Highwood Vacations

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    Save up to AED 148 when you book a flight and hotel together*
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Find the Best Highwood Vacation Packages

Highwood Hotel Deals

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is AED 379 per night from Mar 9 to Mar 10
AED 379
AED 432 total
includes taxes & fees
9 Mar - 10 Mar
8.6/10 Excellent! (1,335 reviews)
"Very nice."

Reviewed on 4 March 2025

Hyatt Regency O'Hare Chicago
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 AED 757 per night from Mar 28 to Mar 29
AED 757
AED 889 total
includes taxes & fees
28 Mar - 29 Mar
8/10 Very Good! (2,043 reviews)
"Friendly staff. Nice facilities"

Reviewed on 2 March 2025

Hilton Chicago O'Hare Airport
Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is AED 397 per night from Mar 16 to Mar 17
AED 397
AED 456 total
includes taxes & fees
16 Mar - 17 Mar
8.4/10 Very Good! (1,023 reviews)
Staycation
"Excellent check in and very friendly customer service. Clean room and lots of options for food. Big pool and nice size fitness center."

Reviewed on 2 March 2025

Hyatt Regency Schaumburg Chicago
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 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.

Discover the most popular places to visit in Highwood