--- title: "Jackson Park Highlands Vacation Packages 2026 from $353 | Expedia" description: "Bundle Jackson Park Highlands flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels." canonical: "https://www.expedia.com/Jackson-Park-Highlands.d6132329.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-13T11:41:59Z --- # Jackson Park Highlands Vacations from $353 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 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 Jackson Park Highlands Vacation Immerse yourself in the best that Jackson Park Highlands has to offer with a Jackson Park Highlands vacation package. From its history to every other thing that makes it so fascinating, this neighborhood will delight you from start to finish. Some popular nearby attractions to visit during your trip to Jackson Park Highlands include [University of Chicago](https://www.expedia.com/University-Of-Chicago-Hyde-Park.d6064081.Vacation-Attraction), [Chicago Museum of Science and Industry](https://www.expedia.com/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction) and [Robie House](https://www.expedia.com/Robie-House-Hyde-Park.d6064059.Vacation-Attraction). Whatever your dream Jackson Park Highlands vacation looks like, you can turn it into reality with Expedia. ## The Latest Jackson Park Highlands Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/81673aca.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 14 - Jan 18** ### [Le Méridien Essex Chicago + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-14/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=35130365&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.0/10** \- Wonderful (1,001 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$507~~](https://www.expedia.com/) **$353** per traveler found 1 day ago - ![The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/w1201h1722x0y78-8f9c452e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 14 - Jan 18** ### [Hotel Riu Plaza Chicago + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-14/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102622712&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.4/10** \- Exceptional (5,699 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$688~~](https://www.expedia.com/) **$454** per traveler found 1 day ago - ![A grand lobby with a central bar, high ceilings, and classical architecture.](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/6c5eafdc.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/2099d712.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 14 - Jan 18** ### [THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-14/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23481&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **8.6/10** \- Excellent (1,002 reviews) "A" Reviewed November 12, 2026 Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$553~~](https://www.expedia.com/) **$365** per traveler found 1 day ago - ![A row of black dumbbells in a gym.](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/88f07ddf.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A rooftop lounge with outdoor seating and a city skyline view.](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 15 - Jan 18** ### [Pendry Chicago + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-15/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 3 nights **9.2/10** \- Wonderful (1,164 reviews) "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back." Reviewed November 8, 2026 Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$640~~](https://www.expedia.com/) **$441** per traveler found 1 day ago - ![An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A spacious indoor area with seating arrangements, large windows, and indoor plants.](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 15 - Jan 18** ### [The Emily Hotel + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-15/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 3 nights **9.2/10** \- Wonderful (1,360 reviews) "Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights." Reviewed November 13, 2026 Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - MDW • Nonstop MDW - ATL • Nonstop [~~$923~~](https://www.expedia.com/) **$649** per traveler found 1 day ago ## Where to stay in Jackson Park Highlands Find the best Jackson Park Highlands areas and neighborhoods for the activities you enjoy most. [Learn more about Jackson Park Highlands](https://www.expedia.com/Chicago-Jackson-Park-Highlands.dx6132329) - [Downtown Chicago](#) - [Magnificent Mile](#) - [The Loop](#) - [River North](#) - [Lincoln Park](#) ![A cityscape with tall skyscrapers and a historic tower.](https://images.trvl-media.com/place/6350699/b1dbe458-cfee-4a77-aafa-ed727f3811c2.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Downtown Chicago](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=6350699) ### Downtown Chicago The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [See properties](https://www.expedia.com/Hotel-Search?regionId=6350699) ![A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.](https://images.trvl-media.com/place/800025/6670c4dd-6c2f-482d-8f82-0db84866cc03.