Jackson Park Highlands Vacations from $267
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
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago - Schaumburg by IHG
Price was $432, price is now $267 per person
$267
per person
Apr 9 - Apr 13
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (999 reviews)
Staff was very courteous however the hotel needs to be updated. One little tiny bar of soap in the room was rather skimpy.
Reviewed on Jan 11, 2026
La Banque Hotel
Price was $1,047, price is now $540 per person
$540
per person
Apr 22 - Apr 28
found 18 hours ago
Roundtrip flight included
Houston (HOU) 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
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $726, price is now $428 per person
$428
per person
Mar 1 - Mar 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was great just the doors for entering and exiting the building were a hassle to open and push through. Not accessible easily the revolving door was the only way to get in and out and you had to manually push it. It was a heavy door and hard to push with all your stuff.
Reviewed on Jan 29, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,000, price is now $644 per person
$644
per person
Mar 1 - Mar 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on Jan 23, 2026
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $514 per person
$514
per person
Apr 22 - Apr 28
found 21 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
8.8/10 Excellent! (253 reviews)
I don't have any real complaints about the hotel, room or any of the facilities. Everything went as planned and without issues. My room was spacious, clean and comfortable. I would consider staying here again for business travel.
The area is not the best and it shows, it is a little sketchy and you need to be aware of your surroundings, especially as you enter or exit the facility. This is outside the control of the hotel, but it should be considered if you have family traveling with you.
The hotel has good safety measures in place and controlled entry, which is nice.
Overall I will stay here again and recommend it for individual business travel.
Reviewed on Nov 8, 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
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.
Jackson Park Highlands Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $107 total per night from Jan 31 to Feb 1
$107 total
Jan 31 - Feb 1
Total with taxes and fees
8/10 Very Good! (9,832 reviews)
Yes perfectly clean
Reviewed on Jan 24, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Feb 8 to Feb 9
$125 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (5,617 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.
Reviewed on Jan 28, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $156 total per night from Feb 9 to Feb 10
$156 total
Feb 9 - Feb 10
Total with taxes and fees
9.2/10 Wonderful! (3,255 reviews)
Everything was great just the doors for entering and exiting the building were a hassle to open and push through. Not accessible easily the revolving door was the only way to get in and out and you had to manually push it. It was a heavy door and hard to push with all your stuff.
Reviewed on Jan 29, 2026
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.
Discover the most popular places to visit in Jackson Park Highlands
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.
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.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.