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.
Level Chicago - River North
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 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,011 reviews)
Communication with staff/host 10/10 place clean felt safe would definitely stay again definitely worth it
Reviewed on Jun 6, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,306, price is now CA $1,594 per person
CA $1,594
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,498, price is now CA $2,522 per person
CA $2,522
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on Jun 6, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,936, price is now CA $1,401 per person
CA $1,401
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too.
Reviewed on Jun 3, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,876, price is now CA $1,378 per person
CA $1,378
per person
Aug 7 - Aug 10
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on Jun 3, 2026
Highwood Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Jun 28 to Jun 29
CA $222
CA $253 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,620 reviews)
"Very helpful, polite and nice staff. Clean and confortable rooms. Close to airport."
Reviewed on Jun 5, 2026
Holiday Inn Chicago O'Hare – Rosemont by IHG
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! (3,005 reviews)
"Missed out flight connection and stayed overnight. Got in late and out early so probably not the best view of this hotel. Only real complaint was the noise from the planes taking off being so close to the airport. The airport shuttle service was great!"
Reviewed on Jun 6, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $342 per night from Jun 28 to Jun 29
CA $342
CA $402 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (2,318 reviews)
"Always a pleasure to spend a night here before an early flight."
Reviewed on Jun 4, 2026
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.
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.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highwood
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
