Highwood Vacations from ¥243,810

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The Latest Highwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston
Level Chicago - River North
Hotel Riu Plaza Chicago
The Allegro Royal Sonesta Hotel Chicago Loop
Arlo Chicago

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 ¥26,482 per night from Sep 5 to Sep 6
¥26,482
¥31,088 total
Sep 5 - Sep 6
includes taxes & fees
8/10 Very Good! (2,096 reviews)
"I just needed a quiet clean room for the night. Grateful"

Reviewed on Aug 7, 2025

Hilton Chicago O'Hare Airport
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 ¥18,172 per night from Sep 1 to Sep 2
¥18,172
¥20,712 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (2,371 reviews)
"Friendly staff."

Reviewed on Aug 6, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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 ¥19,945 per night from Aug 25 to Aug 26
¥19,945
¥22,733 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (1,823 reviews)
"Nice room. The only downside is the noise from the airport. A white noise machine on the bed stand helps to quiet the room"

Reviewed on Aug 6, 2025

Hyatt Regency O'Hare 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.

Discover the most popular places to visit in Highwood

What to do in Highwood

Frequently asked questions

How much does a Highwood vacation package cost?
You'll find cheap prices from ¥243,810 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.