Pistakee Highlands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Pistakee Highlands Vacation

Reserve a Pistakee Highlands vacation package that has everything you need and no unnecessary extras. Great for fishing, walking and camping, consider staying in the neighborhood of Camp Lake. If your trip to Pistakee Highlands includes a little sightseeing, drop by well-known attractions like Volo Auto Museum, Petersen Park Beach and McCullom Lake. Stop dreaming and start doing. Browse the wide range of options on Expedia today and finally put your Pistakee Highlands vacation plans into action!

Top Holiday Package Deals in Pistakee Highlands

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,207, price is now CA $798 per person
CA $798
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.

Reviewed on Jun 19, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,758, price is now CA $1,194 per person
CA $1,194
per person
Sep 10 - Sep 14
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.

Reviewed on Jun 20, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Usually this is one of the best property but this time they had water pipe burst and elevators werent working because of that. It was very inconvinient for this stay.

Reviewed on Jun 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,982, price is now CA $1,434 per person
CA $1,434
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Close to a ton of great dining options. Nice staff

Reviewed on Jun 20, 2026

Pistakee Highlands Hotel Deals

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Jun 23 to Jun 24
CA $253
CA $319 total
Jun 23 - Jun 24
includes taxes & fees
9.2/10 Wonderful! (1,351 reviews)
"Excellent view of the lake from the balcony. Some parts, recently painted and updated. Comfortable room and beds. Good shower pressure. Clean, some parts dated."

Reviewed on Jun 21, 2026

Harbor Shores on Lake Geneva
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
1700 Nations Dr Gurnee IL
The price is CA $232 per night from Jun 23 to Jun 24
CA $232
CA $264 total
Jun 23 - Jun 24
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"The room was very clean and comfortable. The Indoorwater park was fun for everyone. The lazy river and wave pool were my favorites."

Reviewed on Jun 20, 2026

Great Wolf Lodge Illinois
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Jul 7 to Jul 8
CA $343
CA $438 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (3,292 reviews)
"Our room was great and very clean! The staff was so nice and was great with my toddler. Waterpark was amazing for my little one!"

Reviewed on Jun 20, 2026

Timber Ridge Lodge and Waterpark
See all 942 properties in Pistakee Highlands
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 Pistakee Highlands vacation package cost?
Starting from just CA $798, a package is your gateway to affordable travel. Put together your Pistakee Highlands adventure by selecting from our wide range of hotels, flights and rental cars.
How do I get a cheap travel package to Pistakee Highlands?
Booking a Pistakee Highlands vacation package with Expedia is a great way to save. We have over 550 partner airlines and 1,000,000 hotel options across the globe. With such a huge range to pick from, you'll have no trouble putting together your ideal escape.
Where should I stay in Pistakee Highlands?
There's lots to explore in Pistakee Highlands, so spend your nights close to its best attractions and treat yourself to more time sightseeing. Stades Farm & Market is one spot to add to your to-do list.
How far in advance should I book my Pistakee Highlands vacation?
Search Expedia to compare international airfares as soon as possible. In most cases, you can purchase a seat up to 12 months prior to departure. If you can't find your preferred air carrier, or you've left things to the last minute, fear not. The lowest prices to Pistakee Highlands occasionally appear a few weeks before the date of departure.
What does an Expedia Pistakee Highlands travel package include?
From hotels and airfares to car rentals, Expedia can help you create a Pistakee Highlands package that's ideal for you. Heading off for a while? Look into a flight, rental car and hotel bundle. If you're taking a short break, an airfare and hotel deal could suit you better. Tours and activities can be added once you've made your booking. Our vacation packages make it simple to plan and save.
What should I know before booking a Pistakee Highlands travel package?
You'll enjoy terrific savings when you combine your flights, hotels and rental cars into a package. Plus, booking everything in one place makes trip planning easier. So why waste your money or time? Whether you're organizing a ritzy city getaway or a budget solo adventure, have a look at our vacation packages today.
Can I choose my airline with a Pistakee Highlands Expedia vacation package?
Yes, definitely. Expedia has more than 550 airline partners to pick from around the globe. With such a huge range of choice, finding the perfect carrier to fly you to Pistakee Highlands won't be hard.
If I'm not able to travel, can I cancel my Pistakee Highlands vacation package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Pistakee Highlands vacation package at no cost if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your car rental company, hotel or airline 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.

Discover the most popular places to visit in Pistakee Highlands

Stades Farm & Market

You can browse for the perfect souvenirs at Stades Farm & Market during your visit to McHenry. Wander the riverfront in this family-friendly area.

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