Highwood Holidays from AU$666
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Your Highwood Holiday
Planning your next big travel adventure is easy with a Highwood holiday package. The neighbourhood of Riverwoods, which is good for nature, makes an ideal starting point to discover the treasures of this city. Make your trip to Highwood even more enjoyable by going sightseeing. Chicago Botanic Garden, Lake Forest College and Marriott Theatre are among the most popular attractions worth exploring. No matter your travel plans or budget, organising a tailored Highwood holiday is a piece of cake with Expedia.
The Latest Highwood Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Highwood Holiday
Highwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 5,400 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Genesee Theatre, Marriott Theatre and North Shore Centre for the Performing Arts |
Our pick of the best Highwood Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
AU$256
29 Aug - 30 Aug
includes taxes & fees
9/10 Wonderful! (3,037 reviews)
"We had a quick stay but it was lovely."
Reviewed on 18 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
AU$397
12 Sept - 13 Sept
includes taxes & fees
8.4/10 Very good! (2,421 reviews)
"The bed was hard and the air conditioner was so loud that it kept waking us up throughout the night. Not a good nights sleep at all."
Reviewed on 18 Aug 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
AU$258
23 Aug - 24 Aug
includes taxes & fees
8.6/10 Excellent! (2,950 reviews)
"Wonderful stay, right across from the convention center"
Reviewed on 18 Aug 2026
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
AU$35
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
AU$58
per adult
94% of travellers recommend
Frequently asked questions
How much does a Highwood holiday package cost?
You'll find cheap prices from AU$666 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.
