Highwood Vacation Packages
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Your Highwood Vacation
Book a custom vacation package to Highwood and get ready to experience this incredible city how you like. Consider staying in the neighborhood of Riverwoods, which is good for nature and tons more. A trip to Highwood is an excellent opportunity to take in the sights. Be sure to look around renowned attractions like Chicago Botanic Garden, Lake Forest College and Marriott Theatre. No matter your travel plans or the size of your budget, putting together a tailored Highwood vacation is a breeze with Expedia.
Top Highwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $704
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,698
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
Freehand Chicago
Downtown Chicago
CA $2,050
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (3,367 reviews)
Pros - this hotel is conveniently located and its less expensive than some others in the area.
Cons - the first room I was given had water damage in the ceiling and did not smell good. I also checked the AC unit and the filter was completely clogged with dust, this type of washable filter is supposed to be cleaned every month and it looks like it has at least 9+ months of dust on it. I complained about the water damage and they moved me to another room. The next room didn't have soap or shampoo in the bathroom for some reason, and I checked the air filter in this room also and it clearly hasn't been cleaned in forever. In addition to cleaning the air filters, this type of AC unit is supposed to be professionally cleaned once per year. This one has clearly not been cleaned in years.
If you want a well maintained hotel, try somewhere else.
Reviewed on Sep 2, 2026
Ready to book your vacation to Highwood?
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $367
CA $431 total
Sep 27 - Sep 28
includes taxes & fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
CA $248
CA $282 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (3,105 reviews)
"Clean ,relaxing and helpful staff . Will be returning"
Reviewed on Sep 3, 2026
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
CA $261
CA $307 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (1,376 reviews)
"Staff friendly shuttle service was great"
Reviewed on Sep 2, 2026
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.
What to do in Highwood
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Frequently asked questions
How much does a Highwood vacation package cost?
Offering great value package deals from CA $704 on Expedia, you'll be pleasantly surprised at how much a vacation to Highwood costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Highwood?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Highwood vacation packages and you could land some great off-season deals.
How many days is enough for Highwood?
Allow around 2 days for your Highwood vacation if you're hoping to immerse yourself in everything that makes this place unique. Wander around key neighbourhoods, including Riverwoods and Bannockburn. Then check out top sights such as Marriott Theatre and Highland Park Country Club. With a well-planned itinerary, you'll be kept busy with room for some rest time too. Want to travel beyond Highwood? Consider an excursion or two.
How to find the best Highwood package deals?
Bagging a cheap Highwood package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most economical Highwood package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Highwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still have the freedom to create a personalized Highwood vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Highwood?
Secure incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Highwood vacation.
How to plan a trip to Highwood?
- Choose when to go: Check your diary and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit Highwood.
- Budget wisely: On top of the price of your stay, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Highwood.
- Decide your trip length: Think about how long you want to spend discovering Highwood. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Highwood vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
