Hillside Holidays

Things to do near Hillside

Shopping

In Hillside, visit the Hawthorne Works Museum for unique gifts, just 12.9km away. If you're up for a drive, the French Market offers a vibrant atmosphere 16.1km away, while Stratford Square Mall, located 19.3km away, combines shopping with entertainment and family-friendly activities.

Recreation

The United Center, 19.3km from Hillside, immerses you in an exhilarating sports atmosphere. The Rosemont Theatre, 11.3km away, offers a romantic and cultural experience with diverse performances. Meanwhile, Oak Brook Golf Course, just 4.8km from Hillside, invites you to enjoy outdoor sports in a picturesque setting.

Adventure

At Sky High Sports Niles, 19.3km from Hillside, experience an exhilarating arcadeAdventureZone filled with family-friendly activities. For outdoor enthusiasts, the scenic Salt Creek Trail, located 8.0km away, offers delightful hiking opportunities. Enjoy a splash at Rainbow Falls Waterpark, 16.1km distant, perfect for adventure and family fun.

Nightlife

Hillside offers a vibrant nightlife with venues like Kingston Mines and Blues on Halstead, both 22.5km away. Experience the romantic atmosphere, live blues music, and the city's lively vibe, perfect for an unforgettable night out filled with entertainment and great company.

*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 excellent choice for family and outdoor-themed holidays, offering a variety of attractions such as urban parks, modern universities, and event venues. Visitors can immerse themselves in local culture while enjoying a city experience. For those seeking a beachside retreat, Hillside provides friendly beach settings for relaxation and leisure, making it a perfect destination for travellers of all kinds.

  • Parkway Bank Park Entertainment District: Located 11.3km from Hillside, this vibrant precinct offers a family-friendly atmosphere with a variety of outdoor activities. Enjoy concerts, festivals, and dining options, making it a perfect spot for relaxation and entertainment.
  • Frank Lloyd Wright Historic District: Situated 9.7km from Hillside, this district showcases the architectural genius of Frank Lloyd Wright. Immerse yourself in rich culture as you explore stunning homes and learn about the innovative designs that transformed American architecture.
  • Mayslake Peabody Mansion: Just 8.0km away, this historic mansion invites you to experience its elegant architecture and serene grounds. Discover its cultural significance through guided tours and events that highlight its fascinating history.

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.

Top hotels in Hillside

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
HK$900
HK$1,070 total
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,271 reviews)
"Room 406: Clean and quiet."

Reviewed on 20 Aug 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
HK$1,121
HK$1,333 total
23 Aug - 24 Aug
includes taxes & fees
8/10 Very good! (2,059 reviews)
"Nice"

Reviewed on 21 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
HK$1,972
HK$2,315 total
18 Sept - 19 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 5,001 properties in Hillside
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.

What to do in Hillside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

HK$212
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

HK$369
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

HK$193
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Hillside

Frequently asked questions

How much does a Hillside holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Hillside costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Hillside?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Hillside holiday packages and you could get some great off-season discounts.
How many days is enough for Hillside?
Typically, a handful of days is enough to check out the top attractions during your Hillside holiday. But if you'd like to have more time to rest or take day trips, consider extending your itinerary.
How to find the best Hillside package deals?
Landing a cheap Hillside package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Hillside package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Hillside holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Hillside escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Hillside?
If you're considering an impromptu Hillside getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Hillside?
  1. Choose your travel dates: What you'd like to do in Hillside and your favourite season can help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your accommodation will likely be the biggest expense during your trip to Hillside.
  3. Decide how long to go away for: Now that you're more familiar with Hillside, you can figure out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Hillside holiday package.

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.