Jackson Park Highlands Vacations from $409

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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
Save 100% on your flight
Price was $710, price is now $409 per person
$409
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
The hotel is nice. Not luxurious, not fully equipped, but well located. It is definitely understaffed since the same person handles the front office and the breakfast/drinks in the morning, and the front office and bar in the evening. But they manage well and are extremely nice. Shoutout to Marina who was very helpful. It is rather clean, though we had to request our room to be cleaned on the 2nd day as they hadn’t done it on the first day. The breakfast options are not great, only 5-6 options are available and they’re all pastries. They have some fruits as well. Overall the stay was good but I wouldn’t go back.

Reviewed on Feb 24, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,126, price is now $567 per person
$567
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amenities, staff was ok

Reviewed on Feb 25, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,080, price is now $627 per person
$627
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
From beginning to the end my stay was a 10/10. I only stayed one night but that one night was worth it.

Reviewed on Feb 24, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $946, price is now $551 per person
$551
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $965, price is now $576 per person
$576
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel is great. A lovely boutique venue. Friendly, professional and courteous staff made us feel very welcome.

Reviewed on Feb 24, 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

4 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
$93 nightly
The price is $109 total per night from Feb 27 to Feb 28
$109 total
Feb 27 - Feb 28
Total with taxes and fees
8/10 Very Good! (9,937 reviews)
Shortly after our check in when noticed our room did not have heat called the operator only to be told the hotels boiler was out, had to call a 2nd time because the toilet wouldn't flush finally when the maintenance guy came to fix the toilet he said he could get us a space heater we was so excited ...

Reviewed on Feb 26, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Mar 4 to Mar 5
$179 total
Mar 4 - Mar 5
Total with taxes and fees
9.4/10 Exceptional! (3,415 reviews)
To recessed lights in the ceiling near the windows the windows would not shut off. We tried every little light switch in the room eight ways to Sunday and could not get those recessed lights off. The only way to shut them off was to take the card out to stop the electricity in the room. But then ...

Reviewed on Feb 26, 2026

Hotel Riu Plaza Chicago
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
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $120 total per night from Mar 4 to Mar 5
$120 total
Mar 4 - Mar 5
Total with taxes and fees
8.6/10 Excellent! (5,685 reviews)
Service was great, and the staff was very kind.

Reviewed on Feb 26, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,455 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

4.5/5(2,128 reviews)

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

4.5/5(332 reviews)

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

4.5/5(4,870 reviews)

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

Navy Pier

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$166
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
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.