Hillside Holidays from NZ$1,971

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The Latest Hillside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ohio House Motel

Ohio House Motel

2.5 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
1 block from Target, 2 blocks from Walgreens, easy to get rideshare pickup with the parking lot that the hotel has.

Reviewed on 21 Nov. 2024

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8/10 Very Good! (1,129 reviews)
I loved how conveniently located it was, the staff was friendly, room was clean and I felt very safe! Would definitely return!

Reviewed on 20 Nov. 2024

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (2,053 reviews)
Beautiful high tech property. I would recommend to anyone staying in the Chicago area.

Reviewed on 22 Nov. 2024

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
7.8/10 Good! (7,993 reviews)
We had an excellent stay. The staff was very helpful and our room was clean and spacious, and the location of the hotel was nice as the Art Institute of Chicago and Millennium Park are both within walking distance.

Reviewed on 21 Nov. 2024

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (1,429 reviews)
Room was nice. Service was great. We had a little inconvenience with the room cleanness but the front desk employee helped us and move us to another room. Breakfast was good. The room was excellent for my family. Definitely we will stay there again.

Reviewed on 22 Nov. 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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$172 per night from 24 Nov to 25 Nov
NZ$172
includes taxes & fees
24 Nov - 25 Nov
7.8/10 Good! (8,119 reviews)
"It is an old building so We were very pleased with how clean the rooms were. Tub drained slowly but did not affect our shower schedules. Radiator was a little confusing but it didn’t bother is because the weather was beautiful. Will stay again"

Reviewed on 20 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$199 per night from 23 Dec to 24 Dec
NZ$199
includes taxes & fees
23 Dec - 24 Dec
8.6/10 Excellent! (3,544 reviews)
Book with confidence!
"Booked: two bedroom suite Condition: bed was very comfy and linens felt lovely. Bathroom was well appointed. Spotlessly clean. Rooms could use a remodel and a spruce up, BUT it was not offensively outdated and I have NO complaints on the quality of the space. Microwave also functions as a convection ..."

Reviewed on 20 Nov. 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 22 Dec to 23 Dec
NZ$192
includes taxes & fees
22 Dec - 23 Dec
8.4/10 Very Good! (3,262 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

Reviewed on 21 Nov. 2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,570 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$1,971. 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

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
Wrigley Field which includes a city, central business district and a sporting event

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
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

Flyover in Chicago

Flyover in Chicago

NZ$63
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

NZ$74
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

NZ$89
Per adult
94% of travellers recommend
Architecture River Tour
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.