Title: Hillside Holidays 2026 from £1,166 | Expedia.co.uk [Hotels in Hillside](https://expedia.co.uk/Hillside-Hotels.d8353.Travel-Guide-Hotels)[Holiday Rentals in Hillside](https://expedia.co.uk/Hillside-Holiday-Rentals.d8353.Travel-Guide-HolidayRentals)[Flights to Hillside](https://expedia.co.uk/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights)[Hillside Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Hillside.d8353.Car-Hire-Guide) ![](https://images.trvl-media.com/place/8353/de77b2af-26b0-4678-8e9f-d4750da04bfb.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Hillside Holidays from £1,166 ## Book a Hotel + Flight or Car together to unlock savings Photo by Joe Farmer - ## 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 Hillside Holiday An easy way to experience this vibrant city is with a custom-made Hillside holiday package. Base yourself in the neighbourhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our packages are all about you. Any trip to Hillside needs a well-planned itinerary. Fill yours with major attractions such as [Brookfield Zoo](https://www.expedia.co.uk/Brookfield-Zoo-Chicago.d6064025.Attraction), [Oakbrook Centre Mall](https://www.expedia.co.uk/Oakbrook-Center-Mall-Chicago.d6186894.Attraction) and [Yorktown Shopping Centre](https://www.expedia.co.uk/Yorktown-Shopping-Center-Chicago.d6227539.Attraction). Expedia can help you escape the everyday. Tailor your holiday to Hillside to suit your style of travel, whatever that may be. ## Top Hillside 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 £1,166 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on 8 Jan 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 Save 100% on your flight £1,612 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on 24 Jan 2026 ![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 £1,181 per person 1 Apr - 8 Apr found 1 day ago Return direct flight included Belfast (BFS) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything was great just the doors for entering and exiting the building were a hassle to open and push through. Not accessible easily the revolving door was the only way to get in and out and you had to manually push it. It was a heavy door and hard to push with all your stuff. Reviewed on 29 Jan 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 £1,281 per person 3 Mar - 9 Mar found 22 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 £1,222 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on 18 Jan 2026 ### Things to do near Hillside Hillside is perfect for family-friendly, outdoor, and city-themed holidays. Visitors can enjoy various activities, including an arena entertainment facility, shopping centre, and educational attractions. For a memorable experience, consider participating in guided tours and cocktail parties, which offer a chance to explore the local culture and connect with others. Hillside provides a delightful blend of leisure and excitement for all ages. **Shopping** If you're up for a drive, [Stratford Square Mall](https://www.expedia.co.uk/Stratford-Square-Mall-Chicago.d6247353.Attraction), located 19.3km away, offers a vibrant shopping experience with entertainment options. Closer to Hillside, Wolff's Flea Market, 14.5km away, showcases local goods, while the Hawthorne Works Museum, just 12.9km away, features unique items and history. **Recreation** At the [United Center](https://www.expedia.co.uk/United-Center-Near-West-Side.d6064077.Attraction), immerse yourself in the exhilarating atmosphere of live sports events, just 19.3km from Hillside. Alternatively, enjoy family-friendly outdoor fun at [Sea Lion Aquatic Park](https://www.expedia.co.uk/Sea-Lion-Aquatic-Park-Chicago.d6202594.Attraction), located 17.7km away, or catch thrilling games at [Allstate Arena](https://www.expedia.co.uk/Allstate-Arena-OHare.d6069163.Attraction), merely 14.5km from Hillside. **Adventure** Experience the thrill of [Galloping Ghost](https://www.expedia.co.uk/Galloping-Ghost-Chicago.d553248621532658619.Attraction), an arcade adventure zone offering family-friendly fun, located 8.0km from Hillside. For outdoor enthusiasts, the scenic Salt Creek Trail, also 8.0km away, invites you to hike amidst nature. Don’t miss the excitement at Rainbow Falls Waterpark, 16.1km from Hillside, perfect for family entertainment. **Nightlife** Hillside's nightlife offers vibrant city vibes with venues like Kingston Mines and Blues on Halstead, both 22.5km away. Experience romance and live entertainment at these nightclubs, where you can enjoy great music and a lively atmosphere perfect for a memorable evening out. