Highwood Holidays from AU$1,834

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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.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was AU$3,921, price is now AU$1,834 per person
AU$1,834
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,617 reviews)
Comfortable room & bathroom. Everything was fine

Reviewed on 19 Aug. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$4,298, price is now AU$1,981 per person
AU$1,981
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location

Reviewed on 20 Aug. 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,238, price is now AU$1,969 per person
AU$1,969
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.

Reviewed on 20 Aug. 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was AU$4,602, price is now AU$2,176 per person
AU$2,176
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on 17 Aug. 2025

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Price was AU$3,936, price is now AU$1,864 per person
AU$1,864
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8/10 Very Good! (8,974 reviews)
Family had a great stay.

Reviewed on 21 Aug. 2025

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

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 AU$260 per night from 5 Sept to 6 Sept
AU$260
5 Sept - 6 Sept
includes taxes & fees
8.4/10 Very Good! (1,127 reviews)
"Room was grear & bed super comfortable"

Reviewed on 18 Aug. 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 AU$326 per night from 12 Sept to 13 Sept
AU$326
12 Sept - 13 Sept
includes taxes & fees
8.2/10 Very Good! (2,097 reviews)
"The room was clean and the bed was comfortable. The staff was courteous and helpful."

Reviewed on 18 Aug. 2025

Hilton Chicago O'Hare Airport
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$247 per night from 26 Aug to 27 Aug
AU$247
26 Aug - 27 Aug
includes taxes & fees
8.6/10 Excellent! (1,852 reviews)
"Something black was all over our car parked in the garage. It had to have fallen from the ceiling. It was tarlike spots. The breakfast buffet was way too expensive for us retirees. Maybe when we win the lottery!"

Reviewed on 18 Aug. 2025

Hyatt Regency O'Hare Chicago
See all 1,278 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

Discover the most popular places to visit in Highwood

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Highwood

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Highwood

Frequently asked questions

How much does a Highwood holiday package cost?
You'll find cheap prices from AU$1,834 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.