Highwood Vacations from $238
Book a Hotel + Flight or Car together to unlock savings
Photo by Tara Jabbari
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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $468, price is now $238 per person
$238
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on Oct 4, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $531, price is now $280 per person
$280
per person
Nov 24 - Nov 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great breakfast. Very nice desk staff.
Reviewed on Oct 8, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $620, price is now $333 per person
$333
per person
Nov 24 - Nov 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on Oct 7, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,281, price is now $726 per person
$726
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on Oct 6, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,402, price is now $1,381 per person
$1,381
per person
Nov 21 - Nov 27
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Awesome room amazing tub even better service
Reviewed on Oct 2, 2025
Discover the most popular places to visit in Highwood
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highwood
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Highwood Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $164 total per night from Oct 29 to Oct 30
$164 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (2,044 reviews)
"nice"
Reviewed on Oct 7, 2025
Marriott Chicago O'Hare
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Oct 24 to Oct 25
$179 total
Oct 24 - Oct 25
Total with taxes and fees
8.4/10 Very Good! (1,157 reviews)
"Lake"
Reviewed on Oct 3, 2025
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Oct 19 to Oct 20
$108 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
"I can’t complain. I was only there one night but the place was really clean and spacious for what I paid."
Reviewed on Oct 4, 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.
Highwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 5,400 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Genesee Theater, Marriott Theatre and North Shore Center for the Performing Arts |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Chicago Hotels
- Apartments in Highwood Station
- Hotels near Highland Park Fort Sheridan Station
- Condo Rentals in Highland Park Fort Sheridan Station
- Hotels near Highland Park Country Club
- Highland Park Hotels
- Hotels near Highland Park Station
- Hotels with Connecting Rooms in Highland Park
- Extended Stay America Hotels in Highland Park
- B&B in Highland Park
- Resorts in Highland Park
- 5 Star Hotels in Highland Park
- Red Roof Inn Hotels in Highland Park
- Family Hotels in Highland Park
- Hotels with Bars in Highland Park
- Pet-friendly Hotels in Highland Park
- Hotels with Hot Tubs in Highland Park
- Extended Stay Hotels in Highland Park
- Boutique Hotels in Highland Park
- Hilton Hotels in Highland Park
- La Quinta Inn & Suites Hotels in Highland Park
- Hotels on the Lake in Highland Park
- Hotels with a Pool in Highland Park
- Hostels in Highland Park
- Condo Rentals in Highland Park
- Hyatt Hotels in Highland Park
- Hotels with a Gym in Highland Park
- Hotels with an Indoor Pool in Highland Park
- 4 Star Hotels in Highland Park
- Luxury Hotels in Highland Park
- Hotels with an Outdoor Pool in Highland Park
- Cheap Hotels in Highland Park
- 3 Star Hotels in Highland Park
- Motels in Highland Park
- Gay friendly Hotels in Highland Park
- Historic Hotels in Highland Park
- Beach Hotels in Highland Park
- Hotels with Laundry Facilities in Highland Park
- Golf Hotels in Highland Park
- Non-Smoking Hotels in Highland Park
- Hotels with Free Parking in Highland Park
- Apartments in Highland Park
- Best Western Hotels in Highland Park
- Cottages in Highland Park
- Deerfield Hotels
- Hotels near Bannockburn
- Luxury Hotels in Bannockburn
- Hotels with Restaurants in Bannockburn
- Hotels with Connecting Rooms in Bannockburn
- Cheap Hotels in Bannockburn
- Hotels with a Gym in Bannockburn
- 4 Star Hotels in Bannockburn
- Hotels with Hot Tubs in Bannockburn
- Resorts & Hotels with Spas in Bannockburn
- Historic Hotels in Bannockburn
- Extended Stay Hotels in Deerfield
- Hotels with Free Breakfast in Deerfield
- Hotels with Bars in Deerfield
- Luxury Hotels in Deerfield
- Hotels with an Indoor Pool in Deerfield
- Pet-friendly Hotels in Deerfield
- 4 Star Hotels in Deerfield
- Cheap Hotels in Deerfield
- Hotels with Kitchenettes in Deerfield
- Resorts & Hotels with Spas in Deerfield
- Best Western Hotels in Deerfield
- Romantic Hotels in Deerfield
- 5 Star Hotels in Deerfield
- Hotels with Hot Tubs in Deerfield
- Hotels with Connecting Rooms in Deerfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.