Highwood Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Highwood Vacation Packages

Highwood Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$5,278 per night from Aug 22 to Aug 23
NT$5,278
NT$6,196 total
Aug 22 - Aug 23
includes taxes & fees
8/10 Very Good! (2,084 reviews)
"Convenient location in the airport, quick blue line train access. Nice bar and restaurant, friendly and helpful staff."

Reviewed on 2025/7/27

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is NT$4,230 per night from Aug 3 to Aug 4
NT$4,230
NT$4,821 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,801 reviews)
"The room we reserve had a very bad odor coming out from the toilet pipes and was very bad. Our family did not enjoy the room so we had to close the bathroom doors but still smelling bad"

Reviewed on 2025/7/27

Hyatt Regency O'Hare Chicago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is NT$3,739 per night from Aug 4 to Aug 5
NT$3,739
NT$4,262 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,333 reviews)
"Staff was 20/10. Rooms were a little smelly and property could use some updating but location is great. Would stay again"

Reviewed on 2025/7/26

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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.

Discover the most popular places to visit in Highwood

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.