Highwood Vacations from $253
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Your Highwood Vacation
Book a custom vacation package to Highwood and get ready to experience this incredible city how you like. Consider staying in the neighborhood of Riverwoods, which is good for nature and tons more. A trip to Highwood is an excellent opportunity to take in the sights. Be sure to look around renowned attractions like Chicago Botanic Garden, Lake Forest College and Marriott Theatre. No matter your travel plans or the size of your budget, putting together a tailored Highwood vacation is a breeze with Expedia.
The Latest Highwood vacation packages
Price found within the past 48 hours. Click for updated prices.
Viceroy Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,067 reviews)
The room was spacious, clean, and updated. The area was perfect to get anywhere we wanted. The staff was kind and helpful. The rooftop pool was very nice.
Reviewed on Aug 15, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
We tried the Riu Rooftop bar and it was lovely. The buffet breakfast was great. However, the weekend start time was a bit late compared to weekday. We had to check out at 7:15 and missed it. Hotel staff did not allow or offer us a small bag of pastry to go before we check out even though the 3rd person breakfast was charged
Reviewed on Aug 14, 2025
Staybridge Suites, Lincolnshire by IHG
Half Day
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
In a great neighborhood. Quiet, clean. Excellent room layout. Free laundry was very nice to have. Nice breakfast.
Reviewed on Aug 14, 2025
Discover the most popular places to visit in Highwood
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highwood
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $210 total per night from Sep 5 to Sep 6
$210 total
Sep 5 - Sep 6
Total includes taxes and fees
8.2/10 Very Good! (2,102 reviews)
"Very convenient for early/late flights, room clean, overall quiet, bed was pretty soft/low to the ground, service a little slow."
Reviewed on Aug 12, 2025
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd, Rosemont, IL
Fully refundable
$123 nightly
The price is $140 total per night from Sep 1 to Sep 2
$140 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (2,389 reviews)
"Great location to get to and from the airport and shopping mall"
Reviewed on Aug 14, 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $163 total per night from Aug 17 to Aug 18
$163 total
Aug 17 - Aug 18
Total includes taxes and fees
8.6/10 Excellent! (1,832 reviews)
"Too big"
Reviewed on Aug 13, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.