Jackson Park Highlands Vacations from ￥234,060

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The Latest Jackson Park Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Beautiful property, will definitely stay there again.

Reviewed on Jul 19, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Just a great property- really a 5 star experience-great location

Reviewed on Jul 20, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
An amazing property and staff. Will be coming back!

Reviewed on Jul 20, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Lovely hotel in a great area close to everything. But so noisy at night- people seem to like racing in the streets - outside our window.

Reviewed on Jul 20, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Enjoyed the stay. Rooftop bar is great!

Reviewed on Jul 20, 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
The price is ￥26,397 per night from Aug 4 to Aug 5
￥26,397
￥30,988 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (8,900 reviews)
"It was very centralized. The history made it even more interesting. It’s convenient because it’s centralized."

Reviewed on Jul 20, 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
Fully refundable
The price is ￥37,054 per night from Jul 24 to Jul 25
￥37,054
￥48,261 total
Jul 24 - Jul 25
includes taxes & fees
9/10 Wonderful! (2,071 reviews)
"Great location!"

Reviewed on Jul 19, 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 ￥21,377 per night from Aug 17 to Aug 18
￥21,377
￥25,093 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,495 reviews)
"Loved it!"

Reviewed on Jul 20, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,240 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 ￥234,060, 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 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
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
Magnificent Mile - River North showing night scenes, a city and signage

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

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,149
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,597
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,597
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
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.