Title: Visit Highwood: Best of Highwood Tourism | Expedia Travel Guide - 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)[Highwood Vacation Packages](https://expedia.ca/Highwood.d115190.Destination-Travel-Guides) # Highwood ## Travel Guide ![The most delicious cookies I have ever had, I'm sure you will agree!! ](https://images.trvl-media.com/place/115190/9180d4f9-8a61-426f-90dd-5f32691eae37.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![The most delicious cookies I have ever had, I'm sure you will agree!! ](https://images.trvl-media.com/place/115190/9180d4f9-8a61-426f-90dd-5f32691eae37.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Highwood Things to do ![](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=DX_SPRING_PROMO_115190) - Highwood Hotel Deals - Vacation Rentals in Highwood ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL CA $268 CA $315 total Mar 14 - Mar 15 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ... 8.2/10 Very Good! (2,222 reviews) We always enjoy staying here whenever we plan a trip where we fly out of O’Hare early. It is so convenient being connected directly to the Terminal. Reviewed on Feb 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F03%2F2026&endDate=15%2F03%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=115190) ![Marriott Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/10000/300/281/13bbda80_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott Chicago O'Hare 8535 West Higgins Road Chicago IL CA $196 CA $230 total Mar 20 - Mar 21 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ... 8.6/10 Excellent! (1,225 reviews) Cleanliness Reviewed on Feb 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true®ionId=115190) ![Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG](https://images.trvl-media.com/lodging/1000000/30000/20400/20348/9004f7ac_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG 5440 N River Rd Rosemont IL CA $158 CA $180 total Mar 2 - Mar 3 includes taxes & fees Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ... 8.6/10 Excellent! (2,745 reviews) Clean Reviewed on Feb 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=20348&PinnedHotelID=20348&HadPinnedHotel=true®ionId=115190) [See all 1,474 properties in Highwood](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=22%2F02%2F2026&endDate=23%2F02%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. ![The Gem Museum Suites](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/acb706d3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Gem Museum Suites 1555 Oak Avenue Evanston IL Book a stay at this business-friendly aparthotel in Evanston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Baha'i House of Worship ... 9.4/10 Exceptional! (104 reviews) Great stay! Initially, there was a problem with the shower and they changed our room right away. The room was spotless including the kitchen area. Breakfast was delicious. Parking was convenient, especially when using the side entrance to the hotel. We would definitely stay there again. Reviewed on Feb 2, 2026 [](https://expedia.ca/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information) ![Great Location-Beautiful Friendly Andersonville Neighborhood](https://images.trvl-media.com/lodging/23000000/22870000/22869200/22869195/a20e7b45_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Great Location-Beautiful Friendly Andersonville Neighborhood Chicago IL Stay at this apartment in Chicago. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wrigley Field and Riviera Theatre are located ... 9.8/10 Exceptional! (109 reviews) Beautiful and comfortable! My friends and I stayed here over the weekend and loved it. Convenient location within walking distance to come of the city’s best restaurants and bars. Clean, sunny and the beds were cozy! We will definitely consider staying here again. Reviewed on Dec 16, 2025 [](https://expedia.ca/Chicago-Hotels-Great-Location-Beautiful-Friendly-Andersonville-Neighborhood.h22869195.Hotel-Information) ![Cozy studio in Andersonville Chicago](https://images.trvl-media.com/lodging/116000000/115200000/115194000/115193975/d00e73e2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy studio in Andersonville Chicago Chicago IL Stay at this apartment in Chicago. Enjoy free WiFi, laundry facilities, and air conditioning. Popular attractions Wrigley Field and Riviera Theatre are located ... 9.4/10 Exceptional! (62 reviews) Host was so flexible, communicated so well, and was super accommodating. The space was welcoming and cozy. Thank you!!! Reviewed on Feb 8, 2026 [](https://expedia.ca/Chicago-Hotels-Cozy-Studio-In-Andersonville-Chicago.h115193975.Hotel-Information) [See all properties in Highwood](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=115190&sort=VACATION_RENTAL) 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. ## Check Highwood hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=115190&startDate=2026-02-21&endDate=2026-02-22)[Feb 21 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=115190&startDate=2026-02-21&endDate=2026-02-22) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=115190&startDate=2026-02-22&endDate=2026-02-23)[Feb 22 - Feb 23](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=115190&startDate=2026-02-22&endDate=2026-02-23) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=115190&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)[Feb 27 - Mar 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=115190&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026) ### Popular places to visit ![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 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 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 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) ![McCormick Place showing a high rise building and a city](https://images.trvl-media.com/place/6069191/6dd1da52-961b-4d36-a030-f105009f678b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### McCormick Place Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges. [](https://expedia.ca/McCormick-Place-Near-South-Side.d6069191.Vacation-Attraction) ![Soldier Field which includes a high-rise building, a city and modern architecture](https://images.trvl-media.com/place/6058043/a6d7265e-c5df-4d76-82e8-7937dba83c13.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Soldier Field Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations. [](https://expedia.ca/Soldier-Field-Near-South-Side.d6058043.Vacation-Attraction) ![Millennium Park featuring autumn colours, street scenes and a city](https://images.trvl-media.com/place/6069201/87d76a1e-e63f-48a2-8892-fb54ee86f8e1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Millennium Park A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape. [](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) ### Things to do ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour CA $55 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $46 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Highwood](https://expedia.ca/Things-To-Do-In-Highwood.d115190.Travel-Guide-Activities) ## Cities near Highwood ![Chicago showing a high-rise building and a city as well as a family](https://images.trvl-media.com/place/178248/719a2712-bcc7-4b9d-86cc-997f107a7839.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Chicago - Cities near Highwood - Places of interest [Chicago](https://expedia.ca/Chicago.dx178248) - [Naval Base Great Lakes ](https://expedia.ca/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction) - [Lake Michigan ](https://expedia.ca/Lake-Michigan-United-States-of-America.d6338716.Vacation-Attraction) - [Six Flags Great America ](https://expedia.ca/Six-Flags-Great-America-Chicago.d6023396.Vacation-Attraction) - [Donald E. Stephens Convention Center ](https://expedia.ca/Donald-E-Stephens-Convention-Center-Chicago.d6034944.Vacation-Attraction) - [Northwestern University ](https://expedia.ca/Northwestern-University-Chicago.d6034942.Vacation-Attraction) - [Woodfield Mall ](https://expedia.ca/Woodfield-Mall-Chicago.d6064089.Vacation-Attraction) - [Gurnee Mills ](https://expedia.ca/Gurnee-Mills-Chicago.d6140250.Vacation-Attraction) - [LEGOLAND® Discovery Center ](https://expedia.ca/LEGOLAND-Discovery-Center-Chicago.d6169680.Vacation-Attraction) - [Aragon Ballroom ](https://expedia.ca/Aragon-Ballroom-Uptown.d553248621563220754.Vacation-Attraction) - [Copernicus Center ](https://expedia.ca/Copernicus-Center-Jefferson-Park.d553248621555594799.Vacation-Attraction) - [Riviera Theatre ](https://expedia.ca/Riviera-Theatre-Uptown.d553248621555594761.Vacation-Attraction) - [Montrose Beach ](https://expedia.ca/Montrose-Beach-Uptown.d6277595.Vacation-Attraction) ![](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. 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