Title: Visit Highland Hills: 2026 Highland Hills, Chicago Travel Guide | Expedia.com [Hotels in Highland Hills](https://expedia.com/Highland-Hills-Chicago-Hotels.0-n6132236-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.com/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.com/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Car Rentals in Highland Hills](https://expedia.com/Car-Rentals-In-Highland-Hills.d6132236.Car-Rental-Guide)[Highland Hills Vacations](https://expedia.com/Highland-Hills.d6132236.Destination-Travel-Guides) # Highland Hills, IL ## Chicago ## Visit Highland Hills Things to do Hotels Where to stay [Chicago Travel Guide](https://expedia.com/Chicago.dx178248) --- ### Popular places to visit ![Wrigley Field featuring cbd, a sporting event and a city](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.com/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.com/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Chicago Skyline at North Beach](https://images.trvl-media.com/place/6069213/e3e08680-ba57-4e08-8e19-fef490757e5e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. [](https://expedia.com/Naval-Base-Great-Lakes-Chicago.d6069213.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.com/McCormick-Place-Near-South-Side.d6069191.Vacation-Attraction) ![Beautiful autumn colors surround modern architecture in Millennium Park, Chicago during a sunny day](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.com/Millennium-Park-Downtown-Chicago.d6069201.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.com/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### Things to do ![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 $27 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Bulls Basketball Game at United Center $66 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.activity-details) ![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 $41 per adult **94%** of travellers recommend [](https://expedia.com/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Navy Pier Centennial Wheel Ticket $25 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.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 $38 per adult **98%** of travellers recommend [](https://expedia.com/things-to-do/flyover-in-chicago.a50023979.activity-details) ![cruise ship sailing past navy pier in chicago](https://mediaim.expedia.com/localexpert/173241/21d8d1a0-e61c-4298-ab2f-118c1794b450.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### City Cruises Chicago: Lake Michigan Premier Dinner Cruise $137 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.activity-details) [See all activities in Chicago](https://expedia.com/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/1000000/20000/10700/10641/6e52464b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay Plus Hotel by Best Western Chicago Lombard 222 E 22nd Street Lombard IL $88 nightly $98 total Apr 1 - Apr 2 Total with taxes and 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! (2,641 reviews) Great staff. Able to make all accommodations requested. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=10641&PinnedHotelID=10641&HadPinnedHotel=true®ionId=6132236) ![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 $221 nightly $259 total Apr 26 - Apr 27 Total with taxes and 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! (2,243 reviews) Everything was clean and the staff was very friendly and helpful! Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=6132236) ![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 $135 nightly $154 total Apr 6 - Apr 7 Total with taxes and fees Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ... 8.8/10 Excellent! (2,435 reviews) Clean great shuttle service Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=5403&PinnedHotelID=5403&HadPinnedHotel=true®ionId=6132236) ![La Quinta Inn & Suites by Wyndham Chicago Downtown](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/b573f792_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Chicago Downtown 1 S Franklin Street Chicago IL $131 nightly $154 total Mar 29 - Mar 30 Total with taxes and fees Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 3 restaurants. Our guests praise the helpful staff and the clean ... 8.6/10 Excellent! (2,732 reviews) Rooms were very clean and tastefully decorated Reviewed on Mar 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=2506471&PinnedHotelID=2506471&HadPinnedHotel=true®ionId=6132236) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Emily Hotel 311 North Morgan Street Chicago IL $237 nightly $278 total Mar 29 - Mar 30 Total with taxes and fees Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ... 9.2/10 Wonderful! (1,329 reviews) Only complaint is the water pressure in the shower was not great. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=19381112&PinnedHotelID=19381112&HadPinnedHotel=true®ionId=6132236) ![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 $149 nightly $175 total Apr 3 - Apr 4 Total with taxes and 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! (1,234 reviews) It was all good! Reviewed on Mar 23, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F3%2F2026&endDate=4%2F4%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true®ionId=6132236) [See all 3,199 properties in Highland Hills](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F27%2F2026&endDate=3%2F28%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. ## Check Highland Hills hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=2026-03-26&endDate=2026-03-27)[Mar 26 - Mar 27](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=2026-03-26&endDate=2026-03-27) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=2026-03-27&endDate=2026-03-28)[Mar 27 - Mar 28](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=2026-03-27&endDate=2026-03-28) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132236&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) --- ### Other neighborhoods 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 4/5(783 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.com/Chicago-OHare.dx553248635074842747) ![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(107 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.com/Chicago-West-Town.dx6132439) ![606 Trail Wicker Park](https://images.trvl-media.com/place/6227639/4f7be21f-2085-45e6-ab70-172236c98d9c.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.com/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 4.5/5(751 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.com/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 Old St Patrick’s Church 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.com/Chicago-West-Loop.dx553248634029130868) ![Lakeview featuring modern architecture](https://images.trvl-media.com/place/178166/66f7ee9b-8e1a-4caa-8412-e82732aa12d8.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lakeview 4.5/5(859 area reviews) Known for its great bars and fantastic lake views, there's plenty to explore in Lakeview. You can visit top attractions like Wrigley Field and Lake Michigan, and jump on the metro at Southport Station or Addison Station (Red Line) to see more of the city. [](https://expedia.com/Chicago-Lakeview.dx178166) [See our Where To Stay guide](https://expedia.com/Chicago.dx178248.Where-To-Stay?rfrr=TG.LP.Dest.Neigh.Neighborhoods) --- --- - [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, IL ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Yorktown Shopping Center ](https://www.expedia.com/Yorktown-Shopping-Center-Hotels.0-l6227539-0.Travel-Guide-Filter-Hotels) - [Hotels near York Center ](https://www.expedia.com/York-Center-Chicago-Hotels.0-n6132296-0.Travel-Guide-Filter-Hotels) - [Lombard Hotels ](https://www.expedia.com/Lombard-Hotels.d8393.Travel-Guide-Hotels) - [Oakbrook Terrace Hotels ](https://www.expedia.com/Oakbrook-Terrace-Hotels.d9064.Travel-Guide-Hotels) - 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