Hillside Vacations from $377

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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

Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
7.8/10 Good! (2,530 reviews)
Friendly staff but you can hear the traffic through the road

Reviewed on May 19, 2024

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
Aug 1 - Aug 4
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,622 reviews)
Nice room, nice pool and gym. They weren’t able to give us early checkin, which I understand, and they were able to give us early pool access. But they also weren’t able to give us late checkout, which I have never experienced at a hotel. Not even 30 minutes.

Reviewed on May 19, 2024

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The Ambassador is one of my favorite places to stay while visiting Chicago. Though, born and raised from Chicago, the ambassador is placed in the rich and lush area in the Gold coast neighborhood in Chicago. There's plenty to do and various lovely restaurants, luxury clothing shops, beautiful architecture and transportation nearby. The hotel itself is legendary for having renowned guests in its history. Its comfortable, lively, accessible, and staff is really keen to help and serve numerous guests whom stay. I highly recommend for people to book and stay. Plan to comeback and stay again :)

Reviewed on May 20, 2024

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 12 - Jul 14
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (2,193 reviews)
Rooms are outdated - sheets had a tear in it and chair “leather” was rubbing off. Also no shampoo or shower gel in those containers in the shower - and it’s too late to find that out when you are already in the shower. Disappointed for the price!!

Reviewed on May 20, 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
The price is $167 per night from May 27 to May 28
$167
$196 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,780 reviews)
"Room was renovated, and very nice and clean. For an old hotel, this was a very nice experience!"

Reviewed on May 20, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $171 per night from May 27 to May 28
$171
$201 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (2,885 reviews)
"Staff at the front desk are really helpful and friendly"

Reviewed on May 19, 2024

River Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $125 per night from May 27 to May 28
$125
$162 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,595 reviews)
"Very cozy"

Reviewed on May 20, 2024

Warwick Allerton - Chicago
See all 4,654 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

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Hillside vacation package cost?
Custom make your Hillside vacation package from only $377. 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 Six Flags Great America

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Hillside

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$229
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
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
See all activities in Hillside

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