Hillside Holidays from £894

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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.
The Royal Sonesta Chicago River North
Level Chicago - River North
Sable at Navy Pier Chicago, Curio Collection by Hilton
Hilton Grand Vacations Club Chicago Magnificent Mile
Hilton Orrington / Evanston

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, 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, 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, perfect for sports enthusiasts. Enjoy cultural performances at Rosemont Theatre, ideal for a romantic evening. For a peaceful retreat, visit Veterans Memorial Park, 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: 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: 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: 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.3°F (-4.3°C)Light RainMostlySlightly LowSlightly Low
February26.2°F (-3.2°C)Light RainMostlyAverageSlightly Low
March38.3°F (3.5°C)Light RainMostlyAverageAverage
April47.8°F (8.8°C)Light RainMostlySlightly 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 RainMostlyAverageSlightly 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, Rosemont Theatre and Parkway Bank Park Entertainment District

Top hotels in Hillside

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 3 Sept to 4 Sept
£132
3 Sept - 4 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"

Reviewed on 19 Aug 2025

The Wade
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 £94 per night from 24 Aug to 25 Aug
£94
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £133 per night from 3 Sept to 4 Sept
£133
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,726 reviews)
"Valet parking was very expensive for leaving your car without using it for 2 days."

Reviewed on 20 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
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

Frequently asked questions

Why should I book my Hillside holiday with Expedia?
Expedia has you covered for all aspects of your upcoming Hillside holiday. You'll always get the best deals, but when you bundle your airfares, accommodation and/or car hire into a holiday package, you can save even more. Want to really make the most of your escape? Add a few exciting activities and tours to your package. We offer flexible cancellation policies on almost all bookings, so there's no need to worry if your travel plans change. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Hillside?
Peak season falls in May, June and August and is an exciting time to visit — but be prepared for bigger crowds and longer queues. November, December and January are usually quieter times of the year. With daytime average temperatures of -4ºC, January is the coolest period in Hillside. The warmest time of year is July, when you can experience average temperatures of 23ºC throughout the day. Whatever the weather, you'll discover plenty of things to keep you entertained here.
What is the top hotel for my holiday in Hillside?
Relax in comfort in Hillside by choosing LondonHouse Chicago, Curio Collection by Hilton as your home base and gateway to adventure and fun.
How do I get a cheap holiday to Hillside?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and hire cars — we've got everything you need. Choose the combination that best fits you and see your savings stack up. We know holidays are never one-size-fits-all. That's why Expedia offers over 400 partner airlines and 321,000 properties from all over the world, so you can customise your Hillside holiday your way. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Hillside holiday?
Ensure your holiday in Hillside is one to remember by checking out its well-known attractions. Brookfield Zoo, SeatGeek Stadium, Donald E. Stephens Convention Centre and Allstate Arena are a few of the things to put on your itinerary while you're in the area.
What is the best area to stay in when on holiday in Hillside?
Hillside has lots of interesting places to explore, like Fresh Meadow Golf Club. Book a stay nearby and make sightseeing hassle-free.
Do I need a visa for my Hillside holiday?
Check the latest information on official government websites. Your nationality and whether you're travelling for leisure, study or business will determine if you'll require a visa for Hillside. Make yourself familiar with the application process, including any required documentation, turnaround times and fees. Finalise your application well in advance to allow sufficient time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Hillside holiday?
Do some research into the types of clothing people in Hillside wear, and consider browsing style blogs for some fashion inspiration. You'll want to create a versatile travel wardrobe with pieces that suit your destination and show off your unique sense of style. Be sure to check the local weather forecast so you can pack appropriately. The warmest time of year in Hillside is July, with average daytime temperatures of 23ºC. If you plan to visit in the coolest month of January, the mercury hovers around -4ºC during the day.
What does an Expedia Hillside holiday include?
Flights, hotels and a cool set of wheels for all your road trip adventures. Simply mix and match your favourite bundle and get access to great discounts. Once you've made your booking, add on some tours and activities and watch your savings pile up. When it comes to planning your Hillside trip, you're the boss! Expedia features different types of properties, with the most sought after in Hillside being private holiday homes and hotels. With Expedia, you can expect the flexibility and freedom to tailor your holiday however you want.
Does Expedia offer Book Now, Pay Later Hillside holidays?
Expedia has joined forces with online lender Klarna to make booking your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that works with your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
  • No-deposit holidays: Hitting the "book now" button is easier with this option. With no upfront fee for your escape, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Hillside Expedia holiday?
With a holiday package, you're in charge. Whether you're eager to fly to Hillside in coach or first class, simply select from the available airline options. Expedia has access to more than 400 partner airlines around the world.

* 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.