Highwood Vacations from $334

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $566, price is now $334 per person
$334
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $857, price is now $472 per person
$472
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,035, price is now $621 per person
$621
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Service was amazing and the location was perfect. Would definitely stay here again.

Reviewed on Jan 28, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $767, price is now $474 per person
$474
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $902, price is now $561 per person
$561
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Every detail. The staff was amazing.

Reviewed on Jan 30, 2026

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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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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
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

What to do in Highwood

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Highwood

Highwood Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $230 total per night from Feb 27 to Feb 28
$230 total
Feb 27 - Feb 28
Total with taxes and fees
8.2/10 Very Good! (2,202 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.

Reviewed on Feb 2, 2026

Hilton 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
$118 nightly
The price is $135 total per night from Feb 7 to Feb 8
$135 total
Feb 7 - Feb 8
Total with taxes and fees
8.6/10 Excellent! (2,726 reviews)
Everything was great

Reviewed on Jan 30, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $79 total per night from Feb 4 to Feb 5
$79 total
Feb 4 - Feb 5
Total with taxes and fees
8/10 Very Good! (2,841 reviews)
The staff was very friendly, the shuttle was quick and efficient. The room was very large and so clean, and it was so quiet! I would totally stay here again.

Reviewed on Jan 29, 2026

Comfort Suites Chicago O'Hare Airport
See all 1,474 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 $334 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.