar via Laura S (events coordinator) and she was unbelievably helpful in ensuring everything was done correctly and in line with hotel procedure. Will be staying again when we revisit Chicago! Reviewed on 26 Dec 2025 ## 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 ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL Fully refundableReserve now, pay when you stay £78 7 Jan - 8 Jan 2026 includes taxes & fees 8.8/10 Excellent! (3,552 reviews) Excellent check in check out. Staff is amazing. We had a small suite. It was perfect. Clean. Location is perfect Reviewed on 23 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=175751) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL Fully refundableReserve now, pay when you stay £133 2 Jan - 3 Jan 2026 includes taxes & fees 8.4/10 Very Good! (2,174 reviews) Clean rooms, extremely friendly staff, onsite Starbucks, Lockwood restaurant was amazing, beautiful gathering area in the lounge. Close to all the Christmas must do’s. Decorated so so beautifully for Christmas! Reviewed on 24 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=02%2F01%2F2026&endDate=03%2F01%2F2026&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=175751) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Silversmith Hotel Chicago Downtown 10 S Wabash Ave Chicago IL Fully refundableReserve now, pay when you stay 9.2/10 Wonderful! (2,155 reviews) Staff was very friendly. Walkable to restaurants and shopping. Really enjoyed the room and the ammenities. Reviewed on 25 Dec 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=09%2F01%2F2026&endDate=10%2F01%2F2026&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=175751) [](https://expedia.co.uk/Hotel-Search?startDate=09%2F01%2F2026&endDate=10%2F01%2F2026&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=175751) [See all 4,620 properties in Winnetka](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®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 ![Magnificent Mile - River North which includes street scenes, signage and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction) ![Wrigley Field featuring a city, a sporting event and city views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 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) ![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 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 ![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) ![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) ![Chicago C3® : Save on admission to your choice of 3 top attractactions](https://mediaim.expedia.com/localexpert/46362450/da44d619-18fc-4969-97e2-f7b8d0da99b5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago C3® by CityPASS® £79 per adult **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.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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