Highwood Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Highwood
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
€1,257
per person
26 Oct - 30 Oct
found 15 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The hotel was so amazing for us. Staff was accommodating and helped us immensely. The restaurant for breakfast and the roof top wil keep you coming back. We will try to stay there as much as we can while in Chicago.. Lester and Luis at the restaurants need a bonus. They kept the breakfast crowd well organized.
Reviewed on 4 Sept 2026
Arlo Chicago
Downtown Chicago
€874
per person
18 Nov - 22 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,321 reviews)
Everything that my wife and I experienced at this hotel was excellent. The staff , location , food ,drinks made our stay memorable. We highly recommend and will definitely be back.!!
Reviewed on 5 Sept 2026
Top hotels in Highwood
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
€254
27 Sept - 28 Sept
includes taxes & fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
€176
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (3,114 reviews)
"Had a quiet and productive weekend. Will definitely stay here again. Thanks"
Reviewed on 4 Sept 2026
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
€190
27 Sept - 28 Sept
includes taxes & fees
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.
What to do in Highwood
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
90% of travellers recommend
Frequently asked questions
How much does a Highwood holiday package cost?
You'll find cheap prices from €708 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?
- 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.
- 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.
- 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.
- 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.
