Jackson Park Highlands Vacations from ₩2,224,668

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The Latest Jackson Park Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Aug 22 - Aug 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
This was an amazing hotel, polite staff and accommodating as well.

Reviewed on Jul 12, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.

Reviewed on Jul 12, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul 12, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Aug 22 - Aug 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
Aparthotel. Like renting a condo downtown. Perfect for longer stays.

Reviewed on Jul 5, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 22 - Aug 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on Jul 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 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
The price is ₩203,578 per night from Aug 5 to Aug 6
₩203,578
₩238,981 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,941 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is ₩274,330 per night from Aug 10 to Aug 11
₩274,330
₩366,105 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,029 reviews)
"Clean, great location ."

Reviewed on Jul 12, 2025

InterContinental Chicago Magnificent Mile by IHG
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
The price is ₩208,364 per night from Aug 10 to Aug 11
₩208,364
₩244,597 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,192 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.

Frequently asked questions

How much does a Jackson Park Highlands vacation package cost?
The cheapest Jackson Park Highlands package is ₩2,224,668, so your dream trip can become a reality --- without a hefty price tag. Bundle flights, hotels, car rentals and more to customize a package suited to your travel style.
How do I get a cheap travel package to Jackson Park Highlands?
Think of all the wonderful things you could do in Jackson Park Highlands with extra cash in your pocket. Watch your savings stack up when you bundle your airfare and hotel bookings into a Jackson Park Highlands vacation package. You have plenty of choice with Expedia too. In fact, you can choose from over 550 airlines and 1,000,000 hotel options globally. Whether you're taking off with the whole family or flying solo, planning a getaway to Jackson Park Highlands is better with a package.
Where should I stay in Jackson Park Highlands?
A journey to Jackson Park Highlands isn't over until you've seen University of Chicago and Chicago Museum of Science and Industry. Stay somewhere right nearby for quick access to these famous tourist attractions.
How far in advance should I book my Jackson Park Highlands vacation?
Travelers can normally compare international airfares on Expedia within 12 months of the departure date. Booking late? With a bit of luck, it's still possible to purchase a cheaper ticket just weeks before your flight.
What does an Expedia Jackson Park Highlands travel package include?
Packages include hotels, rental cars and flights, but you can mix and match them to create your dream Jackson Park Highlands escape. You can also add on a few tours and activities once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll get discounts you won't find anywhere else.
What should I know before booking a Jackson Park Highlands travel package?
You can save big by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or sightseeing tours. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Jackson Park Highlands Expedia vacation package?
Definitely. Expedia has over 550 airline partners to select from all over the world. With all that choice, finding the right carrier to whisk you away to Jackson Park Highlands won't be difficult.
If I'm not able to travel, can I cancel my Jackson Park Highlands vacation package?
Certainly, and we're here to help. You may be able to amend or cancel your Jackson Park Highlands vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company for older bookings. If life gets in the way of your vacation, look up our Customer Service Portal for more information.

Discover the most popular places to visit in Jackson Park Highlands

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
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.