Highwood Holidays

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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.

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

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 AU$278 per night from 7 July to 8 July
AU$278
7 July - 8 July
includes taxes & fees
8.8/10 Excellent! (2,768 reviews)
"We were there under duress. Our flights had been canceled, our luggage delayed, and it was so late! The staff was amazing. They were quick and responsive. The room was gorgeous!! I set my alarm and slept late, and there were no disturbances. There was a wait for the restaurant to open. The atrium ..."

Reviewed on 3 July 2026

Hyatt Regency O'Hare Chicago
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 AU$438 per night from 6 July to 7 July
AU$438
6 July - 7 July
includes taxes & fees
8.4/10 Very good! (2,318 reviews)
"Only thing I dont like is after a long haul flight I had to pull my luggage through their unbearable deep shaggy carpets. I was pulling 2 large bags through the lobby and to the room because they do not have porters to help you. That was brutal"

Reviewed on 3 July 2026

Hilton Chicago O'Hare Airport
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
1501 Sherman Ave Evanston IL
Fully refundable
The price is AU$254 per night from 7 July to 8 July
AU$254
7 July - 8 July
includes taxes & fees
8.6/10 Excellent! (1,989 reviews)
"Room is clean and friendly staff. Location is perfect for visit Northwestern University. Be aware of paid breakfast and parking."

Reviewed on 4 July 2026

Holiday Inn Chicago North-Evanston by IHG
See all 1,392 properties in Highwood
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Highwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$64
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Highwood

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.

Explore a world of travel with Expedia

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