Highwood Vacations from $361
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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.
The Latest Highwood vacation packages
Price found within the past 48 hours. Click for updated prices.
What to do in Highwood
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$211 nightly
$248 total
Oct 16 - Oct 17
Total with taxes and fees
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
$161 nightly
$189 total
Oct 30 - Oct 31
Total with taxes and fees
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
$144 nightly
$164 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (2,869 reviews)
"Great Location, but Some Issues During Our Stay The location of the Crowne Plaza in Rosemont was excellent and very convenient for getting around the area. The staff were friendly and pleasant, which we appreciated. Unfortunately, the hotel itself could use some TLC. Much of the furniture was worn ..."
Reviewed on Oct 10, 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.
Find the Best Highwood Vacation Packages
Highwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 5,400 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Genesee Theater, Marriott Theatre and North Shore Center for the Performing Arts |
More vacations you might like
Frequently asked questions
How much does a Highwood vacation package cost?
You'll find cheap prices from $361 on Expedia for your Highwood escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Highwood costs.
What are the cheapest months to go to Highwood?
You're likely to find lower prices and greater availability in December, January and February. Check out our cheap Highwood vacation packages and you could get some great off-season discounts.
How many days is enough for Highwood?
With a well-planned itinerary, you can easily visit the top Highwood sights in a handful of days. But if you prefer to venture off the beaten track or go on day tours, think about booking your Highwood vacation for longer.
How to find the best Highwood package deals?
Bagging a cheap Highwood package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Highwood package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Highwood vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights separately. Better still, you can personalize your Highwood escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Highwood?
If you're considering a spur-of-the-moment Highwood getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Highwood vacation packages?
Set off on your ideal getaway to Highwood with help from our Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up travel deals while they last.
Explore a world of travel with Expedia
- Aparthotels in Highland Park
- La Quinta Inn & Suites Hotels in Highland Park
- Luxury in North Suburbs
- 5 Star Hotels in North Suburbs
- Hotels in Deerfield
- Hotels in Lake Forest
- Hilton Hotels in Highland Park
- Privatevacationhomes in Northbrook
- Boutique in Highland Park
- Bedandbreakfast in Highland Park
- Hotels in Lincolnshire
- Hotels in Northbrook
- Hotels in Highland Park
- Cottages in Lake Bluff
- Motels in Wheeling
- Apartments in Northbrook
- 4 Star Hotels in North Suburbs
- Flights from Philadelphia (PHL) to Wheeling (PWK)
- Air India Limited New Delhi (DEL) to Chicago (ORD) flights
- Flights to Northbrook
- Delta Air Lines Atlanta (ATL) to Chicago (ORD) flights
- Flights to Lake Forest
- Flights to North Chicago
- Flights to Mettawa
- Flights to Lincolnshire
- Flights to Wheeling
- Flights from Jackson (MKL) to Wheeling (PWK)
- Rosemont Vacations
- Six Flags Great America
- LEGOLAND Discovery Center
- Where to stay in Chicago
- North Suburbs All Inclusive Vacation Packages
- Wrigleyville Vacations
- Visit Northbrook
- Visit North Suburbs
- Ravinia Pavilion
- Visit Winnetka
- Where to stay in Rosemont
- Where to stay in Deerfield
- North Chicago Vacations
- Oak Park Vacations
- Schaumburg Vacations
- Bensenville Vacations
- Where to stay in Evanston
- Visit Lincolnshire
- North Suburbs All Inclusive Vacation Packages
- Bellwood Vacations
- North Suburbs All Inclusive Vacation Packages
- Visit Gurnee
- Chicago All Inclusive Vacation Packages
- North Suburbs All Inclusive Vacation Packages
- North Suburbs All Inclusive Vacation Packages
- Visit Wilmette
- Chicago Botanic Garden
- Visit Lake Forest
- Chicago All Inclusive Vacation Packages
- North Suburbs All Inclusive Vacation Packages
- Where to stay in North Chicago
- Where to stay in Arlington Heights
- Where to stay in Glenview
- Visit Evanston
- Chicago Vacations
- Gurnee Vacations
- Visit Deerfield
- Where to stay in Niles
- Zion Vacations
- North Suburbs All Inclusive Vacation Packages
- Where to stay in Carol Stream
- Chicago All Inclusive Vacation Packages
- Visit Waukegan
- Car rentals in Highland Park
- Car rentals in Northbrook
- Car rentals in Lincolnshire
- Car rentals in Lake Forest
- Pickup Car Rentals in Northbrook
- Enterprise Rental Cars in Highland Park
- Car rentals in Lake Bluff
- Van Car Rentals in Highland Park
- Minivan Car Rentals in Gurnee
- Car rentals in Deerfield
- Hertz Rental Cars in Highland Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
