Hillside Holidays from £635

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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£635
per person
20 Nov - 27 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (2,960 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,606
per person
20 Nov - 27 Nov
found 21 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on 27 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,152
per person
13 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The bed was really good. It was so comfortable that I slept like a baby. And the Breakfast was good also. All stuffs are nice , they always greet me with smil. I’ll recommend RIU Plaza Hotel to my friends if they go to Chicago.

Reviewed on 29 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,158
per person
13 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
My sister and I came to Chicago from Baltimore to see the Obama Presidential Center. When I researched hotels to stay at in Chicago I was very impressed with Swissotel ratings. I could’ve made a better choice. We didn’t get to see everything we wanted to see, but when we do come back to Chicago Swissotel is definitely where we’ll be staying. So if you’re planning on coming to Chicago Swissotel is the best choice.

Reviewed on 29 Aug 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£840
per person
20 Nov - 27 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (159 reviews)

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

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£94
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,201 reviews)
"Second time staying here. Love how close is to stores, walkable everywhere."

Reviewed on 29 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
£126
31 Aug - 1 Sept
includes taxes & fees
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
£202
18 Sept - 19 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,974 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.
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Where to go when
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What to do in Hillside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
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

£35
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

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities 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.

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. Flight-inclusive packages are ATOL protected.