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 $1,179, price is now CA $848 per person
CA $848
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was CA $1,511, price is now CA $1,067 per person
CA $1,067
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,453, price is now CA $1,031 per person
CA $1,031
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was CA $1,243, price is now CA $884 per person
CA $884
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,368, price is now CA $976 per person
CA $976
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)

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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 1 to Nov 2
CA $79
CA $91 total
Nov 1 - Nov 2
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 $167 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 $848 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.