Title: Highwood Vacation Packages & Trips 2026 from CA $1,038 | Expedia.ca [Hotels in Highwood](https://expedia.ca/Highwood-Hotels.d115190.Travel-Guide-Hotels)[Vacation Rentals in Highwood](https://expedia.ca/Highwood-Vacation-Rentals.d115190.Travel-Guide-VacationRentals)[Highwood Car Rentals](https://expedia.ca/Car-Rentals-In-Highwood.d115190.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highwood Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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](https://www.expedia.ca/Chicago-Botanic-Garden-Chicago.d6064029.Vacation-Attraction), [Lake Forest College](https://www.expedia.ca/Lake-Forest-College-Chicago.d6156570.Vacation-Attraction) and [Marriott Theatre](https://www.expedia.ca/Marriott-Theatre-Half-Day.d553248621532659125.Vacation-Attraction). 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](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,038 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.2/10 Wonderful! (852 reviews) Clean, friendly staff Reviewed on Mar 10, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $1,253 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel Reviewed on Mar 10, 2026 ![Hyatt Place Chicago/Downtown - The Loop](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Chicago/Downtown - The Loop Downtown Chicago CA $1,461 per person May 29 - Jun 1 found 12 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,201 reviews) We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early. Reviewed on Mar 9, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $1,410 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (436 reviews) Great value, friendly staff Reviewed on Mar 8, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,633 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,844 reviews) One of the best hotels I've ever stayed at Reviewed on Mar 10, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_115190) ## Ready to book your vacation to Highwood? Choose your dates ## Highwood Hotel Deals ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL Fully refundableReserve now, pay when you stay CA $266 CA $312 total Apr 4 - Apr 5 includes taxes & fees 8.4/10 Very Good! (2,233 reviews) Clean room and business family budget Reviewed on Mar 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=115190) ![Marriott Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/10000/300/281/c9c2af9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott Chicago O'Hare 8535 West Higgins Road Chicago IL Fully refundableReserve now, pay when you stay CA $182 CA $214 total Apr 4 - Apr 5 includes taxes & fees 8.6/10 Excellent! (1,234 reviews) This place is always extremely accommodating whenever I’ve had issues flying in or flying out. Have a great shuttle service rooms are always clean and they’re very accommodating. Although the only part that needs help is the bartender I know she was very busy and it’s not always that busy. There ... Reviewed on Mar 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true®ionId=115190) ![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/2c5e0afa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency O'Hare Chicago 9300 Bryn Mawr Ave Rosemont IL Fully refundableReserve now, pay when you stay CA $183 CA $209 total Apr 6 - Apr 7 includes taxes & fees 8.8/10 Excellent! (2,406 reviews) Super weird layout. I was charged 128 dollars extra for some reason. I paid 180 off the expedia website for the room. I knew i would pay 45 dollars for parking, which was fine. Not sure what the extra 128 was for. Reviewed on Mar 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=5403&PinnedHotelID=5403&HadPinnedHotel=true®ionId=115190) [See all 1,475 properties in Highwood](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F03%2F2026&endDate=12%2F03%2F2026®ionId=115190) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Highwood ![Wrigley Field featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 4.5/5(158 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue 4.5/5(19 reviews) 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. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4.5/5(459 reviews) A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### What to do in Highwood ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck CA $36 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission CA $60 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/skydeck-willis-tower-admission.a1342523.activity-details) ![Art Institute of Chicago](https://mediaim.expedia.com/localexpert/170360/cfa59fea-c028-46b9-93be-ea78b723f52e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Art Institute of Chicago CA $55 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/art-institute-of-chicago.a170360.activity-details) [See all activities in Highwood](https://expedia.ca/things-to-do/search?rid=115190) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app