Name: Holiday Inn Chicago North-Evanston by IHG
Price range: CA $193
Rating: 8.6

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.

Omni Chicago Hotel

Downtown Chicago

CA $918

per person

Aug 30 - Sep 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,813 reviews)

Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable

Reviewed on Jun 23, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $1,096

per person

Aug 3 - Aug 8

found 16 hours ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

8.2/10 Very good! (2,767 reviews)

Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.

Reviewed on Jun 26, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $2,125

per person

Aug 3 - Aug 8

found 1 hour ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (504 reviews)

Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on Jun 25, 2026

The Talbott, Autograph Collection

Downtown Chicago

CA $936

per person

Aug 30 - Sep 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (126 reviews)

Always a pleasure and a great location

Reviewed on Jun 24, 2026

The Emily Hotel

Downtown Chicago

CA $1,359

per person

Sep 10 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,330 reviews)

Great location, great space in the rooms!!

Reviewed on Jun 21, 2026

Ready to book your vacation to Highwood?

Choose your dates

Highwood Hotel Deals

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

CA $181

CA $206 total

Jun 28 - Jun 29

includes taxes & fees

8.8/10 Excellent! (2,726 reviews)

"Requested more hand towels, had to wait until the next day. Thermostat light dimmed bright to dark all night, kept waking me up both nights."

Reviewed on Jun 25, 2026

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

CA $360

CA $423 total

Jul 4 - Jul 5

includes taxes & fees

8.4/10 Very good! (2,318 reviews)

"Clean room, staff were very helpful and very friendly. Restaurants and bar were on point. Great experience! Thanks Hilton Chicago O’Hare Airport!"

Reviewed on Jun 25, 2026

Holiday Inn Chicago North-Evanston by IHG

1501 Sherman Ave Evanston IL

Fully refundable

CA $193

CA $221 total

Jul 6 - Jul 7

includes taxes & fees

8.6/10 Excellent! (1,966 reviews)

"Great place to stay while visiting Chicago. Staff was very friendly and helpful. Location is great and just a quick walk to the L and the town of Evanston is very walkable. Never felt nervous or unsafe, felt like a college town. We opted to include breakfast which was nice and they had very good ..."

Reviewed on Jun 26, 2026

See all 1,459 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.