Hillside Holidays from £889

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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, Oakbrook Centre Mall and Yorktown Shopping Centre. 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.
Hotel Riu Plaza Chicago
Level Chicago Fulton Market
Pendry Chicago
LondonHouse Chicago, Curio Collection by Hilton
Trump International Hotel & Tower Chicago

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.

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, 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, 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, located 17.7km away, or catch thrilling games at Allstate Arena, merely 14.5km from Hillside.

Adventure

Experience the thrill of Galloping Ghost, 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: 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: 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: 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.3°F (-4.3°C)Light RainMostly CloudySlightly LowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudyAverageSlightly Low
March38.3°F (3.5°C)Light RainMostly CloudyAverageAverage
April47.8°F (8.8°C)Light RainMostly CloudySlightly HighAverage
May59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
July74.5°F (23.6°C)Light RainMostly SunnySlightly HighAverage
August73.6°F (23.1°C)Light RainMostly SunnyAverageAverage
September67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
October54.5°F (12.5°C)Light RainMostly SunnySlightly LowSlightly High
November41.4°F (5.2°C)Light RainMostly SunnySlightly LowAverage
December31.8°F (-0.1°C)Light RainMostly CloudyAverageSlightly 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, Rosemont Theatre and Parkway Bank Park Entertainment District

Top hotels in Hillside

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £77 per night from 16 Feb to 17 Feb
£77
16 Feb - 17 Feb
includes taxes & fees
8/10 Very Good! (9,876 reviews)
Staff was great, room service was quick and affordable. Room was spotless.

Reviewed on 10 Feb 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £118 per night from 16 Feb to 17 Feb
£118
16 Feb - 17 Feb
includes taxes & fees
9.2/10 Wonderful! (3,335 reviews)
Best location, breakfast is excellent

Reviewed on 13 Feb 2026

Hotel Riu Plaza Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is £169 per night from 7 Mar to 8 Mar
£169
7 Mar - 8 Mar
includes taxes & fees
8.2/10 Very Good! (2,202 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on 9 Feb 2026

Hilton Chicago O'Hare Airport
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.

Popular places to visit

What to do in Hillside

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* 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.