Highwood Holidays

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Top hotels in Highwood

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is €153 per night from 19 May to 20 May
€153
includes taxes & fees
19 May - 20 May
8.6/10 Excellent! (1,510 reviews)
"Nice"

Reviewed on 24 Apr 2025

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare
Marriott Chicago O'Hare
3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €174 per night from 25 May to 26 May
€174
includes taxes & fees
25 May - 26 May
8.4/10 Very Good! (1,019 reviews)
"Nice property. Clean."

Reviewed on 25 Apr 2025

Marriott Chicago O'Hare
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 €222 per night from 23 May to 24 May
€222
includes taxes & fees
23 May - 24 May
8/10 Very Good! (2,040 reviews)
"We liked the covenince of the hotel, as we got in late off the plane. We didn't like the fact that they allow Housekeeping to knock on the doors at 730am, that is ridiculous when check out is noon, then she knocked on the door again at 11am."

Reviewed on 25 Apr 2025

Hilton Chicago O'Hare Airport
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 holiday 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 holiday 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 holiday packages and you could land some great off-season deals.
How many days is enough for Highwood?
With a well-organised 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 holiday 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 holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking hotels and flights separately. Better still, you can personalise 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 holiday 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, favourite 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 holiday. 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 holiday package that brings all your bookings together.

Popular places to visit

What to do in Highwood

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.