Hickory Hills Vacations from $347

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $630, price is now $347 per person
$347
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast, Clean room, enjoyed the stay

Reviewed on Jan 9, 2026

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 $943, price is now $575 per person
$575
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $844, price is now $525 per person
$525
per person
Mar 7 - Mar 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $769, price is now $490 per person
$490
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Great location. Good size room. Restaurant was awesome.

Reviewed on Jan 9, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $648, price is now $441 per person
$441
per person
Mar 9 - Mar 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

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Discover the most popular places to visit in Hickory Hills

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
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
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 - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$83
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Hickory Hills

Hickory Hills Hotel Deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 17 to Jan 18
$192 total
Jan 17 - Jan 18
Total with taxes and fees
8.4/10 Very Good! (2,507 reviews)
Clean, good breakfast, quiet. Easy acces

Reviewed on Jan 9, 2026

Hilton Chicago
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
$168 nightly
The price is $192 total per night from Jan 17 to Jan 18
$192 total
Jan 17 - Jan 18
Total with taxes and fees
8.4/10 Very Good! (2,223 reviews)
Room was very clean and staff was great

Reviewed on Jan 6, 2026

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
$89 nightly
The price is $105 total per night from Jan 18 to Jan 19
$105 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (3,677 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on Jan 7, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,727 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 $347 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.