Title: Jackson Park Highlands Travel Guide: Best of Jackson Park Highlands, Chicago Travel 2026 | Expedia.co.uk [Hotels in Jackson Park Highlands](https://expedia.co.uk/Jackson-Park-Highlands-Hotels.d6132329.Travel-Guide-Hotels)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Jackson Park Highlands Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Jackson-Park-Highlands.d6132329.Car-Hire-Guide)[Jackson Park Highlands Holidays](https://expedia.co.uk/Jackson-Park-Highlands.d6132329.Holidays-City-Breaks) # Jackson Park Highlands Travel Guide ## Chicago ## Visit Jackson Park Highlands Things to do Hotels Where to stay [Chicago travel guide](https://expedia.co.uk/Chicago.dx178248) --- ### Popular places to visit ![Wrigley Field featuring a city, a sporting event and city views](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.co.uk/Wrigley-Field-Lakeview.d6034754.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 find the perfect gifts to bring home 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.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.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.co.uk/Navy-Pier-Downtown-Chicago.d6069215.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.co.uk/McCormick-Place-Near-South-Side.d6069191.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.co.uk/Soldier-Field-Near-South-Side.d6058043.Attraction) ![Millennium Park which includes autumn colours, modern architecture and street scenes](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.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction) ### Things to do ![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 £18 per adult **88%** of travellers recommend [](https://expedia.co.uk/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 £28 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/flyover-in-chicago.a50023979.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 £30 per adult **94%** of travellers recommend [](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Chicago C3® : Save on admission to your choice of 3 top attractactions](https://mediaim.expedia.com/localexpert/46362450/da44d619-18fc-4969-97e2-f7b8d0da99b5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago C3® by CityPASS® £77 per adult **90%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.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 £25 per adult **96%** of travellers recommend [](https://expedia.co.uk/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Chicago: City Minibus Tour with Optional Architecture Cruise](https://mediaim.expedia.com/localexpert/4556313/67d8adf7-64e5-458d-bd4c-e2cc830c3f09.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: City Minibus Tour with Optional Architecture Cruise £36 per adult **96%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-city-minibus-tour-with-optional-architecture-cruise.a4556313.activity-details) [See all activities in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) --- ## Top hotels in Jackson Park Highlands ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL £152 14 Feb - 15 Feb includes taxes & fees Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ... 8/10 Very Good! (9,881 reviews) Great location, beautiful historic hotel with clean, updated rooms. Reviewed on 11 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=14%2F02%2F2026&endDate=15%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132329) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Plaza Chicago 150 East Ontario Street Chicago IL £123 4 Mar - 5 Mar includes taxes & fees Stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free Wi-Fi and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk ... 9.4/10 Exceptional! (3,327 reviews) The great customer service, clean room, and enjoyed the free breakfast. Reviewed on 11 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=6132329) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL £88 22 Feb - 23 Feb includes taxes & fees Stay at this hotel in Chicago. Enjoy free breakfast, room service and a fitness centre. Our guests praise the breakfast and the pool in their reviews. Popular ... 8.6/10 Excellent! (5,651 reviews) Staff was very warm and welcoming. Breakfast was delicious. The pool was very nice but needs to be shocked every week or after alot of swimmers have been in the pool! Absolutely loved valet, that was definitely a plus. And most of everything you wanna do in Chicago is right next to the hotel!! Reviewed on 11 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132329) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL £141 21 Feb - 22 Feb includes taxes & fees Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a health club. Our guests praise the helpful staff and the clean ... 8.4/10 Very Good! (2,615 reviews) Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant ... Reviewed on 8 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=6132329) ![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Aloft Chicago Mag Mile 243 E. Ontario Chicago IL £73 22 Feb - 23 Feb includes taxes & fees Stay at this hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the pool and the helpful staff in their reviews. ... 8.6/10 Excellent! (3,063 reviews) The room was okay Reviewed on 10 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=26998765&PinnedHotelID=26998765&HadPinnedHotel=true®ionId=6132329) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL £77 18 Feb - 19 Feb includes taxes & fees Stay at this business-friendly hotel in Chicago. Enjoy a fitness centre, valet parking (surcharge) and a 24-hour front desk. Our guests praise the helpful staff ... 