Highwood Vacations from $588
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$588
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,128 reviews)
The room was very clean and nice! Beds were comfortable.
Location is perfect for walking around and exploring the city!
Reviewed on Aug 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$876
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on Aug 26, 2026
What to do in Highwood
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$226 nightly
$265 total
Aug 29 - Aug 30
Total with taxes and fees
8.4/10 Very Good! (2,446 reviews)
"Very convenient, helpful staff"
Reviewed on Aug 26, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$179 nightly
$204 total
Sep 7 - Sep 8
Total with taxes and fees
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
$127 nightly
$145 total
Aug 30 - Aug 31
Total with taxes and fees
8.6/10 Excellent! (2,914 reviews)
"Staff was great and room was clean. My biggest complaint is not really the hotels fault but why is the pool open at 5am? There were young men having a party at 5:15am. If youre going to allow pool access that early, soundproof the windows because now everyone facing the pool is being disturbed."
Reviewed on Aug 25, 2026
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.
Find the Best Highwood Vacation Packages
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
How much does a Highwood vacation package cost?
You'll find cheap prices from $588 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're likely to find lower prices and greater availability in December, January and February. Check out our cheap Highwood vacation packages and you could get some great off-season discounts.
How many days is enough for Highwood?
With a well-planned itinerary, you can easily visit the top Highwood sights in a handful of days. But if you prefer to venture off the beaten track or go on day tours, think about 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.
Does Expedia offer Book Now, Pay Later Highwood vacation packages?
Set off on your ideal getaway to Highwood with help from our Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up travel deals while they last.
Explore a world of travel with Expedia
- Merchandise Mart
- Apollo Theater Chicago
- Second City
- Picasso Statue
- Elks Veterans Memorial
- Our Lady of Lourdes Church
- Six Flags Great America
- Ravinia Pavilion
- Park West
- St. Clements Church
- Dave & Buster's
- Cooking & Hospitality Institute of Chicago
- Woodfield Mall
- Marina City
- Chicago Vacations
- Depaul University-Lincoln Park
- Northwestern Memorial Hospital
- Home Alone House
- Monique Meloche Gallery
- Lighthouse ArtSpace Chicago
- Rosalind Franklin University of Medicine and Science
- Holy Trinity Russian Orthodox Cathedral
- Lincoln Park Zoo
- Depaul Art Museum
- Wrigley View Rooftop
- Graceland Cemetery
- Chicago Children's Museum
- Lincolnshire Vacations
- International Museum of Surgical Science
- Briar Street Theatre
- Lincoln Park
- Naval Base Great Lakes
- Montrose Beach
- Unity Temple
- Gorilla Tango Theatre
- Marshall Field Building
- Rookery
- St. Josaphat Church
- Hutchinson Street Historic District
- Cyrus McCormick Mansion
- Deerfield Vacations
- Asylum Skate Park
- Defiant Theatre
- Lambs Farm
- Advocate Illinois Masonic Medical Center
- Fourth Presbyterian Church
- Carbide and Carbon Building
- Edgewater Vacations
- South Pond
- The Salt Shed
- Lake Forest College
- Annunciation Greek Orthodox Cathedral
- Shops at North Bridge
- Humboldt Park
- St. John Cantius Church
- Lakeview Vacations
- Northbrook Vacations
- Illinois Centennial Memorial Column
- Michigan Avenue
- Navy Pier
- Willis Tower
- Armitage Avenue
- Farm-In-The-Zoo
- Northalsted Vacations
- Lincoln Park Vacations
- Vic Theatre
- Baha'i House of Worship
- Wrigley Building
- 900 North Michigan Shops
- Tribune Tower
- Wrigley Field
- Goose Island Vacations
- Northwestern University
- Riviera Theatre
- Henry Gerber House
- Art Institute of Chicago
- Holy Name Cathedral
- Techny Vacations
- Marriott Theatre
- Cadillac Palace Theatre
- Goodman Theater
- Depaul University-Loop Campus
- Ravinia Park
- Chicago City Hall
- Chicago Place Mall
- Rosewood Beach
- University of Illinois Chicago
- Legoland® Discovery Center
- Magnificent Mile Vacations
- Flat Iron Building
- Gold Coast Vacations
- Louis A. Weiss Memorial Hospital
- St Nicholas Ukrainian Catholic Cathedral
- Garfield Park
- Driehaus Museum
- Wicker Park Vacations
- Saint Joseph Hospital
- Chicago Botanic Garden
- Skydeck Ledge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