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions near Hillside Hillside, Illinois, offers a delightful mix of family-friendly activities and city-themed adventures. Visitors can explore urban parks, modern colleges, and event venues, all while enjoying a rich cultural experience. For those seeking a beachside retreat, friendly beaches provide a perfect escape, ensuring a memorable vacation for all types of travellers. - **[Drury Lane Theater: ](https://www.expedia.co.uk/Drury-Lane-Theater-Chicago.d6227548.Attraction)** Located three miles from Hillside, Drury Lane Theater offers a vibrant atmosphere perfect for theatre enthusiasts. This venue hosts a variety of performances, from musicals to plays, ensuring a memorable night out with its professional productions and engaging ambience. - **[Morton Arboretum: ](https://www.expedia.co.uk/Morton-Arboretum-Chicago.d6238155.Attraction)** Nine miles away, Morton Arboretum is a stunning outdoor haven that invites families to explore its extensive gardens and scenic trails. Ideal for nature lovers, it provides educational programmes and activities amidst beautiful landscapes, making it a delightful spot for all ages. - **[Wheaton College: ](https://www.expedia.co.uk/Wheaton-College-Chicago.d6091385.Attraction)** Situated ten miles from Hillside, Wheaton College boasts rich history and culture, featuring beautiful architecture and serene grounds. Visitors can appreciate its commitment to education and enjoy the art exhibits, making it a great place to soak in the local culture. ### Best time to go to Hillside The best time to visit Hillside is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 24.3°F (-4.3°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | February | 26.2°F (-3.2°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | March | 38.3°F (3.5°C) | Light Rain | Mostly Cloudy | Average | Average | | April | 47.8°F (8.8°C) | Light Rain | Mostly Cloudy | Slightly High | Average | | May | 59.7°F (15.4°C) | Light Rain | Mostly Sunny | Average | Average | | June | 69.8°F (21.0°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 74.5°F (23.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Average | Average | | September | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | | October | 54.5°F (12.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly High | | November | 41.4°F (5.2°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 31.8°F (-0.1°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | ### Tips to save on your trip to Hillside - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Hillside. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Hillside Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 8,200 | | Max Temp Winter | \-1.11ºC | | Max Temp Summer | 27ºC | | Top Sights | [Brookfield Zoo](https://www.expedia.co.uk/Brookfield-Zoo-Chicago.d6064025.Attraction), [Rosemont Theatre](https://www.expedia.co.uk/Rosemont-Theatre-OHare.d6064061.Attraction) and [Parkway Bank Park Entertainment District](https://www.expedia.co.uk/Parkway-Bank-Park-Entertainment-District-OHare.d553248621561882886.Attraction) | ## Top hotels in Hillside ![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 £82 17 Feb - 18 Feb includes taxes & fees 8/10 Very Good! (9,824 reviews) Good Reviewed on 30 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=8353) ![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 £91 10 Feb - 11 Feb includes taxes & fees 8.4/10 Very Good! (5,610 reviews) Super friendly staff. The included breakfast was super nice with lots of options and the evening reception was also super nice. Room was clean and nice size. Not something in their control as I think 1-2 of the elevators were out of service but the elevators took forever to come and when they did ... Reviewed on 26 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=8353) ![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 £113 10 Feb - 11 Feb includes taxes & fees 9.2/10 Wonderful! (3,253 reviews) Love the place! Great breakfast buffet. The room was clean, service was great, and great Reviewed on 28 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=8353) [See all 5,306 properties in Hillside](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=31%2F01%2F2026&endDate=01%2F02%2F2026®ionId=8353) 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 Hillside ![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 **90%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket £25 per adult **96%** of travellers recommend [](https://expedia.co.uk/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Hillside](https://expedia.co.uk/things-to-do/search?rid=8353) ## Explore a world of travel with Expedia - 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[Sea Lion Aquatic Park ](https://www.expedia.co.uk/Sea-Lion-Aquatic-Park-Chicago.d6202594.Attraction) - [Stone Park Holidays ](https://www.expedia.co.uk/Stone-Park.d6132202.Holidays-City-Breaks) - [Ty Warner Park ](https://www.expedia.co.uk/Ty-Warner-Park-Chicago.d6187272.Attraction) - [United Center ](https://www.expedia.co.uk/United-Center-Near-West-Side.d6064077.Attraction) - [Unity Temple ](https://www.expedia.co.uk/Unity-Temple-Chicago.d6064079.Attraction) - [Villa Park Holidays ](https://www.expedia.co.uk/Villa-Park.d7471.Holidays-City-Breaks) - [Wheaton College ](https://www.expedia.co.uk/Wheaton-College-Chicago.d6091385.Attraction) - [Willowbrook Holidays ](https://www.expedia.co.uk/Willowbrook.d7870.Holidays-City-Breaks) - [Car hire in Budget 5120 East La Palma Ave Ste 102 ](https://www.expedia.co.uk/Budget-at-5120-East-La-Palma-Ave-Ste-102-Anaheim-California-USA.v7836.Car-Rental-Guide-Location) - [Car hire in Budget Meadows Shopping Ctr - 4800 Baseline Rd, Ste D109a ](https://www.expedia.co.uk/Budget-at-Meadows-Shopping-Ctr-4800-Baseline-Rd.v5986.Car-Rental-Guide-Location) - 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[Things to do in Schiller Park ](https://www.expedia.co.uk/Things-To-Do-In-Schiller-Park.d6710.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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