9/10 Wonderful! (3,789 reviews) Spacious. Clean and great location Reviewed on 11 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=18%2F02%2F2026&endDate=19%2F02%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6132329) [See all 4,542 properties in Jackson Park Highlands](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=13%2F02%2F2026&endDate=14%2F02%2F2026®ionId=6132329) 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-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=DX-NH_SPRING_PROMO_6132329) ## Check Jackson Park Highlands hotel availability [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=2026-02-12&endDate=2026-02-13)[12 Feb - 13 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=2026-02-12&endDate=2026-02-13) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=2026-02-13&endDate=2026-02-14)[13 Feb - 14 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=2026-02-13&endDate=2026-02-14) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[13 Feb - 15 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[20 Feb - 22 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132329&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) --- ### Other neighbourhoods around Jackson Park Highlands ![Chicago_NearSouthSide_6132399_02](https://images.trvl-media.com/place/6132399/bed0102f-0e70-4cb1-8baa-b00fec33aaca.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Near South Side Travellers choose Near South Side for its ample dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field. [](https://expedia.co.uk/Chicago-Near-South-Side.dx6132399) ![South Loop which includes a city and a high-rise building](https://images.trvl-media.com/place/6130108/f1bd0360-1400-4c1c-882e-1779972b657f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### South Loop 3/5(3 area reviews) Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops. [](https://expedia.co.uk/Chicago-South-Loop.dx6130108) ![Beautiful fireworks](https://images.trvl-media.com/place/829/1a8abde0-c15d-4b25-9c4c-74d2678f7428.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Theatre District While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line). [](https://expedia.co.uk/Chicago-Theatre-District.dx651190586167894016) ![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(187 area reviews) Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries. [](https://expedia.co.uk/Chicago-The-Loop.dx800024) ![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(14 area reviews) Live music, theatres and shopping highlight some notable features of Near West Side. Make a stop by Credit Union 1 Arena or United Center while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town. [](https://expedia.co.uk/Chicago-Near-West-Side.dx6132434) ![Downtown Chicago featuring a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Chicago Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city. [](https://expedia.co.uk/Chicago-Downtown-Chicago.dx6350699) --- --- - [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) # Jackson Park Highlands Travel Guide ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Other - [Gay-Friendly Hotels in Armour Square ](https://www.expedia.co.uk/Armour-Square-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132365-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Avalon Park ](https://www.expedia.co.uk/Avalon-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132379-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Avalon Park Hotels ](https://www.expedia.co.uk/Avalon-Park-Chicago-Hotels.0-n6132379-0.Travel-Guide-Filter-Hotels) - [Bronzeville Hotels ](https://www.expedia.co.uk/Bronzeville-Chicago-Hotels.0-n6132245-0.Travel-Guide-Filter-Hotels) - 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[Visit Printers Row ](https://www.expedia.co.uk/Chicago-Printers-Row.dx6130106) - [Visit River North ](https://www.expedia.co.uk/Chicago-River-North.dx6350695) - [Visit South Commons ](https://www.expedia.co.uk/Chicago-South-Commons.dx6132263) - [Visit South Loop ](https://www.expedia.co.uk/Chicago-South-Loop.dx6130108) - [Visit The Loop ](https://www.expedia.co.uk/Chicago-The-Loop.dx800024) - [Visit Theatre District ](https://www.expedia.co.uk/Chicago-Theatre-District.dx651190586167894016) - [Visit West Elsdon ](https://www.expedia.co.uk/Chicago-West-Elsdon.dx6132410) - [Visit Chicago ](https://www.expedia.co.uk/Chicago.dx178248) - [Essex Holidays ](https://www.expedia.co.uk/Essex.d6132371.Holidays-City-Breaks) - [Hyde Park Holidays ](https://www.expedia.co.uk/Hyde-Park.d117842.Holidays-City-Breaks) - [Visit Riverdale ](https://www.expedia.co.uk/Riverdale.dx6132178) - [Robie House ](https://www.expedia.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) - [Visit Rush Street ](https://www.expedia.co.uk/Rush-Street.dx6175183) - [Visit South Side ](https://www.expedia.co.uk/South-Side.dx553248635074842823) - [Car hire near Lake Meadows Park ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lake-Meadows-Park.d6132351.Car-Hire-Guide) - [Enterprise Rental Cars in Hyde Park ](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Hyde Park ](https://www.expedia.co.uk/Europcar-Car-Rentals-In-Hyde-Park.d117842-c14.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in North Pullman ](https://www.expedia.co.uk/Hertz-Car-Rentals-In-North-Pullman.d6132407-c40.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in Far Southeast Side ](https://www.expedia.co.uk/Sixt-Car-Rentals-In-Far-Southeast-Side.d553248635976475411-c35.Car-Rental-Guide-Suppliers) - [Things to do in South Side ](https://www.expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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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