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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,466, price is now CA $938 per person
CA $938
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
I stayed the night after having a surgical procedure. The staff was helpful and made everything very convenient. I was able to rest comfortably. Thank you.

Reviewed on Jul 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,798, price is now CA $1,754 per person
CA $1,754
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)
Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!

Reviewed on Jul 17, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,039, price is now CA $1,380 per person
CA $1,380
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,653, price is now CA $1,151 per person
CA $1,151
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Excellent location. Staff very nice. Room big and bed very comfortable. But noisy. As is all of Chicago. Trying to sell in room soap products for exorbitant prices tachy as hell. Rooftop lounge had sadly very short hours and limited open days. Seems a shame to waste such an opportunity.

Reviewed on Jul 14, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,884, price is now CA $1,313 per person
CA $1,313
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)

Ready to book your vacation to Highwood?

 

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Highwood Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Aug 8 to Aug 9
CA $251
CA $286 total
Aug 8 - Aug 9
includes taxes & fees
Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $329 per night from Aug 16 to Aug 17
CA $329
CA $387 total
Aug 16 - Aug 17
includes taxes & fees
Hilton Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Fully refundable
The price is CA $153 per night from Jul 19 to Jul 20
CA $153
CA $176 total
Jul 19 - Jul 20
includes taxes & fees
Comfort Suites Chicago O'Hare Airport
See all 1,377 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Highwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Highwood

Frequently asked questions

How much does a Highwood vacation package cost?
Offering great value package deals from CA $938 on Expedia, you'll be pleasantly surprised at how much a vacation to Highwood costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Highwood?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Highwood vacation packages and you could land some great off-season deals.
How many days is enough for Highwood?
Allow around 2 days for your Highwood vacation if you're hoping to immerse yourself in everything that makes this place unique. Wander around key neighbourhoods, including Riverwoods and Bannockburn. Then check out top sights such as Marriott Theatre and Highland Park Country Club. With a well-planned itinerary, you'll be kept busy with room for some rest time too. Want to travel beyond Highwood? Consider an excursion or two.
How to find the best Highwood package deals?
Bagging a cheap Highwood package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most economical Highwood package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Highwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still have the freedom to create a personalized Highwood vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Highwood?
Secure incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Highwood vacation.
How to plan a trip to Highwood?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit Highwood.
  2. Budget wisely: On top of the price of your stay, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Highwood.
  3. Decide your trip length: Think about how long you want to spend discovering Highwood. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Highwood vacation package.

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.