Hickory Hills Vacations from ₩491,260

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Hickory Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
per person
Aug 13 - Aug 15
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.4/10 Very Good! (4,263 reviews)
I like the breakfast

Reviewed on Jul 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 13 - Aug 15
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Beautiful!! Location, room, security, everything was perfect! Very classy, elegant!

Reviewed on Jul 9, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 13 - Aug 15
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
It’s a great location for walk around the beautiful downtown of Chicago. People were so helpful and friendly. Definitely I’ll consider coming back.

Reviewed on Jul 7, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 13 - Aug 15
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,097 reviews)
Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes.

Reviewed on Jul 8, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Aug 13 - Aug 15
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Great staff, very good breakfast and well located hotel. Room was clean and comfortable. My only suggestion would be to double check the utensils are clean before put them on the buffet area because I founded some residual food in a couple dishes. Other than that we have a great stay and definitely would stay here again.

Reviewed on Jul 8, 2025

Find the Best Hickory Hills Vacation Packages

Hickory Hills Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is ₩184,175 per night from Aug 5 to Aug 6
₩184,175
₩216,202 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,922 reviews)
"It’s a historical building so it does have its worn down look. Beautiful overall. I just wish it wasn’t so expensive"

Reviewed on Jul 8, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ₩284,254 per night from Aug 7 to Aug 8
₩284,254
₩377,585 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (1,998 reviews)
"The property is next to most restaurants, shopping mall and walking distance to Navy Pier"

Reviewed on Jul 7, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is ₩245,567 per night from Jul 10 to Jul 11
₩245,567
₩288,271 total
Jul 10 - Jul 11
includes taxes & fees
8.8/10 Excellent! (2,406 reviews)
"Excellent location. Only one block away from the lake as well as from the Michigan avenue (shopping area). Our room was nice and clean. I should not say room, it was like an one bedroom apartment without a kitchen. The management was very nice."

Reviewed on Jul 8, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,470 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.

Discover the most popular places to visit in Hickory Hills

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 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

Frequently asked questions

How much does a Hickory Hills vacation package cost?
You'll find cheap prices from ₩491,260 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 vacation 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 vacation packages. Bear in mind that school vacation 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 vacation 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 vacation package well in advance.
Is it cheaper to book a Hickory Hills vacation as a package?
You can enjoy significant savings on your Hickory Hills retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation 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 vacation 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.