Highwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Hotel Saint Clair- Magnificent Mile

4 out of 5
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

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,563, price is now CA $1,032 per person
CA $1,032
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Had a lovely stay!

Reviewed on Aug 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
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

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $4,684, price is now CA $3,192 per person
CA $3,192
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,464, price is now CA $1,021 per person
CA $1,021
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

Ready to book your vacation to Highwood?

 

Choose your dates

Highwood Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
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

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 $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

Hilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
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
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,387 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 $38
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 $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $70
per adult
92% of travellers recommend
Chicago By Night River and Lake Cruise
See all activities in Highwood

Frequently asked questions

How much does a Highwood vacation package cost?
Offering great value package deals from CA $750 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.