Title: Winthrop Harbor Holidays 2025 from $301 | Expedia.co.uk [Hotels in Winthrop Harbor](https://expedia.co.uk/Winthrop-Harbor-Hotels.d183192.Travel-Guide-Hotels)[Holiday Rentals in Winthrop Harbor](https://expedia.co.uk/Winthrop-Harbor-Holiday-Rentals.d183192.Travel-Guide-HolidayRentals)[Winthrop Harbor Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winthrop-Harbor.d183192.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) # Winthrop Harbor Holidays from £613 ## 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 ## Top Winthrop Harbor Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![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 £613 per person 6 Nov - 9 Nov found 14 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Excellent location, great restaurants nearby. Nice, spacious rooms. Reviewed on 3 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-06/2025-11-09/?FromAirport=LGW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75tPbfxzZDr_2b0Y6EueqZRhhgNnq5_f-bYtCzjfq_Cw-) ![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 £833 per person 6 Nov - 9 Nov found 14 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Clean room. Great staff Reviewed on 2 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-06/2025-11-09/?FromAirport=LGW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75tPbfxzZDr_2b0Y6EueqZRgPucP5QL6DpryvQVlos0zR) ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston £745 per person 6 Nov - 9 Nov found 14 hours ago Return direct flight included London (LGW) to Chicago (ORD) 7.6/10 Good! (1,007 reviews) Two mornings received poor service at breakfast. King bed in room. Could not open cabinet Reviewed on 15 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-06/2025-11-09/?FromAirport=LGW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19722&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75jmcbn87oY11EhIFM3OCvsYSh8IzBcZNUXpYbcaHsFLi) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £707 per person 6 Nov - 9 Nov found 14 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice. Reviewed on 29 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-06/2025-11-09/?FromAirport=LGW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75tPbfxzZDr_2b0Y6EueqZRivUA5vze6NdzyERdZWj_65) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago £627 per person 6 Nov - 9 Nov found 14 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9/10 Wonderful! (2,765 reviews) Everything was perfect! Reviewed on 2 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-06/2025-11-09/?FromAirport=LGW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17288&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75tPbfxzZDr_2b0Y6EueqZRhIPVywClSuzXJ33HyXlxQv) ## Winthrop Harbour Essential Information | Language | English | | --- | --- | | Currency | U.S dollars | | Population | 6,800 | | Max Temp Winter | \\-1.11ºC | | Max Temp Summer | 24ºC | ## Top hotels in Winthrop Harbor ![Motel Sun Inn](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279846/93033a15_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel Sun Inn 301 Sheridan Road, Winthrop Harbor, IL Fully refundableReserve now, pay when you stay £50 5 Oct - 6 Oct includes taxes & fees 6.8/10 (267 reviews) Filled the bill "We were on a 6 day bike ride and Motel Sun Inn was just what we needed: clean, quiet, and comfortable. The front desk lady was very helpful" Reviewed on 21 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=1279846&PinnedHotelID=1279846&HadPinnedHotel=true®ionId=183192) ![LA VILLA MOTEL](https://images.trvl-media.com/lodging/92000000/91900000/91895900/91895868/ff942b49_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### LA VILLA MOTEL 1401 Sheridan Rd, Winthrop Harbor, IL Fully refundable £51 14 Oct - 15 Oct includes taxes & fees 6.6/10 (59 reviews) "Good service" Reviewed on 30 