Hillside Vacation Packages

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Your Hillside Vacation

An easy way to experience this vibrant city is with a custom-made Hillside vacation package. Base yourself in the neighborhood 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 Center Mall and Yorktown Shopping Center. Expedia can help you escape the everyday. Tailor your vacation to Hillside to suit your style of travel, whatever that may be.

Top Hillside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
per person
Dec. 26 - Jan. 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (MDW)
8.2/10 Very Good! (1,000 reviews)
It was a good stay! Clean and quiet

Reviewed on Nov. 4, 2024

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
per person
Dec. 26 - Jan. 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,000 reviews)
It was near a lit of dining & shopping places. Near the lake which is lovely. The room just seemed a bit run down.

Reviewed on Nov. 5, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jan. 30 - Feb. 4
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
Our experience here was fantastic. Beautiful property - only bad thing is we wanted to go out on the patio at the restaurant but the door was locked and nobody would come to unlock it. We would still come back.

Reviewed on Nov. 8, 2024

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jan. 30 - Feb. 4
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Excellent service, we will be back!

Reviewed on Nov. 2, 2024

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
per person
Dec. 26 - Jan. 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,005 reviews)
This historic hotel is in the perfect location to visit the city and discover the many bars and restaurants on Chicago’s near north side. It has a nice mix of old and new features, paying homage to the famous Pump Room. Stunning reception. Our room had not really been upgraded to modern standard but the bed was super comfortable. Unfortunately the air conditioning was noisy as was the toilet which was continually running. But it was reasonably priced which made up for it’s shortcomings.

Reviewed on Nov. 3, 2024

Ready to book your vacation to Hillside?

 

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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 CA $189 per night from Nov. 10 to Nov. 11
CA $189
CA $222 total
includes taxes & fees
Nov 10 - Nov 11
7.8/10 Good! (8,043 reviews)
"Perfect for travelers. Great hotel bar. Location ideal"

Reviewed on Nov. 7, 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 CA $135 per night from Dec. 9 to Dec. 10
CA $135
CA $159 total
includes taxes & fees
Dec 9 - Dec 10
8.6/10 Excellent! (3,523 reviews)
"It was great"

Reviewed on Nov. 8, 2024

River Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Nov. 24 to Nov. 25
CA $164
CA $192 total
includes taxes & fees
Nov 24 - Nov 25
8.2/10 Very Good! (3,173 reviews)
"Parking to high!"

Reviewed on Nov. 7, 2024

Embassy Suites by Hilton Chicago Downtown River North
See all 4,522 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Hillside vacation package cost?
Custom make your Hillside vacation package from only CA $770. 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 McCormick Place

McCormick Place

4.5/5(141 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 Wrigley Field

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Image for Navy Pier

Navy Pier

4.5/5(459 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 Flyover in Chicago

Flyover in Chicago

CA $52
Per adult
94% of travellers recommend
Flyover in Chicago
Image for Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $61
Per adult
84% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Image for Chicago River Cocktail Cruise

Chicago River Cocktail Cruise

CA $81
Per adult
90% of travellers recommend
Chicago River Cocktail 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.