Book Exclusive Highwood Vacation Packages

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Highwood flight + hotel packages

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for The Peninsula Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Millennium Park and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park Gold Experience, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast. Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for DoubleTree by Hilton Chicago - Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby. Discover genuine guest reviews for Trump International Hotel & Tower Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Park Hyatt Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

Top Highwood hotels deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $255 per night
CA $255
per night
May 11 - May 12
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast, and WiFi. Our guests praise the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby. Discover genuine guest reviews for Hilton Chicago O'Hare Airport, in O'Hare neighborhood, along with the latest prices and availability – book now.
Best Western At O'Hare

Best Western At O'Hare

2.5 out of 5
10300 W Higgins Road, Rosemont, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $107 per night
CA $107
per night
Apr. 25 - Apr. 26
Stay at this hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby. Discover genuine guest reviews for Best Western At O'Hare, in O'Hare neighborhood, along with the latest prices and availability – book now.
SpringHill Suites Chicago O'Hare by Marriott

SpringHill Suites Chicago O'Hare by Marriott

3 out of 5
8101 West Higgins Road, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $139 per night
CA $139
per night
May 5 - May 6
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the pool in our reviews. Popular attractions Allstate Arena and Norridge Park District are located nearby. Discover genuine guest reviews for SpringHill Suites Chicago O'Hare by Marriott, in Norwood Park neighborhood, along with the latest prices and availability – book now.
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

3 out of 5
6810 Mannheim Rd, Rosemont, IL
Free cancellation
The price is CA $164 per night
CA $164
per night
Apr. 21 - Apr. 22
Stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby. Discover genuine guest reviews for Hyatt Place Chicago/O'Hare Airport, in O'Hare neighborhood, along with the latest prices and availability – book now.
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $205 per night
CA $205
per night
Apr. 26 - Apr. 27
Stay at this business-friendly hotel in Chicago. Enjoy breakfast, a free airport shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby. Discover genuine guest reviews for Marriott Chicago O'Hare, in O'Hare neighborhood, along with the latest prices and availability – book now.
Sheraton Suites Chicago O'Hare

Sheraton Suites Chicago O'Hare

3.5 out of 5
6501 N Mannheim Rd, Rosemont, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $172 per night
CA $172
per night
Apr. 27 - Apr. 28
Stay at this business-friendly hotel in Rosemont. Enjoy breakfast, WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby. Discover genuine guest reviews for Sheraton Suites Chicago O'Hare, in O'Hare neighborhood, along with the latest prices and availability – book now.
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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.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Navy Pier

Highwood Vacations

Traveling is all about being inspired, discovering new things and collecting meaningful memories. And all of that begins with familiarizing yourself with your destination! Ready to find out a few details about Highwood?

A neighborhood in Chicago, Highwood is 25 miles (40 kilometers) to the northwest of the downtown area.

Chicago is home to 2,700,000 locals.

Places to visit in Highwood

Venturing out on the fairways is a fantastic way to stretch your legs and have a real blast. Challenge yourself with a friendly round at Highland Park Country Club. Need some more close by options? Moraine Park is a beautiful spot to chill out in if you're tired of traipsing around town. Find a bench, sit yourself down and rest your weary legs. But that's not all there is. Sure, dancing along to music over the radio is fun, but it'll never come close to the feeling of going to a climactic live performance! So why not book front-row tickets to an event at Ravinia Pavilion?

Where do you fly into for Highwood?

Pack your bags, grab your passport and prepare for a spectacular adventure. When you touch down at O'Hare International Airport (ORD), you'll be just 17 miles (27 kilometers) to the south of Highwood.

Frequently asked questions

How much are vacation packages to Highwood?
Your travel daydreams can become a reality in Highwood for as low as CA $1,022. Our affordable package deals include flights and hotels, so booking your trip will be a cinch. The only thing you’ll have to concentrate on is having an incredible time.
Where can I get the best vacation package deals for Highwood?
You can’t beat Travelocity when it comes to finding your Highwood package deal. There are at least 400 airlines and 665,000 properties worldwide to select from. Book your trip now and get ready to cross another destination off your must-visit list.
Why should I purchase my Highwood vacation bundle via Travelocity?
We’ve got 24/7 customer support, high-quality service and a Price Match Guarantee. Life’s a big journey — and we have enticing destinations for you to journey to in all four corners of the globe. Travel with us and your wallet will thank you for it.
Can I save money on my Highwood car rental if I bundle it with my hotel or flight?
Booking a Highwood vacation package with Travelocity is one of the best ways to save cold, hard cash. Combine a car, flight and hotel, or any combination of them, and enjoy great discounts. You can also throw in experiences and activities. After you’ve collected the keys to the rental car, head out of the neighborhood and find out what this place has to offer. Around 95 kilometersfrom Highwood, Milwaukee Art Museum is the ideal road trip.
What is the best time of year to go to Highwood?
If a tight budget is what’s driving your decision making, you’ll score the best deals in . is usually the dearest time of year. Most visitors come to this destination around . If you’d rather avoid peak time, visit during .
Where should I stay when visiting Highwood?
When searching for somewhere to base yourself in Highwood, the Cozy Vet's Home Discount For Naval Grad's Family Great, Safe Neighborhood is a good place to start. Many travelers make a reservation at this top option.
Can I go on vacation to Highwood at this time?
Our team has all the knowledge to help make your vacation dreams a reality, so before organizing your trip to Highwood, read through our Covid-19 Travel Advisor. Here you’ll find up-to-date info on travel restrictions, quarantine policies and other useful advice.