
Jackson Park Highlands Vacations from $169
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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, Chicago Museum of Science and Industry and Robie House. Whatever your dream Jackson Park Highlands vacation looks like, you can turn it into reality with Expedia.
The Latest Jackson Park Highlands Vacation Packages


Hotel Felix River North/Magnificent Mile
Reviewed on Oct 20, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 20, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Reviewed on Oct 4, 2025

Park Hyatt Chicago
Reviewed on Oct 20, 2025
Where to stay in Jackson Park Highlands

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.
Jackson Park Highlands Hotel Deals

Congress Plaza Hotel
My room was spotless and comfortable. The only complaint I have is that breakfast was buffet only, not a menu, so you pay $35 even if you just want toast and some eggs. Also, they were too short-staffed to do in-room dining and were out of a lot of food items. The lake view rooms are super nice, ...
Reviewed on Oct 23, 2025

Hilton Chicago/Magnificent Mile Suites
Great place to stay in the city!!! The room was super nice with an amazing city view and the end was just perfect !!! Housekeeping staff was outstanding and it was in a very downtown convenient area to walk and find everything around !!! Would come back for sure 10000%
Reviewed on Oct 23, 2025

Freehand Chicago
Great Vibe!
Reviewed on Oct 19, 2025
Discover the most popular places to visit in Jackson Park Highlands

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

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.

Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Skydeck - Willis Tower Admission
