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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,367, price is now CA $1,530 per person
CA $1,530
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great hotel had a great time..planning to stay again real soon…home away from home
Reviewed on Apr 16, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $2,032, price is now CA $1,384 per person
CA $1,384
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,434, price is now CA $1,746 per person
CA $1,746
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
The best hotel I've ever stayed in.
Please get an iron, please get a microwave. And please don’t charge for every single thing! ❤️
Reviewed on Apr 13, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,676, price is now CA $1,924 per person
CA $1,924
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
The check in process was a little crazy, can’t say I have ever needed a background check to stay somewhere so it was a bit time consuming although I suppose good to know safety is a priority. View from property was the best part hands down! Cost of overall stay was great deal, parking for $65 a night was a bit disappointing because it is nice to have it on site. Overall would stay again.
Reviewed on Apr 14, 2026
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $337 per night from May 8 to May 9
CA $337
CA $395 total
May 8 - May 9
includes taxes & fees
8.4/10 Very Good! (2,277 reviews)
I would rate this hotel as good to excellent if not for one employee. I stayed two nights and all the staff including front desk, restaurant and housekeeping were customer friendly and efficient with one exception. I returned back to the main entrance of the hotel on the second night after a long ...
Reviewed on Apr 12, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Apr 22 to Apr 23
CA $198
CA $225 total
Apr 22 - Apr 23
includes taxes & fees
8.8/10 Excellent! (2,487 reviews)
The room was clean. The staff had a little trouble, figuring out that we were two separate parties in two separate rooms with one reservation. It took them forever to bring a water kettle to the room.
Reviewed on Apr 16, 2026
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Apr 30 to May 1
CA $258
CA $303 total
Apr 30 - May 1
includes taxes & fees
8.6/10 Excellent! (1,235 reviews)
amenities were great and the Staff was welcoming.
Reviewed on Apr 9, 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
Skydeck - Willis Tower Admission
CA $60
per adult
98% of travellers recommend
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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.
