Hickory Hills Holidays from AU$1,198

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Your Hickory Hills Holiday

From its highlights to its hidden delights, this city is best experienced with a Hickory Hills holiday package. Find a place to stay in Woodlawn, which is great for cycling, golfing and walking. Every trip to Hickory Hills needs a well-planned itinerary. Fill yours with big-name attractions like SeatGeek Stadium, Trinity Christian College and Chicago Ridge Shopping Mall. No matter your travel plans or budget, organising a tailored Hickory Hills holiday is simple with Expedia.

The Latest Hickory Hills Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was AU$1,419, price is now AU$1,198 per person
AU$1,198
per person
26 Sept - 28 Sept
found 15 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
8.4/10 Very Good! (3,738 reviews)
It was nice and comfortable.

Reviewed on 22 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$2,088, price is now AU$1,566 per person
AU$1,566
per person
26 Sept - 28 Sept
found 15 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,744, price is now AU$1,421 per person
AU$1,421
per person
26 Sept - 28 Sept
found 15 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was AU$1,835, price is now AU$1,498 per person
AU$1,498
per person
26 Sept - 28 Sept
found 15 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$1,744, price is now AU$1,501 per person
AU$1,501
per person
26 Sept - 28 Sept
found 15 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
I enjoyed the total experience of staying at this facility.

Reviewed on 22 Aug. 2025

Hickory Hills Holiday

Hickory Hills Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
14,100
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Brookfield Zoo, Galloping Ghost and Madison Street Theatre

Our pick of the best Hickory Hills Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$273 per night from 1 Sept to 2 Sept
AU$273
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug. 2025

The Wade
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$216 per night from 24 Aug to 25 Aug
AU$216
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (8,985 reviews)
"Nice view"

Reviewed on 23 Aug. 2025

Congress Plaza Hotel
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 AU$275 per night from 3 Sept to 4 Sept
AU$275
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on 23 Aug. 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,667 properties in Hickory Hills
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
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Discover the most popular places to visit in Hickory Hills

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
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Hickory Hills

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Hickory Hills

Frequently asked questions

How much does a Hickory Hills holiday package cost?
You'll find cheap prices from AU$1,198 on Expedia for your Hickory Hills break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your holiday to Hickory Hills costs.
What are the cheapest months to go to Hickory Hills?
Plan your getaway for the shoulder or low season and you're likely to find cheap Hickory Hills holiday packages. Bear in mind that school holiday periods and major events and festivals can impact prices, so do some research before you go.
How many days is enough for Hickory Hills?
The ideal duration for your Hickory Hills holiday depends on what you'd like to see and do. Generally, a handful of days to a week will give you enough time to tick off all the leading sights and discover some hidden treasures along the way.
How to find the best Hickory Hills package deals?
Use Expedia's handy filters to help you find some terrific Hickory Hills package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Hickory Hills package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Hickory Hills holiday as a package?
You can enjoy significant savings on your Hickory Hills retreat by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Hickory Hills?
If you've got your Hickory Hills travel dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Hickory Hills?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Hickory Hills.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Hickory Hills.
  3. Decide your trip length: Consider how long you want to spend discovering Hickory Hills. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Hickory Hills holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.