Hillside Holidays from NZ$2,785

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The Latest Hillside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
per person
21 Dec - 28 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (998 reviews)
Aloft Hotel in Clark has dinning uptions at walkable distances as well as other areas of need or necesity

Reviewed on 5 Nov. 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
21 Dec - 28 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
The staff were all wonderful and really helpful. It was our first time in Chicago and they were more than wonderful for pointing us in the correct locations on where we needed to go and what to do

Reviewed on 5 Nov. 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
21 Dec - 28 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,559 reviews)
I enjoyed the rooftop view and food

Reviewed on 6 Nov. 2024

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
21 Dec - 28 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (693 reviews)
Everyone was super friendly and helpful

Reviewed on 7 Nov. 2024

21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
21 Dec - 28 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.6/10 Excellent! (1,852 reviews)
Quiet, clean, comfortable and in a good location I mentioned my amenities for a free upgrade and he smiled at me and didn’t give me an upgrade. This was the first time for me so I didn’t know if I should have been more comfortable requesting the upgrade.

Reviewed on 5 Nov. 2024

Hillside Holiday

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
Fully refundableReserve now, pay when you stay
The price is NZ$265 per night from 20 Nov to 21 Nov
NZ$265
includes taxes & fees
20 Nov - 21 Nov
7.8/10 Good! (8,043 reviews)
"Perfect for travelers. Great hotel bar. Location ideal"

Reviewed on 7 Nov. 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 NZ$197 per night from 8 Dec to 9 Dec
NZ$197
includes taxes & fees
8 Dec - 9 Dec
8.6/10 Excellent! (3,516 reviews)
"Staff was so nice"

Reviewed on 5 Nov. 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 NZ$230 per night from 24 Nov to 25 Nov
NZ$230
includes taxes & fees
24 Nov - 25 Nov
8.2/10 Very Good! (3,171 reviews)
"Will definitely stay again and again .."

Reviewed on 7 Nov. 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.

Frequently asked questions

How much does a Hillside holiday package cost?
Custom make your Hillside holiday package from only NZ$2,785. 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 holiday 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 Theatre, 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 holiday?
While prices do change, we generally suggest booking your holiday 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 organise 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 holiday package?
With a holiday 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 holiday package?
Your situation can change in the blink of an eye, so yes. You may be able to cancel or alter your Hillside holiday 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(21 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(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Image for Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

What to do in Hillside

Image for Flyover in Chicago

Flyover in Chicago

NZ$63
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

NZ$73
Per adult
84% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Image for Chicago River Cocktail Cruise

Chicago River Cocktail Cruise

NZ$97
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.