Holiday Hills Vacation Packages

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  • Better together

    Save up to CA $4,200 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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Your Holiday Hills Vacation

With a Holiday Hills vacation package, say goodbye to travel planning and hello to trouble-free adventure. Every detail of your getaway has been taken care of before you depart, so you can spend more time experiencing this fantastic city. If sightseeing is on the cards during your trip to Holiday Hills, stop by popular attractions like Volo Auto Museum, McHenry Shores Beach Park and Petersen Park Beach. Your perfect Holiday Hills vacation is a few clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored just for you.

Top Holiday Hills Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $800, price is now CA $585 per person
CA $585
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,305, price is now CA $932 per person
CA $932
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,406, price is now CA $1,017 per person
CA $1,017
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,080, price is now CA $791 per person
CA $791
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
The bathroom in my room was looking worse for wear, broken tiles and caulk missing. However the room itself was clean and staff was sooooo helpful and courteous which made my stay great! I even was out of body wash and the girl at the front desk made sure I got some after house keeping didn’t bring any after an hour and I wanted to shower. Good people working here!

Reviewed on Oct 28, 2026

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was CA $1,079, price is now CA $810 per person
CA $810
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,253 reviews)
would stay there again love the place

Reviewed on Oct 27, 2026

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Holiday Hills Hotel Deals

Motel 6 Rolling Meadows, IL - Chicago Northwest

Motel 6 Rolling Meadows, IL - Chicago Northwest

2 out of 5
1800 Winnetka Cir Rolling Meadows IL
Fully refundableReserve now, pay when you stay
The price is CA $79 per night from Nov 20 to Nov 21
CA $79
CA $91 total
Nov 20 - Nov 21
includes taxes & fees
Motel 6 Rolling Meadows, IL - Chicago Northwest
Country Inn & Suites by Radisson, Schaumburg, IL

Country Inn & Suites by Radisson, Schaumburg, IL

3 out of 5
1401 North Roselle Road Schaumburg IL
Fully refundable
The price is CA $146 per night from Nov 29 to Nov 30
CA $146
CA $168 total
Nov 29 - Nov 30
includes taxes & fees
8.8/10 Excellent! (1,406 reviews)
"Room was clean, staff was friendly."

Reviewed on Oct 27, 2026

Country Inn & Suites by Radisson, Schaumburg, IL
La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

3 out of 5
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Nov 1 to Nov 2
CA $92
CA $103 total
Nov 1 - Nov 2
includes taxes & fees
La Quinta Inn & Suites by Wyndham Chicago Gurnee
See all 744 properties in Holiday Hills
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Holiday Hills vacation package cost?
You can grab a vacation package to this top destination from CA $585 on Expedia. But how much your vacation to Holiday Hills costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Holiday Hills?
January, February and March are great times to search for cheap Holiday Hills vacation packages. Opting to travel in quieter months means you can generally find lower prices on hotels and flights.
How many days is enough for Holiday Hills?
Generally, a handful of days is enough to tick off the main attractions during your Holiday Hills vacation. But if you'd like to have more time to chill out or go on day tours, consider extending your trip.
How to find the best Holiday Hills package deals?
Use Expedia's filters to help you find some terrific Holiday Hills package deals. When you begin 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 trip for midweek, or look for Holiday Hills package deals in the off-peak season. Play around with your travel dates and you may score 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 Holiday Hills vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and stays individually. Better still, you can customize your Holiday Hills trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Holiday Hills?
If you're considering a spur-of-the-moment Holiday Hills trip, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Holiday Hills?

  1. Pick your travel dates: What you plan to do in Holiday Hills and your favourite season can help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to airfares and activities. Your accommodations will likely be the largest expense during your trip to Holiday Hills.
  3. Determine how many days away: Start by making a list of all the activities and attractions you want to get to in Holiday Hills. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Holiday Hills vacation package that brings all your bookings together.

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