
Jackson Park Highlands Vacations from $263
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, 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


Level Chicago – Old Town
Reviewed on Dec 25, 2025

La Banque Hotel
Reviewed on Nov 30, 2025

Waldorf Astoria Chicago
Reviewed on Jan 5, 2026
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

Hilton Chicago/Magnificent Mile Suites
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.
Reviewed on Jan 6, 2026

Hilton Chicago
The hotel property was amazing! Numerous options for dining and relaxing. The room was clean and inviting.
Reviewed on Jan 8, 2026

Palmer House a Hilton Hotel
Room was very clean and staff was great
Reviewed on Jan 6, 2026
Discover the most popular places to visit in Jackson Park Highlands

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.

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

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

Skydeck - Willis Tower Admission

Chicago Bulls Basketball Game at United Center
























