Title: Hillside Holidays 2026 from £617 | 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 £642 ## 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. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago £642 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on 8 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 £1,162 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on 14 Dec 2025 ![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 Save 100% on your flight £784 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Great location, clean room and friendly staff! Reviewed on 14 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 Save 100% on your flight £803 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on 4 Dec 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago Save 100% on your flight £1,332 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!! Reviewed on 15 Dec 2025 ### Things to do near Hillside Hillside offers a delightful mix of family-friendly activities, outdoor adventures, and city-themed attractions. Visitors can enjoy educational experiences, arena entertainment, and theatrical performances. For a taste of local culture, consider attending cocktail parties or embarking on guided tours to explore the area’s unique charm. Whether you’re seeking excitement or relaxation, Hillside has something for everyone. **Shopping** The [Fashion Outlets of Chicago](https://www.expedia.co.uk/Fashion-Outlets-Of-Chicago.d553248621561882885.Vacation-Attraction), located 11.3km from Hillside, offers a vibrant shopping experience with entertainment and family-friendly vibes. If you're up for a drive, [Stratford Square Mall](https://www.expedia.co.uk/Stratford-Square-Mall.d6247353.Vacation-Attraction), 19.3km away, also features diverse shopping and entertainment options. Don't miss Wolff's Flea Market, just 14.5km away, for unique finds. **Recreation** Experience the vibrant energy at [United Center](https://www.expedia.co.uk/United-Center.d6064077.Vacation-Attraction), perfect for sports enthusiasts. Enjoy cultural performances at [Rosemont Theatre](https://www.expedia.co.uk/Rosemont-Theatre.d6064061.Vacation-Attraction), ideal for a romantic evening. For a peaceful retreat, visit [Veterans Memorial Park](https://www.expedia.co.uk/Veterans-Memorial-Park.d6187258.Vacation-Attraction), offering serene spaces for relaxation and wellness amid nature. **Adventure** Experience the thrill of retro gaming at Galloping Ghost, an arcade adventure zone 8.0km from Hillside. For nature lovers, the Salt Creek Trail offers scenic hiking trails 8.0km away. Meanwhile, Rainbow Falls Waterpark, located 16.1km from Hillside, promises family-friendly water fun and entertainment. **Nightlife** For a vibrant night out, head to Kingston Mines, a lively nightclub 22.5km from Hillside, where you'll find romance and city vibes. Alternatively, Blues on Halstead, also 22.5km away, offers an energetic atmosphere perfect for enjoying live entertainment and a taste of the local scene. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions near Hillside Hillside, Illinois, is an ideal destination for family and city-themed outdoor holidays. Visitors can explore urban parks, modern colleges, and event venues, making it perfect for those seeking cultural experiences. Additionally, Hillside offers opportunities for a beachside retreat, featuring friendly beaches and a relaxing atmosphere, ensuring a delightful getaway for all types of travellers. - **[Donald E. Stephens Convention Center: ](https://www.expedia.co.uk/Donald-E-Stephens-Convention-Center.d6034944.Vacation-Attraction)** Located 11.3km from Hillside, this venue is perfect for business travellers and event attendees. With its modern facilities and professional atmosphere, it hosts a variety of conferences, exhibitions, and trade shows, making it a hub of activity and networking. - **[Morton Arboretum: ](https://www.expedia.co.uk/Morton-Arboretum.d6238155.Vacation-Attraction)** A delightful 14.5km from Hillside, this expansive arboretum offers a serene escape into nature. Families can enjoy beautiful gardens, interactive exhibits, and scenic trails, perfect for a leisurely stroll or a picnic amidst stunning flora. - **[University of Illinois Chicago: ](https://www.expedia.co.uk/University-Of-Illinois-Chicago.d6064083.Vacation-Attraction)** Situated 20.9km from Hillside, this historic university is steeped in culture. Visitors can explore its impressive architecture, vibrant campus life, and various cultural events, enriching their understanding of local history and education. ### Best time to go to Hillside The best time to visit Hillside is dependant 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 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 | Slightly Low | Slightly Low | | February | 26.2°F (-3.2°C) | Light Rain | Mostly | Average | Slightly Low | | March | 38.3°F (3.5°C) | Light Rain | Mostly | Average | Average | | April | 47.8°F (8.8°C) | Light Rain | Mostly | 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 | 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 to Hillside during the low season (December to February) for more affordable options. - 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 ![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 £71 5 Jan - 6 Jan 2026 includes taxes & fees 8.8/10 Excellent! (3,478 reviews) The rooms are clean and well-maintained, and they’re conveniently located near a variety of shops. Reviewed on 13 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=8353) ![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 £94 11 Jan - 12 Jan 2026 includes taxes & fees 9.2/10 Wonderful! (2,113 reviews) The staff is so friendly and helpful. We now have stayed here twice and enjoy the hotel. Reviewed on 11 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=8353) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel Wacker at Michigan, Chicago 75 E Wacker Dr Chicago IL Fully refundableReserve now, pay when you stay £66 29 Dec - 30 Dec includes taxes & fees 8.6/10 Excellent! (1,965 reviews) The room was very small but clean. Bathroom is nice. Elevators are extremely slow! Staff is friendly Reviewed on 9 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=889753&PinnedHotelID=889753&HadPinnedHotel=true®ionId=8353) [See all 5,234 properties in Hillside](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®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 ![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 Hillside ![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 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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