Jackson Park Highlands Holidays

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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.

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Aug 6 - Aug 8

    Chicago Marriott Suites Deerfield + Flight

    Deerfield
    2 nights
    4.0 star property
    8.6/10 - Excellent (1,009 reviews)
    "The staff was very helpful"
    Reviewed June 8, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$2,360
    AU$2,271
    per traveller
    found 1 day ago
    Chicago Marriott Suites Deerfield
  • Smart TV
    Aug 6 - Aug 7

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    1 night
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 2 stops ORD - SYD • 2 stops
    AU$2,760
    AU$2,634
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
    Aug 6 - Aug 7

    Nobu Hotel Chicago + Flight

    Downtown Chicago
    1 night
    5.0 star property
    9.4/10 - Exceptional (864 reviews)
    "Beautiful"
    Reviewed June 8, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 2 stops ORD - SYD • 2 stops
    AU$2,757
    AU$2,660
    per traveller
    found 1 day ago
    Nobu Hotel Chicago
  • Lobby
    Aug 6 - Aug 8

    Embassy Suites by Hilton Chicago Lombard Oak Brook + Flight

    Lombard
    2 nights
    3.5 star property
    8.2/10 - Very good (1,616 reviews)
    "Very nice staff. Great breakfast. Security to make you feel safe."
    Reviewed June 7, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$2,362
    AU$2,287
    per traveller
    found 1 day ago
    Embassy Suites by Hilton Chicago Lombard Oak Brook
  • Bar (on property)
    Aug 6 - Aug 8

    Wyndham Garden Schaumburg Chicago Northwest + Flight

    Schaumburg
    2 nights
    3.0 star property
    6.8/10 - (1,007 reviews)
    "My stay was great"
    Reviewed June 2, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$2,351
    AU$2,284
    per traveller
    found 1 day ago
    Wyndham Garden Schaumburg Chicago Northwest

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

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

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$229 per night from 29 June to 30 June
AU$229
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,212 reviews)
"Cool hotel, good history"

Reviewed on 8 June 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is AU$256 per night from 28 June to 29 June
AU$256
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,539 reviews)
"They were awesome to clean our room before we checked out . Which we checked out 2 days later"

Reviewed on 8 June 2026

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$278 per night from 29 June to 30 June
AU$278
29 June - 30 June
includes taxes & fees
8.2/10 Very Good! (1,566 reviews)
"We just stayed one night but the hotel served its purpose. We would stay here again. We also liked the lobby of the hotel and bar"

Reviewed on 8 June 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,264 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.
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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.

Discover the most popular places to visit in Jackson Park Highlands

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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
Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$64
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of 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.