Jackson Park Highlands Vacations from NT$17,606

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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 NT$30,865, price is now NT$17,606 per person
NT$17,606
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Breakfast buffet was excellent!

Reviewed on 2026/4/15

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,938, price is now NT$42,237 per person
NT$42,237
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 2026/4/7

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$28,178, price is now NT$19,788 per person
NT$19,788
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
8.4/10 Very Good! (1,881 reviews)
The room was decent. Some of th furniture could use updated. The chair material was torn and cracked. Booked a superior room but I needed to check in earlier for a event I was attending and was provided a standard room right away. Be

Reviewed on 2026/4/15

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$36,095, price is now NT$25,608 per person
NT$25,608
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on 2026/4/14

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$26,698, price is now NT$19,350 per person
NT$19,350
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Really nice and clean. Staff were extremely friendly and helpful. Will most definitely be back.

Reviewed on 2026/4/15

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

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 NT$3,640 per night from Apr 26 to Apr 27
NT$3,640
NT$4,274 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,151 reviews)
It’s in a great location and the staff is always nice.

Reviewed on 2026/4/15

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
The price is NT$4,336 per night from Apr 26 to Apr 27
NT$4,336
NT$5,090 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,124 reviews)
Very clean

Reviewed on 2026/4/15

Hilton Chicago/Magnificent Mile Suites
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
The price is NT$4,902 per night from Apr 29 to Apr 30
NT$4,902
NT$5,755 total
Apr 29 - Apr 30
includes taxes & fees
8.6/10 Excellent! (5,840 reviews)
Room was hot , we were 6 not enough of towels breakfast good staff were great

Reviewed on 2026/4/15

Embassy Suites by Hilton Chicago Downtown River North
See all 4,377 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 NT$17,606, 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

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

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