Jackson Park Highlands Packages (Flight + Hotel)

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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 featuring 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

Top hotels in Jackson Park Highlands

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 ฿4,142 per night from 16 Nov to 17 Nov
฿4,142
฿4,863 total
16 Nov - 17 Nov
includes taxes & fees
8.4/10 Very Good! (5,146 reviews)
This was my first time visiting Chicago. The stay far exceeded my expectations. The staff were so friendly my favorite was Arnold. The evening reception was a nice little addition to a wonderful stay. I did observe a guest lick the spoon and put it back in the hummus, zero stars gor him that was ...

Reviewed on 24 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ฿5,563 per night from 2 Nov to 3 Nov
฿5,563
฿6,531 total
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,541 reviews)
We had 4 adults in the Family Suite plenty of room. Could use larger TV's. We requested more towels and coffee and were delivered promptly.

Reviewed on 22 Oct 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿2,620 per night from 10 Nov to 11 Nov
฿2,620
฿3,651 total
10 Nov - 11 Nov
includes taxes & fees
7.8/10 Good! (2,527 reviews)
The lights is too dark in the room

Reviewed on 25 Oct 2025

Freehand Chicago
See all 4,306 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 holiday package cost?
The cheapest Jackson Park Highlands package is , 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 holiday 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 holiday?
Travellers 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 holiday 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 holiday package?
Certainly, and we're here to help. You may be able to amend or cancel your Jackson Park Highlands holiday 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 holiday, look up our Customer Service Portal for more information.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

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

Millennium Park

Things to do

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

฿1,438
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

฿3,465
per adult
84% of travellers recommend
Chicago C3® by CityPASS®
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

฿1,471
per adult
98% of travellers recommend
Chicago Sightseeing River and 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.