Highwood Vacations
Book a Hotel + Flight together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AED 148 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Find the Best Highwood Vacation Packages
Highwood Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is AED 540 per night from May 25 to May 26
AED 540
AED 615 total
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (1,555 reviews)
"Quiet, comfortable and safe place. Clean, modern hotel"
Reviewed on 9 May 2025
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 793 per night from Jun 6 to Jun 7
AED 793
AED 931 total
6 Jun - 7 Jun
includes taxes & fees
8/10 Very Good! (2,044 reviews)
"Carpet is worn"
Reviewed on 9 May 2025
La Quinta by Wyndham Chicago O'Hare Airport
6860 Mannheim Rd, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is AED 372 per night from Jun 8 to Jun 9
AED 372
AED 423 total
8 Jun - 9 Jun
includes taxes & fees
8.4/10 Very Good! (1,406 reviews)
"Did the job for layover"
Reviewed on 8 May 2025
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.
Discover the most popular places to visit in Highwood
Wrigley Field
4.5/5(2,128 reviews)
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Six Flags Great America
4.5/5(347 reviews)
Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.