Highwood Vacation Packages

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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.

Top Highwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Price was CA $1,029, price is now CA $808 per person
CA $808
per person
Aug 28 - Aug 31
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (391 reviews)
We love Wind Creek Hotel/Casino, we have been there several times. This last time the room was clean but smelled bad.

Reviewed on May 30, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,743, price is now CA $1,186 per person
CA $1,186
per person
Aug 27 - Aug 30
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,011 reviews)
I recommend 1000/10, this hotel has everything you need and the location is everything. LOVE LOVE LOVE.

Reviewed on Jun 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,668, price is now CA $1,237 per person
CA $1,237
per person
Jul 9 - Jul 12
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,121 reviews)
I absolutely loved it! I little bit noisy but close to literally everything!

Reviewed on Jun 2, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was CA $1,885, price is now CA $1,486 per person
CA $1,486
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,370 reviews)
The hotel was very clean and a great location within Chicago close to restaurants and shopping.

Reviewed on Jun 2, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,066, price is now CA $1,635 per person
CA $1,635
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
⭐⭐⭐⭐⭐ Amazing stay! Beautiful hotel, incredible views, excellent service, and a perfect location in downtown Chicago. Everything exceeded our expectations. We loved every minute of our stay and would definitely return. Highly recommended!

Reviewed on Jun 4, 2026

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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
The price is CA $221 per night from Jun 28 to Jun 29
CA $221
CA $252 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,617 reviews)
"Reasonable hotel but dislike the $"

Reviewed on Jun 5, 2026

Hyatt Regency O'Hare Chicago
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is CA $184 per night from Jun 28 to Jun 29
CA $184
CA $212 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (2,999 reviews)
"Well equipped gym. Staff were excellent. For a hotel near a large airport this is one of the best hotels I’ve stayed at"

Reviewed on Jun 5, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
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
The price is CA $353 per night from Jul 3 to Jul 4
CA $353
CA $415 total
Jul 3 - Jul 4
includes taxes & fees
8.4/10 Very Good! (2,317 reviews)
"Always a pleasure to spend a night here before an early flight."

Reviewed on Jun 4, 2026

Hilton Chicago O'Hare Airport
See all 1,477 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Discover the most popular places to visit in Highwood

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

What to do in Highwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Highwood

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