Hillside Holidays from £876

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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.

The Latest Hillside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago

4 out of 5
per person
18 Sept - 23 Sept
found 13 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Parking lot under construction messing amd challenging to get to main entrance. Front desk staff pleasant and very helpful. Inner building lacked clear instruction to locate pool, sauna steam room. Rooms were excellent bed super comfy. Disappointed in breakfast i miss understood i thought set up was brunch. Overall ok nearby Oak Brook mall and fine eatry. Review other spa like lodges before locking into this location. Happy travels....

Reviewed on 3 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Staff was very friendly and helpful. We had a great stay in every way possible!

Reviewed on 30 Jun 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair.

Reviewed on 1 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Always love our stay at The Peninsula!

Reviewed on 29 Jun 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
I had such a lovely staycation, and I recommend a stay here to everyone I know.

Reviewed on 26 Jun 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,549 reviews)
The staff was so kind. The room was amazing. Our new go-to for Chicago.

Reviewed on 2 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

Our pick of the best Hillside Hotel Deals

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy a fitness centre, valet parking (surcharge) and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,361 reviews)
"This is a great hotel. Located on a street just east of the John Hancock Center, most of the hotel rooms have bedrooms, microwaves and refrigerators as well as couches. It is comfortable, close to soundproof and the restaurant downstairs has long hours and great food including gourmet coffee. A real ..."

Reviewed on 1 Jul 2025

Hilton Chicago/Magnificent Mile Suites
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,962 reviews)
"Really beautiful deco pool, very centrally located, otherwise quite basic amenities but no complaints. Parking is $78 a night."

Reviewed on 2 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
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 Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (8,920 reviews)
Great value
"The room had a strange smell; not bad just odd. Great view but lots of light in the AM. Great walking distance to lots of cool stuff!"

Reviewed on 30 Jun 2025

Congress Plaza Hotel
See all 4,940 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

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

Unmissable things to do in Hillside

River tour boat in Chicago

Architecture River Tour

£36
per adult
94% 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
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.