Title: Crestwood Holidays 2026 from £670 | Expedia.co.uk [Crestwood Travel Guide](https://expedia.co.uk/Crestwood.dx6960)[Hotels in Crestwood](https://expedia.co.uk/Crestwood-Hotels.d6960.Travel-Guide-Hotels)[Holiday Rentals in Crestwood](https://expedia.co.uk/Crestwood-Holiday-Rentals.d6960.Travel-Guide-HolidayRentals)[Crestwood Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Crestwood.d6960.Car-Hire-Guide) ![](https://images.trvl-media.com/place/6960/240c7639-252c-425c-9300-8c5e47f6e396.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Crestwood Holidays from £670 ## 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 Crestwood Holiday With plenty of highlights as well as hidden gems, this city is best explored with a Crestwood holiday package. Book a hotel in Hyde Park, which is good for history, nature and culture. A trip to Crestwood is a superb opportunity to do some sightseeing. Be sure to stop by well-known attractions like [Chicago Ridge Shopping Mall](https://www.expedia.co.uk/Chicago-Ridge-Shopping-Mall-Chicago.d6143658.Attraction), [Trinity Christian College](https://www.expedia.co.uk/Trinity-Christian-College-Chicago.d6143660.Attraction) and [Orland Square](https://www.expedia.co.uk/Orland-Square-Chicago.d553248635976375725.Attraction). Whatever your travel plans or budget, organising your ultimate tailored Crestwood holiday is a piece of cake with Expedia. ## Top Crestwood 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 £670 per person 5 May - 8 May found 8 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Amenities, staff was ok Reviewed on 25 Feb 2026 ![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 Save 100% on your flight £1,349 per person 1 May - 6 May found 18 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 Jan 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 £989 per person 1 May - 6 May found 18 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Had a great stay!! Kelly at the front desk was so sweet Reviewed on 22 Feb 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago £675 per person 2 Apr - 7 Apr found 1 day ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Room smelled like food but overall very clean, very great service and staff both night and morning shift. Reviewed on 16 Feb 2026 ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile Downtown Chicago £1,016 per person 1 May - 6 May found 18 hours ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (4,159 reviews) Excellent location and quality for the price! Reviewed on 26 Feb 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=PKG_SPRING_PROMO_6960) ## Crestwood Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 11,000 | | Max Temp Winter | \-1.11ºC | | Max Temp Summer | 27ºC | | Top Sights | [Galloping Ghost](https://www.expedia.co.uk/Galloping-Ghost-Chicago.d553248621532658619.Attraction), [Calumet Beach](https://www.expedia.co.uk/Calumet-Beach-Chicago.d553248635983994343.Attraction) and [Midwest Carvers Museum](https://www.expedia.co.uk/Midwest-Carvers-Museum-Chicago.d6187180.Attraction) | ## Top hotels in Crestwood ![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 £78 27 Feb - 28 Feb includes taxes & fees 8/10 Very Good! (9,937 reviews) Shortly after our check in when noticed our room did not have heat called the operator only to be told the hotels boiler was out, had to call a 2nd time because the toilet wouldn't flush finally when the maintenance guy came to fix the toilet he said he could get us a space heater we was so excited ... Reviewed on 26 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6960) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Plaza Chicago 150 East Ontario Street Chicago IL Fully refundableReserve now, pay when you stay £129 1 Mar - 2 Mar includes taxes & fees 9.4/10 Exceptional! (3,415 reviews) To recessed lights in the ceiling near the windows the windows would not shut off. We tried every little light switch in the room eight ways to Sunday and could not get those recessed lights off. The only way to shut them off was to take the card out to stop the electricity in the room. But then ... Reviewed on 26 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=6960) ![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 £89 4 Mar - 5 Mar includes taxes & fees 8.6/10 Excellent! (5,685 reviews) Service was great, and the staff was very kind. Reviewed on 26 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6960) [See all 3,776 properties in Crestwood](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F02%2F2026&endDate=28%2F02%2F2026®ionId=6960) 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 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 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 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 Crestwood ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission £32 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/skydeck-willis-tower-admission.a1342523.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 Crestwood](https://expedia.co.uk/things-to-do/search?rid=6960) ## Explore a world of travel with Expedia \* 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app