Highwood Trips (flight + hotel)

Photo by Tara Jabbari
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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Highwood

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is P9,521 per night from Jul 2 to Jul 3
P9,521
P10,852 total
Jul 2 - Jul 3
includes taxes & fees
8.6/10 Excellent! (1,695 reviews)
"Super helpful staff and very accommodating!"

Reviewed on Jun 30, 2025

Hyatt Regency O'Hare Chicago
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
3.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is P4,788 per night from Jul 27 to Jul 28
P4,788
P5,410 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,280 reviews)
"Very nice"

Reviewed on Jun 29, 2025

Super 8 by Wyndham Chicago O'Hare Airport
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 P6,295 per night from Jul 6 to Jul 7
P6,295
P7,175 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (2,266 reviews)
"The staff at as very nice and helpful. The ice machine next door was flooding and had a pile of towels laying there. The carpet in the bedroom was very wet near the window."

Reviewed on Jun 30, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,338 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 vacation 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 vacation 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 vacation packages and you could land some great off-season deals.
How many days is enough for Highwood?
With a well-organized 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 vacation 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 vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights separately. Better still, you can personalize 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 vacation 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, favorite 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 vacation. 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 vacation package that brings all your bookings together.

Popular places to visit

McCormick Place

McCormick Place

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
Millennium Park showing modern architecture, autumn leaves 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
Six Flags Great America which includes 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

P2,740
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

P2,507
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

P2,507
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.