Highwood Holidays from NZ$1,675

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The Latest Highwood Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
8.2/10 Very Good! (1,766 reviews)
Property was nice and clean today

Reviewed on 25 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (2,039 reviews)
I like so much very clean,near shopping and dinning, not quiet because was near a lot people just the personal I need check the iron and blow dryer but they don’t help never

Reviewed on 25 Jun. 2025

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9/10 Wonderful! (1,123 reviews)
Great location. Nice rooms

Reviewed on 22 Jun. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (3,355 reviews)
Very comfortable hotel. Very responsive staff.

Reviewed on 25 Jun. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun. 2025

Highwood Holiday

Our pick of the best Highwood Hotel Deals

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 NZ$371 per night from 25 July to 26 July
NZ$371
25 July - 26 July
includes taxes & fees
8/10 Very Good! (2,067 reviews)
"Easy to walk out of airport into the hotel! No shuttle needed!"

Reviewed on 24 Jun. 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 NZ$240 per night from 28 June to 29 June
NZ$240
28 June - 29 June
includes taxes & fees
8.6/10 Excellent! (1,660 reviews)
"Fascinating architecture. Nice stay."

Reviewed on 23 Jun. 2025

Hyatt Regency O'Hare Chicago
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 NZ$211 per night from 6 July to 7 July
NZ$211
6 July - 7 July
includes taxes & fees
8.6/10 Excellent! (2,234 reviews)
"As was expected"

Reviewed on 23 Jun. 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,333 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.

Frequently asked questions

How much does a Highwood holiday package cost?
You'll find cheap prices from NZ$1,675 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.

Discover the most popular places to visit in Highwood

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Highwood

River tour boat in Chicago

Architecture River Tour

NZ$81
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$75
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$74
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Highwood
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.