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by © City of Chicago [View properties in map for Magnificent Mile](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=800025) ### Magnificent Mile Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. [See properties](https://www.expedia.com/Hotel-Search?regionId=800025) ![A river with yellow boats, a bridge, and tall buildings.](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for The Loop](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=800024) ### The Loop Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. [See properties](https://www.expedia.com/Hotel-Search?regionId=800024) ![A large, historic building with a central tower and multiple windows, located near a body of water.](https://images.trvl-media.com/place/6069193/0e27114d-eb41-46f9-b005-6ab55df346d2.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for River North](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=6350695) ### River North Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. [See properties](https://www.expedia.com/Hotel-Search?regionId=6350695) ![A river with a city skyline in the background, surrounded by green trees and grass.](https://images.trvl-media.com/place/507390/bb079d23-ceff-41ef-802e-0533da68eac7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Lincoln Park](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=6059328) ### Lincoln Park Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [See properties](https://www.expedia.com/Hotel-Search?regionId=6059328) ## Jackson Park Highlands Hotel Deals ### [Sable at Navy Pier Chicago, Curio Collection by Hilton](https://www.expedia.com/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 900 E Grand, Chicago, IL, 60611, US - Location: Streeterville, 8.5 mi from Jackson Park Highlands - Star rating: 4/5 - Guest rating: 9.4/10 (Exceptional, 2760 reviews) - Price: $146 nightly, $174 total, Dec 14 - Dec 15, Total with taxes and fees ### [Best Western Grant Park Hotel](https://www.expedia.com/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) ![A modern interior with a bar area, seating, and decorative wooden panels.](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1100 S Michigan Ave, Chicago, IL, 60605, US - Location: The Loop, 7.3 mi from Jackson Park Highlands - Star rating: 2.5/5 - Guest rating: 8.2/10 (Very good, 2747 reviews) - Price: $86 nightly, $102 total, Dec 7 - Dec 8, Total with taxes and fees ### [Hilton Vacation Club Hotel Blake Chicago](https://www.expedia.com/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) ![A hotel entrance with a prominent 'MORTON' sign, a 'HOTEL BLAKE CHICAGO' sign, and a '542' address number.](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/2bf93bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 500 South Dearborn Street, Chicago, IL, 60605, US - Location: The Loop, 7.7 mi from Jackson Park Highlands - Star rating: 4/5 - Guest rating: 9.6/10 (Exceptional, 1208 reviews) - Price: $111 nightly, $132 total, Dec 10 - Dec 11, Total with taxes and fees ### [Hilton Garden Inn Chicago Downtown South Loop](https://www.expedia.com/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) ![An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 55 E 11th Street, Chicago, IL, 60605, US - Location: The Loop, 7.3 mi from Jackson Park Highlands - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 2204 reviews) - Price: $97 nightly, $114 total, Nov 23 - Nov 24, Total with taxes and fees - Review: We liked that it was dog friendly. ### [Le Méridien Essex Chicago](https://www.expedia.com/Chicago-Hotels-Hotel-Essex-Chicago.h35130365.Hotel-Information) ![A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 800 S Michigan Ave, Chicago, IL, 60605, US - Location: The Loop, 7.4 mi from Jackson Park Highlands - Star rating: 4/5 - Guest rating: 9/10 (Wonderful, 1001 reviews) - Price: $127 nightly, $151 total, Dec 7 - Dec 8, Total with taxes and fees ### [Homewood Suites by Hilton Chicago Downtown South Loop](https://www.expedia.com/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.Hotel-Information) ![A modern kitchen with a large window, a dining area, and a view of the sea.](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/d2ddfcbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 59 E. 11th Street, Chicago, IL, 60605, US - Location: The Loop, 7.3 mi from Jackson Park Highlands - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 2532 reviews) - Price: $108 nightly, $127 total, Nov 23 - Nov 24, Total with taxes and fees ### [Hyatt House Chicago/West Loop-Fulton Market](https://www.expedia.com/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information) ![A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 105 N MAY STREET, Chicago, IL, 60607, US - Location: 8.8 mi from Jackson Park Highlands - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 1309 reviews) - Price: $125 nightly, $149 total, Nov 25 - Nov 26, Total with taxes and fees - Review: Y ### [ACME Hotel Chicago, Outset Collection by Hilton](https://www.expedia.com/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information) ![A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/w5790h3840x5y0-6230cc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 15 East Ohio Street, Chicago, IL, 60611, US - Location: River North, 8.8 mi from Jackson Park Highlands - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 1964 reviews) - Price: $85 nightly, $101 total, Dec 14 - Dec 15, Total with taxes and fees 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. [See all properties in Jackson Park Highlands](https://www.expedia.com/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28®ionId=6132329&adults=2&sort=RECOMMENDED&openPlayBack=true) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.