Jackson Park Highlands Vacations from ￥409,174

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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
Price was ￥503,370, price is now ￥409,174 per person
￥409,174
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on Mar 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥629,236, price is now ￥449,760 per person
￥449,760
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
Overall the experience was amazing

Reviewed on Mar 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥684,328, price is now ￥533,808 per person
￥533,808
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.

Reviewed on Mar 3, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥543,210, price is now ￥434,640 per person
￥434,640
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) 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 Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥511,058, price is now ￥414,530 per person
￥414,530
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,700 reviews)
My stay at The Wade overall was pretty good. I booked here because it has a pool, and I thought I would have a nice view (city view). The view wasn’t available, I was on the 27th floor and only had a view of the roof of other buildings, and other apartments. I kept the window covered for the most part. The pool was unkept in my opinion, I didn’t feel comfortable with the dirt ring on the white tile that surrounded the pool, and the water looked and felt pretty grimy, I felt it needed to be serviced. Though my main attractions to this location were not fulfilled it was very quiet on my floor, the cleaning crew were very polite and generous, and the valet was very friendly and always gave me great service despite it being very busy over the course of my stay.

Reviewed on Mar 2, 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
The price is ￥25,418 per night from Mar 21 to Mar 22
￥25,418
￥29,837 total
Mar 21 - Mar 22
includes taxes & fees
8/10 Very Good! (9,916 reviews)
Great location! Friendly staff

Reviewed on Mar 5, 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
The price is ￥19,220 per night from Mar 15 to Mar 16
￥19,220
￥26,984 total
Mar 15 - Mar 16
includes taxes & fees
9.4/10 Exceptional! (3,456 reviews)
We loved our spacious room and all of the staff was so kind and helpful. The breakfast every morning was amazing, and the location was perfect for all our plans in the city. We will definitely be back!

Reviewed on Mar 5, 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
The price is ￥20,464 per night from Mar 23 to Mar 24
￥20,464
￥24,022 total
Mar 23 - Mar 24
includes taxes & fees
8.6/10 Excellent! (5,715 reviews)
Old property bad food long lines

Reviewed on Mar 5, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,430 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 ￥409,174, 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
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

￥6,860
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

￥5,928
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.