Name: Holiday Inn Chicago O'Hare – Rosemont by IHG
Price range: CA $186
Rating: 9

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.

Swissotel - Chicago

Downtown Chicago

CA $893

per person

Aug 19 - Aug 22

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (3,352 reviews)

Staff was so helpful

Reviewed on May 29, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,274

per person

Jul 17 - Jul 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (488 reviews)

Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

The Peninsula Chicago

Downtown Chicago

CA $2,676

per person

Aug 10 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,005 reviews)

Everyone was so helpful and friendly Great environment. Cleaning, room service ,breakfast A+

Reviewed on May 29, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,171

per person

Aug 19 - Aug 22

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (2,511 reviews)

Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.

Reviewed on May 28, 2026

Level Chicago - River North

Downtown Chicago

CA $1,339

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,017 reviews)

Great room with excellent views!

Reviewed on May 30, 2026

Ready to book your vacation to Highwood?

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Highwood Hotel Deals

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

CA $219

CA $250 total

Jun 28 - Jun 29

includes taxes & fees

8.8/10 Excellent! (2,591 reviews)

"Good location if you want good dining options, close to the airport, feels safe to walk around outside, area is pretty good."

Reviewed on May 29, 2026

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

CA $371

CA $436 total

Jun 19 - Jun 20

includes taxes & fees

8.4/10 Very Good! (2,304 reviews)

"It was a clean room but in AM ready to go in bathroom and who comes out of the bathroom was a large brown cockroach! Yikes!"

Reviewed on May 29, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG

6600 Mannheim Road, building 2 Rosemont IL

Fully refundable

CA $186

CA $215 total

Jun 21 - Jun 22

includes taxes & fees

9/10 Wonderful! (2,970 reviews)

"Rooms are great, the area is very accessible and the staff was very helpful. However, The parking is not free which made things less convenient. Other than that, I enjoyed my stay."

Reviewed on May 29, 2026

See all 1,484 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.

Discover the most popular places to visit in Highwood

Wrigley Field

4.5/5(159 reviews)

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

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

Naval Base Great Lakes

4.5/5(3 reviews)

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.

Michigan Avenue

4.5/5(20 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.

What to do in Highwood

360 CHICAGO Observation Deck

CA $37

per adult

86% of travellers recommend

Art Institute of Chicago

CA $55

per adult

92% of travellers recommend

Skydeck - Willis Tower Admission

CA $60

per adult

96% of travellers recommend

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.

Highwood Vacation Packages

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Your Highwood Vacation

Top Highwood Vacation Deals

Swissotel - Chicago

Level Chicago Fulton Market

The Peninsula Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

Level Chicago - River North

Ready to book your vacation to Highwood?

Highwood Hotel Deals

Hyatt Regency O'Hare Chicago

Hilton Chicago O'Hare Airport

Holiday Inn Chicago O'Hare – Rosemont by IHG

Discover the most popular places to visit in Highwood

Wrigley Field

Naval Base Great Lakes

Michigan Avenue

What to do in Highwood

360 CHICAGO Observation Deck

Art Institute of Chicago

Skydeck - Willis Tower Admission

Explore a world of travel with Expedia

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