Highwood Holidays

Photo by Tara Jabbari
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Top Flight + Hotel Deals in Highwood

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Hotel Riu Plaza Chicago
Trump International Hotel & Tower Chicago
The Allegro Royal Sonesta Hotel Chicago Loop
Sable at Navy Pier Chicago, Curio Collection by Hilton

Top hotels in Highwood

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 €181 per night from 29 Aug to 30 Aug
€181
29 Aug - 30 Aug
includes taxes & fees
8/10 Very Good! (2,081 reviews)
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Reviewed on 8 Aug 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 €120 per night from 1 Sept to 2 Sept
€120
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (2,370 reviews)
Very nice stay
"The hotel was clean and quiet. Very nice breakfast with eggs, potatoes, bacon, sausage, fruits, and breads. The cleaning staff was very friendly and did a great job."

Reviewed on 6 Aug 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 €132 per night from 25 Aug to 26 Aug
€132
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (1,819 reviews)
"Everything was awesome except the airplanes flying over the hotel, kept waking me up…I will bring earplugs next time :)"

Reviewed on 7 Aug 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.

Popular places to visit

What to do in Highwood

Frequently asked questions

How much does a Highwood holiday package cost?
You'll find cheap prices from €706 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.

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