
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.

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,094, price is now CA $750 per person
CA $750
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,079 reviews)
My stay at the St. Clair Hotel was overall a good experience. The room was clean, cozy, and exactly as described. Everything was well maintained, and the hotel was in a convenient location.
There were just a couple of things that could be improved. The room did not include bottled water, and it wasn’t clear whether water was available for purchase or if guests needed to request it. It would be helpful if the hotel clarified this for future guests.
Also, I also ask about a crib for my 4-month-old baby, and I was told that cribs were not available. Since we were traveling with both a 2-year-old and a 4-month-old, this made sleeping arrangements difficult. My husband and I had to sleep separately, each with one child, which wasn’t the safest or most comfortable situation. Offering cribs, or at least making their availability clearer before booking, would be a great improvement for families traveling with infants.
Overall, we enjoyed our stay and appreciated the cleanliness and comfort of the room
Reviewed on Aug 4, 2026


Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,797, price is now CA $1,221 per person
CA $1,221
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
The hotel is beautiful. It has an amazing breakfast buffet, an amazing terrace with great drinks. The staff is super helpful and friendly. This hotel is a 10/10 for sure!
Reviewed on Aug 5, 2026

Highwood Hotel Deals

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is CA $238 per night from Aug 30 to Aug 31
CA $238
CA $271 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (2,952 reviews)
"The staff was excellent, as was the airport transfer. The hotel is very well located, close to the airport and the Fashion Outlets."
Reviewed on Aug 5, 2026

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $322 per night from Sep 4 to Sep 5
CA $322
CA $378 total
Sep 4 - Sep 5
includes taxes & fees
8.4/10 Very good! (2,371 reviews)
"."
Reviewed on Aug 5, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is CA $203 per night from Aug 24 to Aug 25
CA $203
CA $231 total
Aug 24 - Aug 25
includes taxes & fees
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.
What to do in Highwood

Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend

Chicago By Night River and Lake Cruise
CA $70
per adult
92% of travellers recommend
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.









