Hickory Hills Vacations from $215

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Your Hickory Hills Vacation

When a fun city getaway is calling, answer it with a vacation package to Hickory Hills. The neighborhood of Woodlawn, which is great for cycling, golfing and walking, makes a terrific base for your adventures. Want to explore your surroundings? SeatGeek Stadium, Chicago Ridge Shopping Mall and Burr Ridge Village Center are three of the leading places to visit during your trip to Hickory Hills. A couple of quick clicks is all it takes to build your dream Hickory Hills vacation on Expedia.

The Latest Hickory Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $416, price is now $215 per person
$215
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Everything was excellent. Will definitely stay here again. I really liked the scent of the bath/shower products and the candles in the lobby

Reviewed on Nov 20, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,175, price is now $526 per person
$526
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
Great location and staff was very accommodating. Rooms were on the small side.

Reviewed on Nov 19, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $858, price is now $463 per person
$463
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Leo handled our stay and made it seamless with first class service. Much appreciated!

Reviewed on Nov 20, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $794, price is now $443 per person
$443
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on Nov 17, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $406, price is now $227 per person
$227
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 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 Oct 28, 2025

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Discover the most popular places to visit in Hickory Hills

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
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

What to do in Hickory Hills

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Hickory Hills

Hickory Hills 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
$87 nightly
The price is $102 total per night from Dec 8 to Dec 9
$102 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (5,274 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.

Reviewed on Nov 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Dec 21 to Dec 22
$145 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,072 reviews)
Staff could not have been more helpful. The venue was packed for an international rugby game, but everything was clean, well cared for and comfortable. Will defintiely stay here again!

Reviewed on Nov 18, 2025

Palmer House a Hilton Hotel
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
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,337 reviews)
Thank you

Reviewed on Nov 20, 2025

Hilton Chicago/Magnificent Mile Suites
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.

Find the Best Hickory Hills Vacation Packages

Hickory Hills Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
14,100
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Galloping Ghost and Lizzadro Museum of Lapidary Art

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Frequently asked questions

How much does a Hickory Hills vacation package cost?
You'll find cheap prices from $215 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?
If you'd like to book a cheap Hickory Hills vacation package, consider visiting in December, January and February. You'll usually find better rates on airfares and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Hickory Hills?
Generally, a handful of days is enough to visit the major sights during your Hickory Hills vacation. But if you want to have some time to unwind or take day tours, consider extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Hickory Hills vacation packages?
Set off on your dream trip to Hickory Hills with Expedia's Book Now, Pay Later vacations. No need to save up or wait until the next payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snap up bargains before they disappear.

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