Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Joe Farmer

  • Plan, book, travel with confidence

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    Better together

    Save up to Rp173.195 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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 Rp3.031.232 per night from 14 Sept to 15 Sept
Rp3.031.232
Rp3.558.363 total
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,984 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"

Reviewed on 14 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp2.794.341 per night from 2 Sept to 3 Sept
Rp2.794.341
Rp3.683.153 total
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,852 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on 13 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp2.314.920 per night from 4 Sept to 5 Sept
Rp2.314.920
Rp2.717.311 total
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,072 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

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

Wrigley Field
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Hillside

River tour boat in Chicago

Architecture River Tour

Rp684.530
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

Rp743.085
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

Rp668.777
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Hillside

Frequently asked questions

How much does a Hillside holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Hillside costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Hillside?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Hillside holiday packages and you could get some great off-season discounts.
How many days is enough for Hillside?
Typically, a handful of days is enough to check out the top attractions during your Hillside holiday. But if you'd like to have more time to rest or take day trips, consider extending your itinerary.
How to find the best Hillside package deals?
Landing a cheap Hillside package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Hillside package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Hillside holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Hillside escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Hillside?
If you're considering an impromptu Hillside getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Hillside?

  1. Choose your travel dates: What you'd like to do in Hillside and your favourite season can help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your accommodation will likely be the biggest expense during your trip to Hillside.
  3. Decide how long to go away for: Now that you're more familiar with Hillside, you can figure out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Hillside holiday package.

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