Highwood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Victoria Resort and Bed & Breakfast
North Side
CA $1,785
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (154 reviews)
This is a lovely place to stay with great amenities and special touches. The breakfast was amazing! Highly recommend this gem just 2 blocks from the beach and easy bike ride to downtown. The owner is onsite and very friendly.
Reviewed on Oct 10, 2026
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
CA $1,337
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,491 reviews)
The room was very nice. The kitchen had dish towels and soap for the dishwasher. Loved the full size refrigerator too.
Reviewed on Oct 19, 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 $277
CA $326 total
Oct 31 - Nov 1
includes taxes & fees
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
CA $253
CA $296 total
Oct 31 - Nov 1
includes taxes & fees
8.6/10 Excellent! (1,446 reviews)
"N"
Reviewed on Oct 19, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
CA $227
CA $258 total
Oct 23 - Oct 24
includes taxes & fees
9/10 Wonderful! (3,271 reviews)
"The front desk lady was very helpful checking in and offer the program for an upgrade and free parking for joining!"
Reviewed on Oct 20, 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
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Highwood vacation package cost?
Offering great value package deals from CA $847 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.
