Highwood Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
Find the Best Highwood Vacation Packages
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
₩333,358
₩391,330 total
Sep 27 - Sep 28
includes taxes & fees
8.4/10 Very Good! (2,480 reviews)
"loved everything. train is convenient"
Reviewed on Sep 7, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
₩250,382
₩285,384 total
Oct 4 - Oct 5
includes taxes & fees
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
₩253,209
₩297,242 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (1,386 reviews)
"Unfortunately our room had bugs in it. The pool was not clean and the water felt filmy as if it lacked the adequate amount of chlorine. We did not get a good nights rest as the guests were in the hallway until the wee hours of the morning. Unfortunately we will not choose this location for our future ..."
Reviewed on Sep 6, 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.
Frequently asked questions
How much does a Highwood vacation package cost?
You'll find cheap prices 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 can generally find lower rates and greater availability in January, February and November. Explore our cheap Highwood vacation packages and you could land some great off-season deals.
How many days is enough for Highwood?
With a well-organized travel plan, you can easily visit the top Highwood attractions in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider 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.
How to plan a trip to Highwood?
- Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Highwood.
- Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to experiences and flights. Your hotel will probably be the biggest expense during your trip to Highwood.
- Decide how long to go away for: Now that you're more familiar with Highwood, you can figure out the right length of your vacation. Pull together a rough itinerary and allocate enough time for all the things you want to do.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Highwood 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.
