Title: Visit Highland Hills: Best of Highland Hills, Chicago Travel 2026 | Expedia Tourism - Expedia.ca [Hotels in Highland Hills](https://expedia.ca/Highland-Hills-Chicago-Hotels.0-n6132236-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Highland Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Hills.d6132236.Car-Rental-Guide)[Highland Hills Vacations](https://expedia.ca/Highland-Hills.d6132236.Destination-Travel-Guides) # Highland Hills ## Chicago ## Visit Highland Hills Things to do Hotels Where to stay [Chicago travel guide](https://expedia.ca/Chicago.dx178248) --- ### 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 Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) --- ## Highland Hills Hotel Deals ![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/w3838h2556x2y3-00664b38_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay Plus Hotel by Best Western Chicago Lombard 222 E 22nd Street Lombard IL CA $98 CA $109 total Feb 24 - Feb 25 includes taxes & fees Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ... 9/10 Wonderful! (2,572 reviews) clean. courteous Reviewed on Feb 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=10641&PinnedHotelID=10641&HadPinnedHotel=true®ionId=6132236) ![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 ... 8.4/10 Very Good! (2,229 reviews) Staff personable. Room was old & it showed. Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F03%2F2026&endDate=15%2F03%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=6132236) ![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 Fully refundableReserve now, pay when you stay 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) Everything is perfect Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true®ionId=6132236) ![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! (2,751 reviews) Wonderful staff very welcoming Reviewed on Feb 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=20348&PinnedHotelID=20348&HadPinnedHotel=true®ionId=6132236) ![Comfort Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f3b451c4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Suites Chicago O'Hare Airport 4200 North River Road Schiller Park IL CA $83 CA $95 total Feb 26 - Feb 27 includes taxes & fees Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ... 8/10 Very Good! (2,908 reviews) La habitación deja mucho que desear y el personal no hizo sus deberes de arreglar la habitación. Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=664918&PinnedHotelID=664918&HadPinnedHotel=true®ionId=6132236) ![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Chicago Dwtn - The Mart by IHG 350 West Wolf Point Plaza, Building 2 Chicago IL CA $152 CA $179 total Feb 26 - Feb 27 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ... 8.8/10 Excellent! (2,182 reviews) Everything was great. From arriving to leaving. The only one issue was, we had to lower our loud music. Didnt think our room neighbors would hear it. But they did. After that we were cautious even with the tv. That Downtown Chicago view never disappoints. Loved that we had a corner room. It just ... Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=5467&PinnedHotelID=5467&HadPinnedHotel=true®ionId=6132236) [See all 3,298 properties in Highland Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=23%2F02%2F2026&endDate=24%2F02%2F2026®ionId=6132236) 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/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-NH_SPRING_PROMO_6132236) ## Check Highland Hills hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&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=6132236&startDate=2026-02-22&endDate=2026-02-23) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=2026-02-23&endDate=2026-02-24)[Feb 23 - Feb 24](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=2026-02-23&endDate=2026-02-24) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&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=6132236&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026) --- ### Other neighbourhoods around Highland Hills ![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### O'Hare 3.5/5(38 area reviews) Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates. [](https://expedia.ca/Chicago-OHare.dx553248635074842747) ![Chicago_LoganSquare_6132429_04](https://images.trvl-media.com/place/6132429/9b00bf25-0a43-42b8-9beb-9c7c565c05fa.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Logan Square Get to know Logan Square and its many features like its breweries and live music. You might want to explore sights like Concord Music Hall and Milwaukee Avenue, and you can jump on the metro at Logan Square Station or California Station (Blue Line) to get around the city. [](https://expedia.ca/Chicago-Logan-Square.dx6132429) ![Chicago Skyline from the west side with the train](https://images.trvl-media.com/place/6132439/f88c6ed3-b251-4bec-bb60-b3e94382f91f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Town 4/5(5 area reviews) Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city. [](https://expedia.ca/Chicago-West-Town.dx6132439) ![Wicker Park Historic District, a residential neighbourhood, Chicago, Illinois, USA](https://images.trvl-media.com/place/6227639/a89281f3-851c-4c74-8025-215bb2cb4b7b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wicker Park Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area. [](https://expedia.ca/Chicago-Wicker-Park.dx6227639) ![A view of the Chicago skyline from the rooftop of the Ace Hotel in the West Loop.](https://images.trvl-media.com/place/829/1a47d60f-edf5-4e44-b25c-6a3708851864.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Near West Side 4/5(29 area reviews) Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town. [](https://expedia.ca/Chicago-Near-West-Side.dx6132434) ![Blue Hour evening cityscape in West Loop neighborhood. Long exposure, nightscape architecture. Main street in Chicago, streets in Illinois.](https://images.trvl-media.com/place/553248634029130868/e4d15962-627f-4352-9768-bd3b891abed4.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Loop Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center. [](https://expedia.ca/Chicago-West-Loop.dx553248634029130868) --- --- - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Highland Hills ![](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