Hillside Holidays from £1,244

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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Plenty of options to eat at Navy Pier and parking was very close using the East garage. Hotel used texting feature which was great for any questions or assistance. Great view of the water from our room. Great location to access boat cruises and fireworks

Reviewed on 18 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Beautiful and upscale property

Reviewed on 17 Jul 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (3,033 reviews)
Staff was friendly and attentive!

Reviewed on 17 Jul 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Despite some communication difficulties upon booking as to whether an accessible room would be available, we ended up in a spacious, super accessible beautiful room. The only thing that was inconvenient was how far the accessible rooms were from elevator. I understand that the size of the room probably accounts for the reason why but as a disabled person, the distance was difficult. They have a great bar and restaurant in the lobby, and a cute movie on the roof event on weekends. The only thing that could possibly improve it is a pool. The neighborhood is very lively and diverse with plenty of nightlife within walking distance.

Reviewed on 15 Jul 2025

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 £118 per night from 18 Aug to 19 Aug
£118
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (8,856 reviews)
"I loved everything about my stay at the congress plaza. Were the rooms updated no. But it had it charm. I am in love with the designs of the 1920. The staff were extremely accommodating. They did not even charge me for late check out. I will be staying here again."

Reviewed on 16 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £265 per night from 10 Aug to 11 Aug
£265
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,045 reviews)
"Very close to popular places."

Reviewed on 16 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £126 per night from 17 Aug to 18 Aug
£126
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,454 reviews)
Connecting room
"Hotel property was amazing. Room was very clean and staff was friendly. Location was perfect. I was shocked to find that my room was connected to another room by just a deadbolt and door jam. That made me feel very uncomfortable and could barely sleep. By the time I realized that, I felt that it ..."

Reviewed on 16 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,970 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

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.

Michigan Avenue

What to do in Hillside

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
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.

* 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.