Highwood Holidays

Photo by Tara Jabbari

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Top Highwood Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Sept - 12 Sept
found 24 hours ago
Return direct flight included
San Francisco (SFO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Great gym ,great location, ,everything is great

Reviewed on 27 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Oct - 15 Oct
found 2 hours ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Great hotel! New build-out, spacious and clean, friendly staff. Excellent breakfast area with

Reviewed on 27 Jul 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Oct - 15 Oct
found 2 hours ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on 21 Jul 2025

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
10 Oct - 15 Oct
found 2 hours ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Very nicely decorated. The room was pretty small and didn’t have a small fridge. Was glad we brought a cooler.

Reviewed on 28 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Sept - 12 Sept
found 24 hours ago
Return direct flight included
San Francisco (SFO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Top hotels in Highwood

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 HK$1,407 per night from 22 Aug to 23 Aug
HK$1,407
HK$1,652 total
22 Aug - 23 Aug
includes taxes & fees
8/10 Very Good! (2,077 reviews)
"Our trip was delayed in Chicago and I was glad the Hilton was so close by. We took a short walk from the terminal to the hotel and were able to get some rest before our flight the next morning. The staff was friendly and the hotel was in good condition."

Reviewed on 25 Jul 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 HK$1,128 per night from 3 Aug to 4 Aug
HK$1,128
HK$1,285 total
3 Aug - 4 Aug
includes taxes & fees
8.6/10 Excellent! (1,801 reviews)
"The room we reserve had a very bad odor coming out from the toilet pipes and was very bad. Our family did not enjoy the room so we had to close the bathroom doors but still smelling bad"

Reviewed on 27 Jul 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 HK$997 per night from 4 Aug to 5 Aug
HK$997
HK$1,136 total
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (2,346 reviews)
"Everything"

Reviewed on 28 Jul 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,357 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.

Popular places to visit

Soldier Field featuring modern architecture, a city and a high-rise building

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
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
Six Flags Great America showing rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Highwood

River tour boat in Chicago

Architecture River Tour

HK$383
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

HK$353
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

HK$353
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Highwood

Frequently asked questions

How much does a Highwood holiday package cost?
You'll find cheap prices from HK$7,560 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.