Hillside Holidays from £929

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Your Hillside Holiday

Reserve a Hillside holiday package and prepare to experience all this lively city has to offer. Consider basing yourself in the neighbourhood of Wicker Park, which is great for nightlife, bars and pubs and cafes. Eager to explore your new surroundings? Brookfield Zoo, Oakbrook Centre Mall and Yorktown Shopping Centre are just three of the top-rated places to visit during a trip to Hillside. Whatever your travel plans or budget, putting together a tailored Hillside holiday is a walk in the park with Expedia.

The Latest Hillside Holiday Deals

Prices and availability subject to change. Additional terms may apply.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on 10 Jan 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The staff are thoughtful and provide the best service. While I was there, I was already planning to come back and stay there again!

Reviewed on 24 Apr 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on 15 Apr 2024

Hotel Arista

Hotel Arista

4.5 out of 5
per person
1 Jun - 5 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Best hotel I’ve stayed at in a while!

Reviewed on 24 Apr 2024

Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
Bedford Park
per person
1 Jun - 5 Jun
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
One of the things I didn't like was I asked for a room with a pull-out couch and a queen bed. I got a queen bed with no pull-out couch and I was told that the rooms were not clean and this was at 5:00 p.m..

Reviewed on 23 Apr 2024

The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Love the excelente service, view and staff that was so helpful!!

Reviewed on 19 Apr 2024

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

Our pick of the best Hillside Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (6,588 reviews)
"A great older hotel. Very happy with my stay here."

Reviewed on 23 Apr 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service and a fitness centre. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,805 reviews)
"Wonderful stay in the best part of town"

Reviewed on 24 Apr 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa and a fitness centre. Our guests praise the helpful staff and the clean rooms in ...
8.2/10 Very Good! (1,861 reviews)
Lukester trip
"Very nice and clean and the staff was on point"

Reviewed on 25 Apr 2024

Eurostars Magnificent Mile
See all 4,649 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Discover the most popular places to visit in Hillside

Image for Wrigley Field

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
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for 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

Unmissable things to do in Hillside

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

£43
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

£59
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Hillside

* 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.