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

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $279, price is now $169 per person
$169
per person
Dec 7 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Did not have breakfast

Reviewed on Oct 23, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,273 reviews)
It was a perfect spot to get anywhere in the city! Very walkable to restaurants and stores, as well as convenient access to public transportation.

Reviewed on Oct 20, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,117, price is now $680 per person
$680
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.

Reviewed on Oct 20, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $593, price is now $362 per person
$362
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $656 per person
$656
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!

Reviewed on Oct 20, 2025

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
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Jackson Park Highlands Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Nov 9 to Nov 10
$168 total
Nov 9 - Nov 10
Total with taxes and fees
7.8/10 Good! (9,555 reviews)
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

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $130 total per night from Nov 16 to Nov 17
$130 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,133 reviews)
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

Hilton Chicago/Magnificent Mile Suites
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $99 total per night from Nov 17 to Nov 18
$99 total
Nov 17 - Nov 18
Total with taxes and fees
7.8/10 Good! (2,498 reviews)
Great Vibe!

Reviewed on Oct 19, 2025

Freehand Chicago
See all 4,251 properties in Jackson Park Highlands
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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Jackson Park Highlands

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

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.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.