Jackson Park Highlands Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 when you book a flight and hotel together*
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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
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Jackson Park Highlands
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
฿5,307
฿6,310 total
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (5,434 reviews)
"I really love this hotel and is close to everything just walking a couple minutes."
Reviewed on 17 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
฿5,378
฿6,394 total
27 Sept - 28 Sept
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
฿5,801
฿6,896 total
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,157 reviews)
"Grand old hotel. Worth seeing … but getting old."
Reviewed on 17 Sept 2026
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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
฿1,545
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.