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=14%2F10%2F2025&endDate=15%2F10%2F2025&selected=91895868&PinnedHotelID=91895868&HadPinnedHotel=true®ionId=183192) ![Hotel Indigo Chicago-Vernon Hills by IHG](https://images.trvl-media.com/lodging/1000000/50000/42600/42520/a9a70adc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Indigo Chicago-Vernon Hills by IHG 450 N Milwaukee Ave, Vernon Hills, IL Fully refundable £93 12 Oct - 13 Oct includes taxes & fees 8.2/10 Very Good! (1,039 reviews) Exceeded expectations... "Everything exceeded expectations..." Reviewed on 30 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F10%2F2025&endDate=13%2F10%2F2025&selected=42520&PinnedHotelID=42520&HadPinnedHotel=true®ionId=183192) [See all 614 properties in Winthrop Harbor](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=183192) 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) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes ### Accommodation - [Antioch Hotels](https://www.expedia.co.uk/Antioch-Hotels.d6427.Travel-Guide-Hotels) - [Beach Park Hotels](https://www.expedia.co.uk/Beach-Park-Hotels.d183175.Travel-Guide-Hotels) - [Lake County Hotels](https://www.expedia.co.uk/Destinations-In-Lake-County.d553248635083912192.Hotel-Destinations) - [Fox Lake Hills Hotels](https://www.expedia.co.uk/Fox-Lake-Hills-Lake-Villa-Hotels.0-n553248635975871210-0.Travel-Guide-Filter-Hotels) - [Grayslake Hotels](https://www.expedia.co.uk/Grayslake-Hotels.d6094870.Travel-Guide-Hotels) - [Green Oaks Hotels](https://www.expedia.co.uk/Green-Oaks-Hotels.d553248634983496352.Travel-Guide-Hotels) - [Adults Only Resorts & in Gurnee](https://www.expedia.co.uk/Gurnee-Hotels-Adults-Only-Resorts.0-0-d8240-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in Gurnee](https://www.expedia.co.uk/Gurnee-Hotels-Hotels-With-Indoor-Pools.0-0-d8240-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - 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[B&B in North Chicago](https://www.expedia.co.uk/North-Chicago-Bed-And-Breakfasts.d9157-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [North Chicago Hotels](https://www.expedia.co.uk/North-Chicago-Hotels.d9157.Travel-Guide-Hotels) - [Old Mill Creek Hotels](https://www.expedia.co.uk/Old-Mill-Creek-Hotels.d553248634983540870.Travel-Guide-Hotels) - [Round Lake Beach Hotels](https://www.expedia.co.uk/Round-Lake-Beach-Hotels.d553248635974904741.Travel-Guide-Hotels) - [Round Lake Hotels](https://www.expedia.co.uk/Round-Lake-Hotels.d6216104.Travel-Guide-Hotels) - [Hotels near Six Flags Great America](https://www.expedia.co.uk/Six-Flags-Great-America-Hotels.0-l6023396-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Vernon Hills](https://www.expedia.co.uk/Vernon-Hills-Hotels-Budget-Hotels.0-0-d6371-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Vernon Hills](https://www.expedia.co.uk/Vernon-Hills-Hotels-Luxury-Hotel.0-0-d6371-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Vernon Hills Hotels](https://www.expedia.co.uk/Vernon-Hills-Hotels.d6371.Travel-Guide-Hotels) - 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[Flights from Chicago (ORD) to Waukegan (UGN)](https://www.expedia.co.uk/lp/flights/ord/ugn/chicago-to-waukegan) ### Packages - [Algonquin Holidays](https://www.expedia.co.uk/Algonquin.d601912.Holidays-City-Breaks) - [Allstate Arena](https://www.expedia.co.uk/Allstate-Arena-OHare.d6069163.Attraction) - [Arboretum of South Barrington](https://www.expedia.co.uk/Arboretum-Of-South-Barrington-Chicago.d6175734.Attraction) - [Crystal Lake Holidays](https://www.expedia.co.uk/Crystal-Lake.d7731.Holidays-City-Breaks) - [Gallery Park](https://www.expedia.co.uk/Gallery-Park-Chicago.d6186155.Attraction) - [Glencoe Holidays](https://www.expedia.co.uk/Glencoe.d54977.Holidays-City-Breaks) - [Gold Pyramid House](https://www.expedia.co.uk/Gold-Pyramid-House-Wadsworth.d6246834.Attraction) - [Golf