Jackson Park Highlands Holidays from NZ$2,594

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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
Price was NZ$3,219, price is now NZ$2,594 per person
NZ$2,594
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.

Reviewed on 12 Nov 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,299, price is now NZ$2,678 per person
NZ$2,678
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Great trip! Will stay again.

Reviewed on 2 Nov 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,432, price is now NZ$3,407 per person
NZ$3,407
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!

Reviewed on 20 Oct 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$3,323, price is now NZ$2,689 per person
NZ$2,689
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on 9 Nov 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,062, price is now NZ$2,601 per person
NZ$2,601
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on 28 Oct 2025

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

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

Our pick of the best Jackson Park Highlands Hotel Deals

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 NZ$197 per night from 25 Nov to 26 Nov
NZ$197
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (5,232 reviews)
Clean room. Super friendly front desk staff. Complimentary drinks were a big plus! Whole property was amazing. Walking distance to everything.

Reviewed on 12 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
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 NZ$203 per night from 7 Dec to 8 Dec
NZ$203
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,243 reviews)
Large, clean spacious rooms. Convenient to shopping and restaurants. A very good bargain for the price.

Reviewed on 8 Nov 2025

Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,538 reviews)
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Reviewed on 8 Nov 2025

Get rates
Congress Plaza Hotel
See all 4,332 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 NZ$2,594, 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

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
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)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

River tour boat in Chicago

Architecture River Tour

NZ$85
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.