Hillside Holidays

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Hillside Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Beautiful hotel, quiet clean spacious rooms! Breakfast buffett to die for. Close to museums and Metro.

Reviewed on 24 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We had multiple issues with the locks on our door.

Reviewed on 24 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.

Reviewed on 20 Nov,2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Location is very convenient And the hotel, the room and facilities are nice. I would stay again.

Reviewed on 25 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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Top hotels in Hillside

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 S$158 per night from 8 Dec to 9 Dec
S$158
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (8,142 reviews)
"Ice machines! This was an issue here all summer long. I pointed it out to management over the summer but the issue has gone from bad to worse. Supposedly, there are ice machines on even floors. This visit, housekeeping directed me to the machine on the 4th floor as the only working ice machine. I ..."

Reviewed on 22 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 S$153 per night from 25 Dec to 26 Dec
S$153
includes taxes & fees
25 Dec - 26 Dec
8.6/10 Excellent! (3,551 reviews)
"Is very close to everything"

Reviewed on 23 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 S$152 per night from 25 Dec to 26 Dec
S$152
includes taxes & fees
25 Dec - 26 Dec
8.4/10 Very Good! (3,264 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 4,579 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 S$757. 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.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 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 sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Hillside

Flyover in Chicago

Flyover in Chicago

S$51
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$65
Per adult
94% of travellers recommend
Architecture River Tour
Narrated by certified, local docent

Chicago Architecture Center River Cruise aboard Chicago's First Lady

S$73
Per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.