Jackson Park Highlands Holidays from AU$3,383

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Your Jackson Park Highlands Holiday

Immerse yourself in the best that Jackson Park Highlands has to offer with a Jackson Park Highlands holiday package. From its history to every other thing that makes it so fascinating, this neighbourhood will delight you from start to finish. Some popular nearby attractions to visit during your trip to Jackson Park Highlands include University of Chicago, Chicago Museum of Science and Industry and Robie House. Whatever your dream Jackson Park Highlands holiday looks like, you can turn it into reality with Expedia.

Top Holiday Package Deals in Jackson Park Highlands

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
29 Dec - 5 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We thoroughly enjoyed our stay. The staff was courteous and attentive, the room was clean, modern, and comfortable.

Reviewed on 14 Nov. 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
29 Dec - 5 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov. 2024

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
29 Dec - 5 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (2,021 reviews)
Everything was amazing

Reviewed on 16 Nov. 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
29 Dec - 5 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
Excellent , nice city room view ,

Reviewed on 15 Nov. 2024

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
29 Dec - 5 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,306 reviews)
I didn’t like that parking was expensive & there was no valet available.

Reviewed on 12 Nov. 2024

Our guide on 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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Our pick of the best 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 AU$156 per night from 24 Nov to 25 Nov
AU$156
includes taxes & fees
24 Nov - 25 Nov
7.8/10 Good! (8,090 reviews)
"Found a big cockroach in my friends room"

Reviewed on 17 Nov. 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 17 Dec to 18 Dec
AU$181
includes taxes & fees
17 Dec - 18 Dec
8.6/10 Excellent! (3,539 reviews)
"I love it the place"

Reviewed on 15 Nov. 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 17 Dec to 18 Dec
AU$175
includes taxes & fees
17 Dec - 18 Dec
8.4/10 Very Good! (3,247 reviews)
"This was perfect hotel for people traveling who want an easy and convenient stay in central chicago near the loop! Plus also loved the soap / lotion brand they use for there toiletries."

Reviewed on 15 Nov. 2024

Club Quarters Hotel, Central Loop, Chicago
See all 3,851 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Jackson Park Highlands holiday package cost?
The cheapest Jackson Park Highlands package is AU$3,383, 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.

Discover the most popular places to visit in Jackson Park Highlands

McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
United Center

United Center

5/5(8 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

United Center

Activities

Flyover in Chicago

Flyover in Chicago

AU$58
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

AU$82
Per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

AU$68
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.