Hillside Vacations from $557

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Your Hillside Vacation

Book a Hillside vacation package that includes everything you need and nothing you don't. Good for nightlife, bars and pubs and cafes, think about staying in the neighborhood of Wicker Park. Fill your itinerary with tours of Brookfield Zoo, Oakbrook Center Mall and Frank Lloyd Wright Historic District, some of the attractions you shouldn't miss during a trip to Hillside. No matter your travel plans or budget, putting together a tailored Hillside vacation is easy with Expedia.

The Latest Hillside Vacation Packages

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
Save 100% on your flight
per person
Jun 15 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) 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 Apr 24, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Amazing. Definitely coming back!

Reviewed on Apr 20, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (650 reviews)
Great customer service

Reviewed on Apr 21, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
The location was great, rooms were cozy, and staff was friendly! Highly recommend!

Reviewed on Apr 25, 2024

Hillside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
8,200
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District

Hillside Hotel Deals

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 $127 per night from Apr 28 to Apr 29
$127
per night
Apr 28 - Apr 29
7.6/10 Good! (6,404 reviews)
"A great older hotel. Very happy with my stay here."

Reviewed on Apr 23, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $139 per night from Apr 28 to Apr 29
$139
per night
Apr 28 - Apr 29
8.6/10 Excellent! (2,686 reviews)
"Wonderful stay in the best part of town"

Reviewed on Apr 24, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $160 per night from Apr 28 to Apr 29
$160
per night
Apr 28 - Apr 29
8.2/10 Very Good! (1,859 reviews)
"A beautiful hotel n vibe I had a wonderful stay! We loved the peek a boo showers!"

Reviewed on Apr 25, 2024

Eurostars Magnificent Mile
See all 4,637 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.

Explore other types of vacation packages

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All Inclusive Vacations

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Frequently asked questions

How much does a Hillside vacation package cost?
Custom make your Hillside vacation package from only $557. Choose from any combination of hotels, flights and rental cars to pull together the getaway you’ve long been dreaming about. Be sure to add on a few experiences or activities!
How do I get a cheap travel package to Hillside?
Creating your own Hillside vacation package with Expedia is a simple way to save. We have over 550 air carriers and 1,000,000 hotel options worldwide. With such an amazing range to select from, you’ll have no trouble pulling together your dream escape.
Where should I stay in Hillside?
Close to the action. Many visitors like to book hotels in the vicinity of top attractions, like Drury Lane Theater, Oak Brook Golf Course and Elmhurst College.
What are the top hotels in Hillside?
Holiday Inn Express & Suites Chicago West - O’Hare Arpt Area and Best Western Plus Chicago Hillside are among the most well-known properties in Hillside. Why not check out the facilities and rates at each and then make up your mind?
How far in advance should I book my Hillside vacation?
While prices do change, we generally suggest booking your vacation as early as possible. Many international airfares become available on Expedia up to a year in advance. If you’re booking last minute, you might still get lucky. Low prices to Hillside sometimes appear just weeks before departure.
What does an Expedia Hillside travel package include?
Expedia has everything you need to organize your Hillside escape, but how your package is structured is entirely up to you. Choose from any combination of hotels, flights and rental cars. After some tours or activities to keep you entertained? Once you’ve made your booking, you can add them too. No matter your budget or style, there’s a package deal to meet your needs.
What should I know before booking a Hillside travel package?
So many places to travel to, so many things to see. With a travel package, you can check more of them off your list. Combine your flights, hotels and rental cars and make big savings.
Can I choose my airline with a Hillside Expedia vacation package?
With a vacation package, you’re in control. Whether you’re eager to fly to Hillside in economy or business class, simply pick from the available airline options. Expedia has access to more than 550 airline partners around the world.
If I'm not able to travel, can I cancel my Hillside vacation package?
Your situation can change in the blink of an eye, so yes. You may be able to cancel or alter your Hillside vacation package at no cost within 24 hours of booking. For older bookings, you can still make changes, but your airline, hotel or car rental company may charge additional fees. Want more information? Check out our Customer Service Portal. We’ll help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Hillside

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 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(1,805 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

4.5/5(4,870 reviews)

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

Navy Pier

What 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

$54
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$75
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Hillside

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.