Jackson Park Highlands Vacations from $314

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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $546, price is now $314 per person
$314
per person
Apr 15 - Apr 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $896, price is now $479 per person
$479
per person
Apr 15 - Apr 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $642, price is now $397 per person
$397
per person
Apr 16 - Apr 19
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was $819, price is now $509 per person
$509
per person
Apr 15 - Apr 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Every detail. The staff was amazing.

Reviewed on Jan 30, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $730, price is now $453 per person
$453
per person
Apr 15 - Apr 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Staff was amazing throughout our stay. Room very clean, property well maintained. Great location

Reviewed on Feb 1, 2026

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
$91 nightly
The price is $107 total per night from Feb 7 to Feb 8
$107 total
Feb 7 - Feb 8
Total with taxes and fees
8/10 Very Good! (9,844 reviews)
Clean room. Historic charm

Reviewed on Feb 3, 2026

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$103 nightly
The price is $120 total per night from Feb 10 to Feb 11
$120 total
Feb 10 - Feb 11
Total with taxes and fees
8.4/10 Very Good! (5,633 reviews)
Staff are goid ,clean room,just one comment M

Reviewed on Feb 3, 2026

Embassy Suites by Hilton Chicago Downtown River North
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Feb 10 to Feb 11
$105 total
Feb 10 - Feb 11
Total with taxes and fees
8.6/10 Excellent! (2,283 reviews)
It was amaizing

Reviewed on Feb 3, 2026

DoubleTree by Hilton Chicago - Magnificent Mile
See all 4,579 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.
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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
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

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

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.