Highwood Vacations from $323

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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.
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

2.5 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (840 reviews)
The mall to go shopping was near..

Reviewed on Jun 28, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on Jun 29, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
I enjoyed every aspect of my stay here. I liked it so much the first time that I just had to stay here the second time around. The only critique that I have is that the internet is really wonky and janky to connect to. My partner and I encountered a constant connection issue whereby it would take us a longer than 5 minutes to connect to the Wi-Fi/internet for the hotel. Only after multiple retrys would the internet connection become stable.

Reviewed on Jun 30, 2025

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,873 reviews)
Everything was good. Only complaint was the hair dryer didn’t work the best but overall was satisfied.

Reviewed on Jun 30, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,094 reviews)
Convenient for early or late flights

Reviewed on Jun 30, 2025

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Discover the most popular places to visit in Highwood

Wrigley Field featuring cbd, a sporting event and a city

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.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North showing night scenes, a city and signage

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.

Michigan Avenue

What to do in Highwood

River tour boat in Chicago

Architecture River Tour

$49
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

$45
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

$45
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Highwood

Highwood Hotel Deals

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from Jul 1 to Jul 2
$193 total
Jul 1 - Jul 2
Total includes taxes and fees
8.6/10 Excellent! (1,690 reviews)
"Clean and staff are very helpful"

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
$85 nightly
The price is $96 total per night from Jul 1 to Jul 2
$96 total
Jul 1 - Jul 2
Total includes taxes and fees
7.8/10 Good! (1,279 reviews)
"In room coffee makers would be a great addition"

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
$112 nightly
The price is $127 total per night from Jul 3 to Jul 4
$127 total
Jul 3 - Jul 4
Total includes taxes and fees
8.6/10 Excellent! (2,262 reviews)
"The Rosemont Theater is right across the street. Mall and shopping within walking distance. Shuttle from and to airport. Hassle free.The frontdesk and staff were great, extremely nice and helpful."

Reviewed on Jun 29, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,332 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.

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

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Frequently asked questions

How much does a Highwood vacation package cost?
You'll find cheap prices from $323 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.