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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $551, price is now $334 per person
$334
per person
Oct 2 - Oct 5
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (433 reviews)
This is my go to place in the south suburbs.

Reviewed on Jul 30, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $2,051, price is now $1,060 per person
$1,060
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Exceptional hotel with ideal location and nice services.

Reviewed on Aug 23, 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,279, price is now $752 per person
$752
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,207 reviews)
The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude and out. Really enjoyed the stay

Reviewed on Aug 20, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,550, price is now $926 per person
$926
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on Aug 18, 2025

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,028, price is now $657 per person
$657
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,030 reviews)
We could not have asked for a better hotel. Central location. Short walk to the museums. Close to the Red Line and grocery stores. The pool and hot tub were really nice. Great breakfast and Wednesday evening social. Clean.

Reviewed on Aug 23, 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
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
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

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
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 Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Highwood

Highwood Hotel Deals

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Sep 6 to Sep 7
$168 total
Sep 6 - Sep 7
Total with taxes and fees
8.4/10 Very Good! (1,124 reviews)
"Great amenities and very clean and friendly staff"

Reviewed on Aug 20, 2025

Marriott Chicago O'Hare
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
$179 nightly
The price is $210 total per night from Sep 13 to Sep 14
$210 total
Sep 13 - Sep 14
Total with taxes and fees
8.2/10 Very Good! (2,096 reviews)
"Within walking distance of the tram station at O'Hare International Airport. The food in the restaurant was okay--nothing to write home about."

Reviewed on Aug 22, 2025

Hilton Chicago O'Hare Airport
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
$143 nightly
The price is $163 total per night from Sep 19 to Sep 20
$163 total
Sep 19 - Sep 20
Total with taxes and fees
8.6/10 Excellent! (1,877 reviews)
"The staff was amazing, and made sure that we had access to a mini fridge for our daughter's insulin. The hotel was clean end organized- and that's hard during a convention. Can't beat the location, either!"

Reviewed on Aug 21, 2025

Hyatt Regency O'Hare Chicago
See all 1,295 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.

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