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 – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul. 21, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Overall it’s a great hotel.

Reviewed on Jul. 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
First night we went to bed about 11 pm. When we got in bed it was really scratchy. Discovered a bloody mattress pad on top of the sheet below the comforter, see picture attached. The next day, we

Reviewed on Jul. 26, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Great place to stay. Very central to all the fun

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

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 $197 per night from Jul 28 to Jul 29
CA $197
CA $224 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (1,789 reviews)
"Good stop for a quick Chicago visit"

Reviewed on Jul. 25, 2025

Hyatt Regency O'Hare Chicago
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 $174 per night from Aug 4 to Aug 5
CA $174
CA $198 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,327 reviews)
"Great experience"

Reviewed on Jul. 25, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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 $246 per night from Aug 22 to Aug 23
CA $246
CA $288 total
Aug 22 - Aug 23
includes taxes & fees
8/10 Very Good! (2,078 reviews)
"Our trip was delayed in Chicago and I was glad the Hilton was so close by. We took a short walk from the terminal to the hotel and were able to get some rest before our flight the next morning. The staff was friendly and the hotel was in good condition."

Reviewed on Jul. 25, 2025

Hilton Chicago O'Hare Airport
See all 1,363 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
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Discover the most popular places to visit in Highwood

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Highwood

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & 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 $749 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.