Hillside Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    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

Find the Best Hillside Vacation Packages

Hillside Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 710 per night from Aug 6 to Aug 7
SARĀ 710
SARĀ 809 total
6 Aug - 7 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 691 per night from Jul 19 to Jul 20
SARĀ 691
SARĀ 821 total
19 Jul - 20 Jul
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,123 per night from Aug 9 to Aug 10
SARĀ 1,123
SARĀ 1,335 total
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (1,927 reviews)
"Well... when we got there the rooms weren't ready and we had to wait over 4 hours until we finally got our rooms ready at 9 pm. There was no water in my room. And the room AC was very loud and the constant elevator noise while it moved up and down throughout the night... felt like sleeping next to ..."

Reviewed on 18 July 2026

The Wade
See all 4,872 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 vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Hillside costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Hillside?
You can generally find lower rates and better availability in December, January and February. Browse our cheap Hillside vacation packages and you could land some great off-season discounts.
How to find the best Hillside package deals?
Use Expedia's filter tool to find some fabulous Hillside package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Hillside package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Hillside vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Hillside vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Hillside?
Secure amazing discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Hillside break.
How to plan a trip to Hillside?

  1. Choose your travel dates: What you'd like to do in Hillside and your favorite season will help you decide when to travel.
  2. Budget wisely: Besides the price of your stay, you'll need to consider other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Hillside.
  3. Decide how long to go away for: Now that you know more about Hillside, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Hillside vacation package that brings all your bookings together.