Holidays](https://www.expedia.co.uk/Golf.d6132095.Holidays-City-Breaks) - [Visit Gurnee](https://www.expedia.co.uk/Gurnee.dx8240) - [Heritage Park](https://www.expedia.co.uk/Heritage-Park-Chicago.d6183460.Attraction) - [Home Alone House](https://www.expedia.co.uk/Home-Alone-House-Chicago.d553248635997949865.Attraction) - [Johnsburg Holidays](https://www.expedia.co.uk/Johnsburg.d3000008336.Holidays-City-Breaks) - [Legoland® Discovery Center](https://www.expedia.co.uk/LEGOLAND-Discovery-Center-Chicago.d6169680.Attraction) - [Lake Forest Holidays](https://www.expedia.co.uk/Lake-Forest.d8508.Holidays-City-Breaks) - [Visit Lake Forest](https://www.expedia.co.uk/Lake-Forest.dx8508) - [Lake Villa Holidays](https://www.expedia.co.uk/Lake-Villa.d6216103.Holidays-City-Breaks) - [Visit Lake Villa](https://www.expedia.co.uk/Lake-Villa.dx6216103) - [Lake Zurich Holidays](https://www.expedia.co.uk/Lake-Zurich.d6122910.Holidays-City-Breaks) - [Lincolnshire Holidays](https://www.expedia.co.uk/Lincolnshire.d8425.Holidays-City-Breaks) - [Montrose Beach](https://www.expedia.co.uk/Montrose-Beach-Uptown.d6277595.Attraction) - [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) - [Northwestern University](https://www.expedia.co.uk/Northwestern-University-Chicago.d6034942.Attraction) - [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) - [Schaumburg Holidays](https://www.expedia.co.uk/Schaumburg.d8107.Holidays-City-Breaks) - [Six Flags Great America](https://www.expedia.co.uk/Six-Flags-Great-America-Chicago.d6023396.Attraction) - [Sleepy Hollow Holidays](https://www.expedia.co.uk/Sleepy-Hollow.d3000435324.Holidays-City-Breaks) - [The Catlow Theater](https://www.expedia.co.uk/The-Catlow-Theater-Barrington.d553248621532658589.Attraction) - [The People's Choice Family Fun Center](https://www.expedia.co.uk/The-Peoples-Choice-Family-Fun-Center-Chicago.d553248621532659203.Attraction) - [Visit Vernon Hills](https://www.expedia.co.uk/Vernon-Hills.dx6371) - [Winnetka Holidays](https://www.expedia.co.uk/Winnetka.d175751.Holidays-City-Breaks) - [Woodfield Mall](https://www.expedia.co.uk/Woodfield-Mall-Chicago.d6064089.Attraction) - [Woodstock Square](https://www.expedia.co.uk/Woodstock-Square-Woodstock.d6186941.Attraction) ### Cars - [Alamo Rent A Car Rental Cars in Lake Catherine](https://www.expedia.co.uk/Alamo-Rent-A-Car-Car-Rentals-In-Lake-Catherine.d553248635975848955-c6.Car-Rental-Guide-Suppliers) - [Car hire in Budget Houston Galleria Area, 4825 Richmond Ave](https://www.expedia.co.uk/Budget-at-Houston-Galleria-Area.v6427.Car-Rental-Guide-Location) - [Car hire Grayslake](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Grayslake.d6094870.Car-Hire-Guide) - [Car hire Gurnee](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Gurnee.d8240.Car-Hire-Guide) - [Car hire Libertyville](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Libertyville.d8612.Car-Hire-Guide) - [Car hire near Rosalind Franklin University of Medicine and Science](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Rosalind-Franklin-University-Of-Medicine-And-Science.d6142963.Car-Hire-Guide) - [Car hire Vernon Hills](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Vernon-Hills.d6371.Car-Hire-Guide) - [Car hire in Thrifty Car Rental 3730 Spenard Road](https://www.expedia.co.uk/Thrifty-Car-Rental-at-3730-Spenard-Road-Anchorage-Alaska-USA.v8508.Car-Rental-Guide-Location) ### Holiday Homes - [Antioch Holiday Rentals](https://www.expedia.co.uk/Antioch-Holiday-Rentals.d6427.Travel-Guide-HolidayRentals) - [Lake Forest Holiday Rentals](https://www.expedia.co.uk/Lake-Forest-Holiday-Rentals.d8508.Travel-Guide-HolidayRentals) - [Vernon Hills Holiday Rentals](https://www.expedia.co.uk/Vernon-Hills-Holiday-Rentals.d6371.Travel-Guide-HolidayRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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